1
FMN Fe--S FMNH 2 2H + MITOCHONDRIAL MATRIX 2e - 4H + 3H + Cytoplasm Cytoplasmic Membrane 4H + 2H + 1.6.5.3 NADH+H + 2H + 2H + ADP Pi I 2H + Fe--S SUCCINATE FUMARATE FAD 1.3.5.1 Fe-S and Cytochromes 1.10.2.2 2H + 2e - III 1.9.3.1 Cu and Cytochromes 2H + Cyt.c 2H + H O 2 IV ADP 3.6.1.3 Pi 3.6.1.34 ATP II UQ UQH2 M I T O C H O N D R IA L IN N E R M E M B R A N E 2H + Mit o c h ondria l O ut e r Membra ne Mito ch ondria l Inne r Membra ne 4.1.1.39 Fixation CO 2 Ribulose-1:5-bis-P H OH OH C C H CO CH O 2 P POCH 2 P680 P700 2H O 2 H + H + H + H + 2H + H + H + H + H + H + H + Thylakoid Lumen H + 2H + 2e* 2e* + T r a n slo c a t e d p r o t o n s Mg ++ 2e * O O 2 2 e - Chloroplast Stroma PC - Thylakoid Membrane Mn PHOTO- Cyt. ADP+Pi 3.6.1.34 Ferredoxin b f Chloroplast Stroma Membrane ATP 3H + 2H + 2H + PC 3.6.1.3 3H + Glyceraldehyde HOCH CH(OH)CHO 2 4.1.2.13 NADP PQ PQH 2 SYSTEM II PHOTO- Pheophytin Chlorophyll Thylakoid To Brain - A M I N O A C I D S P Y R I M I D I N E S P U R I N E S C A T E C H O L A M I N E S A R O M A T I C A M I N O A C I D S STEROIDS hv VISION P O R P H Y R I N S S T E R O I D S I S O P R E N O I D S P H O S P H O L I P I D S L I P I D D E G R A D A T I O N L I P I D B I O S Y N T H E S I S P H O T O S Y N T H E S I S P E N T O S E S H E X O S E S P O L Y S A C C H A R I D E S CO CH CH(NH )COO 2 3 + FOLIC ACID C1 POOL VALINE ATP ATP 4.1.1.4 1.1.1.30 CH COCH 3 3 CH COCH COO 3 2 CH CH(OH)CH COO 3 2 3-OH-Butyrate Acetone Acetoacetate KETONE BODIES HYALURONIC ACID DERMATAN BLOOD GROUP SUBSTANCES PEPTIDO- GLYCAN N-Ac-Neuraminate (Sialate) UDP- Iduronate UDP-N-Ac- Galactosamine UDP- Galacturonate GDP-Fucose TDP-Rhamnose ADP- Glucose UDP-Glucose TDP-4-Oxo- 6-deoxyglucose MANNOSE CHITIN CHONDROITIN PECTIN ALGINATES INULIN CELLULOSE O-ANTIGENS STARCH GLYCOGEN LACTOSE GALACTOSE O OH HO OH OH CH 3 O OPPT O OH OH O OH ACNH HO OH O OH HO OPPU NHAC OH OH OH OH HO OH NHCOCH OH HO O OPPG CH OH 2 HO P UDP-N-Ac- Glucosamine pyruvate N-Ac-Mannosamine-6-P UDP-Glucuronate GDP-Mannose N-Ac-Mannosamine UDP-N-Ac-Glucosamine N-Ac-Glucosamine-6-P Sorbitol Fructose-1-P Erythrose-4-P 3-Dehydrogulonate L-Xylose L-Lyxose D-Xylulose D-Ribose Ribitol L-Arabitol L-Xylulose L-Ribulose L-Ribulose-5-P L-Xylulose-5-P L-Arabinose Xylitol D-Xylose D-Arabinose D-Ribulose ASCORBATE 2, 3-Dioxogulonate N-Ac-Glucosamine-1-P Inositol-P Inositol Glucuronate Gulonate Gulonolactone 2-Oxogulonolactone Fructose 6-P-Gluconate D-Ribulose-5-P D-Xylulose-5-P Mannose-1-P GDP-Glucose TDP-Glucose UDP-Galactose Galactose-P Glucose-1-P Glucose-6-P Fructose-6-P Fructose- 1:6-bis-P OH H H H O HOCH 2 C C C C CO OH OH H OH H H O HOCH 2 C C C CO CO OH H H OH H C C OH CO P-Ribosyl amine Glycerate 2, 3-Diphospho- glycerate 3-P-Glyceraldehyde 1:3-bis-P-Glycerate 3-P-Glycerate 2-P-Glycerate P-enolpyruvate Inositol CH OH 2 CH OH 2 HOCH CH OH 2 CH O 2 HOCH P Glycerol PYRUVATE UDP-Galactose UDP-Sugars CH CH OH 3 2 ETHANOL Dihydroxy- acetone-P (Glycerone-P) Glucosamine-6-P Phospho- serine Chain elongation Mitochondrial Serine Serine Indole-3-glycerol-P 3-Deoxy-D-arabino- heptulosonate-7-P Indoleacetate (Auxin) Indoxyl Formylkynurenine Kynurenine 3-Hydroxy kynurenine 3-Hydroxy anthranilate 2-Amino-3-carboxy muconate semialdehyde NH OH Tryptamine 1-(o-Carboxy phenylamino) 1-deoxyribulose-5-P N-(5-P-Ribosyl) anthranilate Anthranilate Catechol NH Indole- acetaldehyde NH CH CHO 2 Indolepyruvate N H C-CH(OH)CH(OH)CH O 2 P CH 2-Aminomuconate- 6-semialdehyde CH CH NH 2 2 2 NH 1.2.3.7 4.1.1.43 3.5.1.9 3.7.1.3 4.2.1.20 1.13.11.6 4.1.1.45 2.4.2.18 4.6.1.4 4.1.1.48 1.14.13.9 4.6.1.3 Dehydro- quinate 4.2.1.10 1.1.1.25 2.5.1.19 Shikimate-3-P Shikimate-5 enolpyruvate 3-P Chorismate PEP 2.7.1.71 1.4.1.19 Homogentisate Phenylpyruvate Cinnamate Coumarate Prephenate 2-Amino muconate Fumarate Aspartate GLYCINE Sarcosine Hydroxy- pyruvate P-Hydroxy- pyruvate SERINE Imidazole glycerol-P P-Ribosyl-ATP P-Ribosylformimino 5-aminoimidazole- carboxamide-R P Formimino glutamate Imidazolone propionate Urocanate Cystathionine Homocysteine Phosphoadenylyl- sulphate (PAPS) CH (NH )COO 2 3 + Histidinol-P Histidinol Histidinal 3.1.3.15 2.6.1.9 1.1.1.23 3.6.1.31 5.3.1.16 2.4.2.17 Asparagine ALANINE 3-Sulphinyl pyruvate Oxobutyrate 2-Aceto-2- hydroxy- butyrate O-Phospho- homoserine HO SCH CH NH 2 2 2 2 Hypotaurine HO SCH CH NH 3 2 2 2 Taurine Glutamate γ-Glutamylcysteine Glutathione Glycine Cysteine ß-Alanine Cysteate S-Adenosyl homocysteine 4.2.99.2 1.1.1.86 4.2.1.9 1.1.1.86 4.2.1.9 2.6.1.32 4.1.3.18 2-Methylaceto- acetyl-CoA 2-Acetolactate 2-3-Dihydroxy isovalerate 2-Oxo- isovalerate 3-Hydroxy- isobutyrate 3-Hydroxy- Isobutyryl-CoA Methyl acrylyl-CoA 2-Methyl-3- hydroxy- butyryl-CoA Tiglyl-CoA 2 Methylbutyryl- CoA 2:3-Di-OH- 3-methylvalerate 2-Oxo-3-methyl valerate Isobutyryl-CoA Cysteine sulphinate 4.2.99.9 2-Isopropyl- malate CH CH COCOO 3 2 + CH CH(NH )COO 3 3 CH CH(OH)COO 3 HO SCH COCOO 2 2 OCH COCOO 2 P OCH CH(NH )COO 2 3 P HOCH COCOO 2 HOCH CH(NH )COO 2 3 + + OH CH COCOO 2 COO OH OH O COO OH OH HO P COO OH OH O CH 2 P COO O-C-COO OH O OH OOC CH COCOO 2 N H HOC-CH(OH)CH(OH)CH 2 OP CH COO NH 2 COO OH NH 2 COO COO OCH OOCCH NHCH 2 3 CH (CH ) COS-ACP 3 2 14 CH (CH ) COSCoA 3 2 14 CH (CH ) CH=CHCO-S-ACP 3 22 CH CH=CHCO-S-ACP 3 CH CH(OH)CH COS-ACP 3 2 COSCoA Linoleate Oleoyl-CoA Stearoyl-CoA Dehydrostearoyl-CoA OH-Stearoyl-CoA Oxostearoyl-CoA Palmitoyl-ACP Palmitoyl-CoA ACYL-ACP 2, 3-Enoyl-ACP 3, 4-Decenoyl-ACP 2, 3-Decenoyl-ACP 3-OH-Acyl-ACP 3-Oxoacyl-ACP 3-Oxo-Decanoyl-ACP 3-Oxo-Hexanoyl-ACP 3-OH-Hexanoyl-ACP 2, 3-Hexenoyl-ACP Butanoyl-ACP Crotonoyl-ACP 3-OH-Butanoyl-ACP Acetoacetyl-ACP Hexanoyl-ACP 3-OH-Decanoyl-ACP Decanoyl-ACP Palmitoleoyl-ACP γ-Linolenate Arachidonate Leukotriene B4 COSCoA CO-S-ACP Thromboxane B2 HOOCCH CO-S-ACP 2 Malonyl-ACP HOOCCH CO-SCoA 2 Malonyl-Co-A CH CO-S-ACP 3 Acetyl-ACP CH O-CO-R 2 CH OH 2 R’-CO-OCH FATTY ACID ACYL-CoA (Cytosol) CH O-CO-R 2 CH O 2 R’-CO-OCH P Cardiolipin Phosphatidylglycerol Acetylcholine Glycerophosphocholine Lysolecithin Choline plasmalogen CDP-choline Choline-P Mevaldate CH (CH ) CH=CHCH(OH)CHCH OH 3 2 12 2 Dehydrosphinganin Sphinganin 4-Sphingenin Psychosine Acyl-CoA Acyl-CoA Cerebroside Galactose CH (CH ) CH=CHCH(OH)CHCH O- 3 2 12 2 NHCOR Isopentenyl-PP (C5) Dimethylallyl-PP (C5) Geranyl-geranyl-PP (C20) Farnesyl-PP (C15) Squalene (C30) Geranyl-PP (C10) Desmosterol Zymosterol Lanosterol CH C = CHCH O 3 2 PP CH 3 Ceramide Gangliosides NHCOR CH O 2 PP OPP CH 2 CHOLESTEROL CH C(OH)CH CH OH 3 2 2 CH COO 2 CH C(OH)CH CHO 3 2 CH COO 2 NADP + Dehydroascorbate OH H O HOCH 2 C C C C CO OH H OH OH H O HOCH 2 C C CO CO CO H NAD+ Pi ADP Phytoene (C40) Lycopene (C40) ß-CAROTENE (C40) Rhodopsin Metarhodopsin Retinoate trans-Retinal 11-cis-Retinol trans-Retinol (Vitamin A) Retinol esters Dark Light Ubiquinone (Coenzyme Q) Menaquinone Plastoquinone Phylloquinone (Vitamin K) Opsin CHO CH OH 2 CHO CH OH 2 CH 3 CH O 3 CH O 3 n O O O O Phytol (C20) α-Tocopherol (Vitamin E) 5-Amino levulinate Porphobilinogen Uroporphyrinogen III Coproporphyrinogen III Protoporphyrinogen IX HEME Quinolinate Quinolinate- nucleotide Nicotinate- nucleotide Desamino-NAD 5-Hydroxy- tryptophan 5-Hydroxytryptamine (SEROTONIN) N-Acetyl-5-O-methyl-serotonin (MELATONIN) NH CH CH NHCOCH 2 2 3 HO NH CH CH NHCOCH 2 2 3 CH O 3 NICOTINATE N-Acetyl-serotonin 2.4.2.19 Dopamine Dopa Dopaquinone THYROXINE MELANIN OH OH CHOHCH NHCH 2 3 OH OH CHOHCH NH 2 2 4-OH-3-Methoxy- phenylglycol CHOHCH NH 2 2 OH OCH 3 OCH 3 CHOHCH OH 2 OH OCH 3 4-OH-3-Methoxy- D-mandelate Cyclic AMP ATP Dephospho-Coenzyme A 4-P-Pantetheine 4-P-Pantothenylcysteine 4-P-Pantothenate Pantoate 6.3.2.1 1.1.1.169 3.5.1.22 2.7.1.33 NH N H O O O O CH OH 2 OH OCH 3 CH(OH)COO H 2 NH 3 + CH-COO C O O COO N Ribose- P N + COO NH CH COO 2 O OH CH O 2 P NHCOCH NH 2 2 OH Formyl glycinamide-R P Urea Formyl glycinamidine-R P Allantoate Allantoin URATE ADP Xanthine Hypoxanthine Inosine Adenine Adenylo- succinate 5-Amino imidazole-R P 5-Amino-4-imidazole carboxylate-R P 5-Amino-4-imidazole (N-succinylcarboxamide)-R P 5-Aminoimidazole carboxamide-R P Formylamido- imidazole- carboxamide-R P H NCONH 2 2 HN HC 2 CHO NH RP NH C C C O C CO OC NH NH H N HN H C C O C CH OC NH N N HN Carbamoyl ß-alanine Dihydro- uracil Uracil d-ADP d-ATP GTP GDP XANTHOSINE-P (XMP) TTP TDP ß-Ureido isobutyrate Dihydro thymine Thymine d-UMP d-CMP d-CDP CDP Carbamoyl aspartate Dihydro orotate Orotate Orotidine-P Uridine-P (UMP) UDP 3-Amino- isobutyrate CH C NH 2 CH OC NH N CH C O CH OC N H HN CH-CH 3 C O OC NH HN CH 2 CH 2 CH 2 C O OC NH HN C O CH OC NH HN C CH 3 Methylmalonyl semialdehyde OHCCHCOO CH 3 CH 2 C O CH-COO OC NH HN CH C O C-COO OC NH HN H NCONHCH CH COO 2 2 2 C C C CH RP HC NH NH OOC-CH-CH COO 2 N N N CHO NH RP NH OC HC 2 2.7.7.43 3.1.3.29 1.1.1.158 5.1.3.13 2.7.1.38 3.2.1.23 3.1.3.29 4.1.3.20 2.7.1.60 5.1.3.14 5.1.3.7 5.1.3.1 2.7.1.4 5.4.2.3 3.1.1.17 1.1.1.49 2.7.1.1 1.1.1.21 2.7.7.23 3.1.3.25 1.13.99.1 1.1.1.19 1.1.3.8 5.3.1.3 2.7.1.53 1.1.1.9 2.7.1.15 2.7.1.17 5.1.3.4 5.1.3.1 2.2.1.2 4.1.2.13 2.7.1.11 2.7.1.47 2.2.1.1 1.2.1.12 1.1.1.29 1.1.1.95 1.3.1.35 1.14.99.25 2.3.1.41 2.3.1.41 2.3.1.41 1.1.1.100 5.3.99.5 4.2.1.60 5.3.99.3 1.14.99.1 1.13.11.34 1.3.1.10 1.3.1.9 1.14.99.5 1.3.1.9 4.2.1.61 4.2.1.60 4.2.1.60 4.2.1.59 4.2.1.58 1.3.1.9 1.3.1.9 6.2.1.3 3.1.2.20 1.1.1.100 5.3.1.1 HOOC-COOH Oxalate Glycolate HOCH CHO 2 Glycol aldehyde Ethanolamine-P 2.7.1.30 2.3.1.7 3.1.3.4 2.7.1.107 3.7.1.2 4.1.3.5 2.7.8.8 2.1.1.17 2.1.1.71 1.3.1.35 2.7.8.2 3.1.4.3 3.1.4.4 2.7.7.15 3.1.1.5 3.1.4.2 2.7.1.32 2.7.1.82 2.6.1.2 1.4.1.1 4.1.1.1 2.3.1.50 1.1.1.102 3.1.4.12 2.7.8.3 2.4.1.62 3.2.1.46 5.2.1.3 1.2.1.36 2.3.1.76 3.1.1.21 5.2.1.7 5.4.99.7 1.14.99.7 4.3.1.8 4.2.1.75 4.1.1.37 1.3.3.3 1.3.3.4 4.99.1.1 2.5.1.29 2.4.1.47 4.1.1.28 2.3.1.5 2.1.1.4 6.3.5.1 6.3.1.5 2.4.2.11 2.7.7.18 2.6.1.5 1.13.11.5 2.1.1.28 2.1.2.2 6.3.3.1 3.5.2.5 1.4.1.10 1.7.3.3 1.1.1.204 1.1.3.22 1.1.3.22 4.1.1.28 4.1.1.21 2.1.2.3 2.4.2.1 1.5.99.2 2.1.1.5 2.6.1.22 3.5.2.3 2.6.1.51 1.4.1.7 3.1.3.3 2.6.1.52 2.1.3.2 ACETATE 2.4.2.4 2.1.1.45 RP CH C O CH OC N HN 1.3.1.14 2.4.2.10 4.1.1.23 2.7.7.7 2.7.7.7 2.7.7.7 1.17.4.1 2.7.7.7 2.7.4.14 4.4.1.1 1.6.4.1 1.13.11.20 4.4.1.8 4.2.1.22 1.1.1.27 4.1.1.29 6.3.2.3 6.3.2.2 1.8.1.3 LACTATE Acetaldehyde 2.7.1.24 2.7.7.3 4.1.1.36 Bile Acids CH CH COSCoA 3 2 Propanoyl-CoA 2.3.1.16 1.1.1.31 2.1.3.1 4.1.1.41 5.1.99.1 6.4.1.3 1.4.3.1 6.3.2.5 2.1.1.14 2.1.1.13 4.6.1.1 CDP-Ethanolamine 1.1.1.35 4.2.1.17 + HO SCH CH(NH )COO 2 2 3 3.5.2.7 NH HN CH OOC CHCH CH COO 2 2 CMP-N-Acetyl neuraminate CDP-diacyl glycerol CHOLINE Malonic semi- aldehyde Ethanolamine Glyoxylate HISTAMINE 2.3.1.46 Homoserine Tyramine Plant Pigments Tannins Maleyl acetoacetate Fumaryl acetoacetate 5.2.1.2 CH COO 2 OH OH OH CH CH NH 2 2 2 OH OH CH CH NH 2 2 2 Hydroxyphenyl pyruvate α-Tocopherol (Vitamin E) LIGNIN d-GTP OH OH OH O HO OH P OPPT CH 3 HO OH OH O NADPH 2.2.1.1 2.7.1.3 1.1.1.45 1.1.1.130 1.10.3.3 1.10.2.1 1.1.1.10 ATP CH CH NH 2 2 2 NH HO 5.4.99.5 1.14.16.1 2.6.1.5 1.13.11.27 Indole 4.1.99.1 1.13.11.11 OH O OH NH C C CH CH O 2 P H H COO NH 2 COO 6.3.5.3 6.3.2.6 4.3.2.2 Guanine DNA 6.3.4.4 4.3.2.2 C C O C CH HC NH N N HN C C O C CH HC NH N N HN 3.5.3.4 2.4.2.1 2.7.7.6 2.7.7.6 2.7.7.6 2.7.7.6 2.7.4.6 2.7.4.3 2.7.4.4 2.7.4.6 2.4.2.15 1.1.1.205 6.3.4.1 6.3.5.2 2.7.4.4 3.5.4.3 3.2.2.2 2.4.2.1 3.1.3.5 3.1.4.6 6.3.4.2 1.17.4.1 1.17.4.1 3.5.4.12 2.7.4.8 2.7.4.9 2.7.4.6 2.4.2.4 1.3.1.2 3.5.2.2 3.5.1.6 3.5.1.6 3.5.2.2 3.5.4.1 Diphospho- mevalonate Mevalonate 3-Oxopentanoyl-CoA 3-Oxoacyl-CoA 3-OH-Acyl-CoA 2, 3-Enoyl-CoA 2, 3-Hexenoyl-CoA 3-OH-Hexanoyl-CoA Acetoacetyl-CoA 3-OH-Butanoyl-CoA Crotonoyl-CoA Pentanoyl-CoA Pentenoyl-CoA 3-OH-Pentanoyl-CoA ACYL-CoA (Mitochondria) 1.1.1.35 1.1.1.35 1.1.1.157 1.3.99.3 1.3.99.3 1.3.99.2 1.1.1.35 Odd C Fatty acids Succinylhomoserine CO 2 TRANSAMINATION 2-OXO ACID Glutamyl-P Glutamine UREA P-Creatine Creatine Creatinine Glycine CITRULLINE Glutamic semialdehyde 2-AMINO ACID Pyrroline-5- carboxylate Glyoxylate Pyruvate 4-Hydroxy- 2-oxoglutarate 4-Hydroxy- glutamate 3-Hydroxy- pyrroline- 5-carboxylate Putrescine H NCH CH CH CH NH 2 2 2 2 2 2 Spermidine Spermine N -Trimethyllysine 6 6 N -Trimethyl- 3-OH-lysine Carnitine Glutaryl-CoA Saccharopine 2-Aminoadipate semialdehyde 2-Aminoadipate 2-Oxoadipate Arginino- succinate Guanidoacetate Methylmalonyl-CoA 4.1.2.12 Aspartyl Semialdehyde 2, 3-Dihydro- dipicolinate 1.2.1.11 4.2.1.52 1.3.1.26 Piperideine- 2, 6-dicarboxylate N-Succinyl- 2-amino-6-oxo- pimelate 2.6.1.17 N-Succinyl-2, 6 diaminopimelate Diamino- pimelate 3.5.1.18 3-Methyl- glutaconyl-CoA (CH ) CHCH COSCoA 32 2 (CH ) CHCH COSCoA 32 2 3-Methyl- crotonyl-CoA Isovaleryl-CoA Oxopantoate HCHO OOCCH C = CHCOSCoA 2 CH 3 CH COCHCOSCoA 3 CH 3 CH CH=CHCOSCoA 3 CH 3 CH CH(OH)CHCOSCoA 3 CH 3 C(OH)CH(OH)COO CH CH 3 2 CH 3 CH = CCOSCoA 2 CH 3 HOCH CHCOS-CoA- 2 CH 3 CH CHCO-SCoA 3 CH 3 C (OH)CH(OH)COO CH 3 CH 3 CH CH CHCOSCoA 3 2 CH 3 CH C = CHCOSCoA 3 CH 3 ATP 4-Aminobutyrate (GABA) 1.3.99.7 1.5.1.2 1.14.11.2 2.6.1.39 1.2.1.31 1.14.11.8 2.5.1.16 2.5.1.22 4.1.3.16 2.6.1.23 1.5.99.8 1.5.1.2 6.4.1.4 1.3.99.10 4.2.1.33 2.6.1.6 1.1.1.85 Oxoleucine COOH (CH ) CHCHCH(OH)COO 32 S-Adenosylmethyl thiopropylamine (Decarboxylated SAM) PROLINE Coenzyme A CH C= CHCH 3 2 CH 3 O CH CH 3 3 HO CH 3 CH 3 CH 3 CH C-CH HO 3 2 2 C PP CH 2 CH C= CHCH O 2 2 PP CH 3 3-P-Glycerol Phosphatidyl ethanolamine CEPHALIN 3.1.4.12 2.7.8.3 Progesterone 1.5.1.12 2.7.3.2 4.3.1.1 4.2.1.17 3.1.2.4 2.6.1.32 4.4.1.15 Acetylserine 2.7.7.4 2.7.1.25 1.8.99.1 Adenylylsulphate (APS) 2.7.1.39 4.4.1.15 4.1.1.29 4.2.99.8 2.3.1.30 P-Ribosyl-PP 1.1.1.1 1.2.1.4 Aspartyl-P 2.7.2.4 5.1.1.7 2.7.1.40 4.1.3.18 4.1.3.18 5.1.99.1 5.4.99.2 4.1.1.71 1.5.1.9 1.14.11.1 CHOLINE 2.1.1.13 1.3.1.2 NHCH CH SH 2 2 NHCH CH CO 2 2 OCH C(CH ) CH(OH)CO 2 32 P ADP- NHCH CH SH 2 2 NHCH CH CO 2 2 OCH C(CH ) CH(OH)CO 2 32 P-ADP- NHCH CH SH 2 2 NHCH CH CO 2 2 OCH C(CH ) CH(OH)CO 2 32 1.4.1.8 1.3.99.3 1.3.99.3 1.4.1.9 4.2.1.18 4.1.1.20 1.3.99.7 1.8.99.2 + CH CO-OCH CH(NH )COO 2 2 3 2.5.1.6 2.1.1.10 2.1.1.20 1.1.1.3 1.1.1.3 4.2.1.18 1.2.1.16 4.1.1.12 4.1.2.5 4.3.1.5 4.2.1.20 2.1.2.1 2.1.1.20 Glyoxylate 2.1.1.6 1.4.3.4 1.14.18.1 1.14.16.2 Hexanoyl-CoA Butanoyl-CoA 1.18.6.1 1.4.1.2 3.5.1.2 6.3.4.16 6.3.5.5 2.7.2.11 2.1.3.3 NO 1.14.13.39 3.5.3.6 3.5.3.1 4.3.2.1 4.1.1.17 2.7.7.41 2.6.1.4 1.1.1.100 1.1.1.8 2.3.1.51 2.3.1.15 2.7.8.5 SO - 4 2 1.14.16.4 NH 2 OOC OOC 4.1.1.25 1.3.1.13 1.3.1.13 2.7.4.6 CYTIDINE- triphosphate (CTP) Cytosine 2.4.2.9 4.1.1.11 2.6.1.18 4.3.1.3 4.2.1.49 3 HSO - 1.1.1.105 2.3.1.41 NADPH 1.1.1.22 2.3.1.4 5.5.1.4 3.2.1.26 3.2.1.48 2.6.1.16 1.1.1.14 2.7.7.34 4.2.1.47 2.4.1.68 2.4.1.69 2.4.1.9 5.3.1.8 2.4.1.11 O OPPU CH OH 2 CH OH 2 HO OH OH HO 2.4.1.21 OXALOACETATE 4.2.1.52 ATP GTP GDP+Pi 1.2.1.18 CITRATE MALATE SUCCINYL-CoA ISOCITRATE 4.2.1.18 4.2.1.3 1.3.5.1 4.2.1.2 1.1.1.37 6.2.1.4 3.1.2.3 1.7.99.4 1.6.6.1 5-Amino levulinate 1.6.6.4 Glycine O CH C CH OC N HN DP CH C O CH OC N HN RPPP OCH 2 H C C H OH OH CH N HN C H C P H O OCH 2 C C H OH H OH C H C C C NH 2 C CH HC N RP(PP) N N N + P NH 2 H O OCH 2 C C H OH H OH C H C C OC C CH HC N RP N N NH P H OCH 2 C C H OH OH CO CH 2 C CONH 2 C CH HC N RP N N NH P + OOCCH N(CH ) 2 33 Betaine Betaine aldehyde 2.4.1.16 5.1.3.6 2.4.1.33 2.7.7.13 5.4.2.8 5.3.1.8 O OH CH OH 2 HO OP HO 2.7.1.28 2.7.1.31 6.3.4.13 5.3.1.1 2.2.1.1 4.1.1.9 3.1.2.11 ß-OH-ß-Methyl- glutaryl-CoA 2.3.1.37 1.4.1.14 6.3.1.2 3.5.1.2 6.3.4.5 5.3.1.6 2.5.1.21 2.1.1.2 3.5.2.10 6.3.2.13 6.3.2.7-10 2.7.7.27 2.7.7.9 3.5.4.10 C C O C CH OC NRP N N H HN C C O C CH N N N HN RP HN 2 C 2.7.4.6 1.17.4.1 2.7.4.6 2.6.1.13 SUCCINATE Carbamoyl-P 2.3.1.9 Carnitine 2.6.1.44 2.6.1.4 CH C(OH)CH COSCoA 3 2 CH COO 2 1.2.3.5 1.1.1.34 2.3.1.16 4.1.3.5 2.3.1.16 4.1.3.4 Glyoxylate 4.1.3.1 HOOCCHO 4.1.3.2 4.1.1.15 2.6.1.19 2.6.1.1 4.2.1.16 Carnosine CH CH NH 2 2 2 C NH N C HC H 4.1.1.22 4.3.1.3 Ubiquinone Plastoquinone D-Ribose-5-P CH CH(NH )COO 2 3 HO + O OH OH HO OPPU COO - O OH OH HO OPPU COO - OH H OH HOCH 2 C C CO H CO COO - O CHOH CHOH AcNH HO OPC O CO - CH OH 2 O CHOH CHOH AcNH HO OH COO CH OH 2 O OH OHHO HO CH O 2 P O OH ACNH HO OH CH O 2 P O O OH HO HO P CH OH 2 O OH OH HO HO CH OH 2 O OH HO OH 3 CH O 2 P O OH HO O NHCOCH 3 P CH OH 2 CH OH 2 CH OH 2 O OH HO OH NH 2 CH O 2 P O OH HO OH OPPU CH OH 2 O O HO OH OH HO P CH OH 2 CH OH 2 O O HO OH OH O OH OH OH CH OH 2 O OH HO OH OH CH 2 CH OP 2 OH H H H OH C C C C OH OH H COO - HOCH 2 H OH OH OH C C C CHO H H H OH OH H C C C CHO H OH OH H OH H C C C CHO H OH H OH H OH C C C CHO OH H HOCH 2 OH H H OH C C C CHO OH H HOCH 2 OH H OH OH C C C CHO H H H OH H OH C C C C OH H H OH COO - POCH 2 OH H OH C C CO H POCH 2 CH OH 2 H OH H C C CO OH CH OH 2 CH OH 2 POCH 2 H OH OH C C CO H CH OH 2 POCH 2 OH H H C C CO OH CH OH 2 POCH 2 H OH OH C C CO H CH OH 2 OH H OH C C CO H CH OH 2 OH H H C C CO OH CH OH 2 H OH OH H C C C H OH CH OH 2 OH H OH OH C C C H H CH OH 2 H OH H OH C C C C OH H H OH CH OH 2 HOCH 2 H OH OH C C CHO H POCH 2 H OH H OH C C C CO OH H CH O 2 P H OH OH OH C C C H H HOCH 2 CH OH 2 H OH OH C C C H CO H HO POCH 2 CH OH 2 P H OH OH C C C H CO H HO CH O 2 P OCH 2 H OH OH C C H C CHO OH H POCH 2 POCH 2 O OH NH 2 OH CH O 2 P CHOHCHO POCH 2 CO HOCH 2 CH O 2 P O OH OO P P OH CH O 2 P CHOHCOOP POCH 2 CHOH POCH 2 COO COO OH O HO OH COO CH (CH ) CH(OH)CH COS-CoA 3 2 14 2 CH (CH ) CH(OH)CH COS 3 2 14 2 CH (CH ) COCH COS-CoA 3 2 14 2 CH (CH ) COCH COS-CoA 3 2 14 2 CH (CH ) COS-CoA 3 2 n+2 CH (CH ) CH=CHCOS-CoA 3 2 14 CH (CH ) 3 2n CH=CHCOS-CoA CH (CH ) 3 25 2 CH=CHCH COSACP CH (CH ) 3 26 CH=CHCOSACP CH (CH ) 3 26 COCH COSACP 2 CH (CH ) 3 26 2 2 CH CH COSACP CH (CH ) 3 22 2 2 CH CH COSACP CH CH CH COSACP 3 2 2 CH (CH ) 3 26 CH(OH)CH COSACP 2 CH CH=CHCO.S-ACP 3 CH (CH ) 3 22 2 COCH COSACP CH 3 COCH COSACP 2 CH (CH ) 3 2n 2 COCH COSACP CH (CH ) 3 2n 2 CH(OH)CH COSACP CH (CH ) 3 22 2 CH(OH)CH COSACP CH (CH ) CH CH COSCoA 3 2 2 2 n CH (CH ) CH=CHCOSCoA 3 2 n CH (CH CH(OH)CH COSCoA 3 2 n CH (CH ) CH CH COSCoA 3 22 2 2 CH (CH ) CH=CHCOSCoA 3 22 CH (CH ) COCH COSCoA 3 2 2 n CH COCH COSCoA 3 2 CH (CH ) CH(OH)CH COSCoA 3 22 2 CH CH(OH)CH COSCoA 3 2 CH CH=CHCOSCoA 3 CH CH CH COSCoA 3 2 2 CH CH CH CH COSCoA 3 2 2 2 CH CH CH=CHCOSCoA 3 2 CH CH CH(OH)CH COSCoA 3 2 2 CH (CH ) COCH COSCoA 3 22 2 CH CH COCH COSCoA 3 2 2 OH OH HO OH O O- CH O-PO 2 CH CHOHCH OH 2 2 O CH 2 CH 2 O R'-CO-OCH CH O-CO-R 2 CH O-PO 2 O- HOCH CH 2 2 NH 3 + POCH CH 2 2 NH 3 + CPP- OCH CH 2 2 NH 3 + O - CH O-CO-R 2 CH O P 2 OCH CH 2 2 NH 3 + CH COCH CH N(CH ) 3 2 2 33 HOCH CH N(CH ) 2 2 33 + CH CH 2 COO (NH ) 3 + OH OH CH CH 2 COO- (NH ) 3 + CO NH 2 CH CH(NH )COO 2 3 + NH OC CO NH OC N H C H HN 2 HC CH N N C RP HN 2 CH C CH OC N N DP NH 2 RPPP CH C CH OC N N NH 2 C C C CH RP(P) HC N N N N NH 2 H NCOO 2 P (CH ) NH 23 2 H N(CH ) NH 2 23 (CH ) NH 24 (CH ) NH 23 2 H N(CH ) NH 2 24 CH -SCH CH CHNH 3 2 2 2 Adenosyl + + CH 3 CH 3 CHCH(NH )COO 3 + C NH N C HC H CH CH(NH )CH OH 2 3 2 + C NH N C HC H CH CH(NH )CH OP 2 3 2 C NH N C H HC CH COCH OP 2 2 + HSCH CH CH(NH )COO 2 2 3 + + SCH CH CH(NH )COO 2 2 3 CH CH(NH )COO 2 3 RP C O C-COO OC N HN CH 2.4.1.23 CH (CH ) CH=CHCH(OH)CHCH OH 3 2 12 2 CH (CH ) CH=CHCH(OH)CHCH OH 3 2 12 2 NH 3 + CH (CH ) CH(OH)CHCH OH 3 2 14 2 NH 3 + CH (CH ) COCHCH OH 3 2 14 2 NH 3 + Galactose CH (CH ) CH=CHCH(OH)CHCH O- 3 2 12 2 CH (CH ) CH=CHCH(OH)CHCH O- 3 2 12 2 NH 3 + NH 3 + 4.1.1.70 H NCONH 2 2 NH 4 + OHCCH N(CH ) 2 33 + C-CH3 C O CH OC N DP HN DP CPP-OCH CH N(CH ) 2 2 33 + OCH CH N(CH ) P 2 2 33 + GTP 2-OXOGLUTARATE 1.2.1.41 4.1.3.8 FUMARATE UDP-N-Ac-Muramate O O CH CH 3 COO- NHAC HO OPPU CH OH 2 4.1.3.20 O OH CH 3 HO HO OPPG 2.7.7.24 2.4.1.22 2.7.7.12 5.1.3.2 5.3.1.4 Sedoheptulose-PP 3.1.1.28 4.2.1.24 N CH 2 CH 2 N N N CH 3 CH 3 CH CH COO CH 2 CH CH 2 HC 3 HC C C H H Fe CH 2 CH 2 COO - - CH 3 CH 3 CH 2 CH 2 CH 2 HC 3 HC 3 N H N H N H N H CH CH HC 2 C C H 2 H 2 - CH 2 CH 2 COO CH 2 CH 2 COO - HC 2 HC 2 CH 2 CH 2 OOC COO HN 2 N H - - OOCCH CH COCH NH 2 2 2 2 - CH 2 HC 2 HC 2 HC 2 H 2 H 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 N H N H N H N H COO COO COO COO C C - - CH 2 CH 2 COO CH 2 CH 2 COO - - - - OOC - OOC - CH 3 CH 3 HC 3 HC 3 HC 2 H 2 H 2 N H N H N H N H CH 2 CH 2 CH 2 CH 2 CH 2 C C COO - CH 2 CH 2 COO CH 2 CH 2 COO - - COO - COO - OOCCOCH CH 2 2 COO - - 1.2.4.2 OOCCH CH COSCoA 2 2 - 1.1.1.41 OOCCH CH COO 2 2 OOCCH=CHCOO OOCCH(OH)CH COO 2 CH COO 2 CHCOO CHOHCOO C(OH)COO CH COO 2 CH COO 2 CH C(OH)CH CH O 3 2 2 PP CH COO 2 OHCCOO HOCH COO 2 NH 2 H NCNHCH COO 2 2 + NH 2 H NCN(CH )CH COO 2 3 2 + NH 2 HNCN(CH )CH COO 3 2 P- + HN C NH CO N CH2 CH 3 OOCCHCH COO 2 H NCNHCH CH CH CH 2 2 2 2 N (NH ) 3 + COO CHCOO HC CH 2 HOCH N OOCCH(OH)CH CH(NH )COO 2 3 + CHCOO CH 2 HOCH HC 2 N H NH CHCOO CH 2 CH 2 CH 2 OOCCH(OH)CH COCOO 2 N CHCOO CH 2 CH 2 CH CH COCOO 3 OHCCOO + H NCONHCH CH CH CH 2 2 2 2 (NH ) 3 COO H NOCCH CH CH 2 2 2 COO (NH ) 3 + R-CO-COO + COO R-CH(NH ) 3 + COO H NOCCH CH 2 2 (NH ) 3 + OOC-CH-COSCoA CH 3 P OOCCH CH 2 COO (NH ) 3 + OOCCH CH CHO 2 2 OHCCH CH 2 COO (NH ) 3 + (CH ) NCH CH(OH)CH COO 33 2 2 + OHCCH CH CH 2 2 + COO (NH ) 3 POOCCH CH CH 2 2 + COO (NH ) 3 OHCCH CH CH CH 2 2 2 COO (NH ) 3 + NH CHCH CH COO 2 2 COO CH CH CH CH CH 2 2 2 2 COO (NH ) 3 + (CH ) N(CH ) 33 23 CH CH(NH )COO 2 3 + + CH 2 C H OOCC N HC CH-COO CH 2 C H 2 CH-COO OOCC N HC 2 OOCCOCH CH CH CH-COO 2 2 2 CH CH 2 2 2 OOCCH CH CONH 2 2 OOCCHCH CH CH CH-COO 2 2 2 OOCCH CH CONH 2 2 CH 2 2 NH 3 + OOCCH-CH CH CH CHCOO 2 2 2 NH 3 + NH 3 + 4.1.1.32 (CH ) CHC(OH)CH 32 2 COOH COO (CH ) CHCH COCOO 32 2 HOCH CHCOO 2 CH 3 CHCOCOO CH 3 CH COC(OH)CH 3 3 COO + POCH CH CH(NH )COO 2 2 3 + HOCH CH CH(NH )COO 2 2 3 + CH CH CH(NH )COO 2 2 3 OOCCH CH 2 COO 2 + CH SH 2 OOCCH(NH )CH CH CONHCHCONHCH COO 3 2 2 2 HOCH C(CH ) COCOO 2 32 HOCH C(CH ) CH(OH)COO 2 32 NHCH CH COO 2 2 HOCH C(CH ) CH(OH)CO 32 ) 2 32 NHCH CH COO 2 2 OCH C(CH ) CH(OH)CO 2 32 P CH CH 3 2 CH 3 CH + CH(NH )COO 3 CH COC(OH)CH CH 3 2 3 COO CHCOCOO CH CH 3 2 CH 3 NHCHCH SH 2 COO NHCH CH CO 2 2 OCH C(CH ) CH(OH)CO 2 32 P + CH SH 2 OOCCH(NH )CH CH CONHCHCOO 3 2 2 + Adenosyl SCH CH CH(NH )COO 2 2 3 + SCH CH CH(NH )COO 2 2 3 + HO SCH CH(NH )COO 3 2 3 + S-CH CH(NH )COO 2 3 S-CH CH(NH )COO 2 3 + HSCH CH(NH )COO 2 3 1.1.1.23 H C NH N C HC CH CHCOO 2 NHCOCH CH NH 2 2 2 + H C NH N C HC CH CH(NH )COO 2 3 CHCH CH COO 2 2 NH N CH OC C CH CHCOO NH N CH CH CH COO 3 N H OOC CH-COO OC NH 2 CH 2 H NCH CH COO 2 2 2 H NCH 2 2 CH 3 CHCOO H NCONHCH CHCOO 2 2 CH 3 C C O CH RP HC N N N HN C C C O CH HCO N N N RP C CH N N HN 2 H C C C O CH N N C C CH N N RP HN 2 HN 2 C O O OP~ ~ P O O O O PO O CH 2 N N N N O OH OH NH 2 HC CH N N N N O O P O O O CH2 OH NH 2 HC CH COO CO NH OC N H C H HN 2 NH 2 OOC-CH-CH COO 2 HNCO C CH N N C RP RP HN 2 OOC C CH N RP N C HN 2 CH=CHCOO OH CH=CHCOO CH COCOO 2 CH 2 P COO OH O O O COO O CH COO 2 O CH COO 2 -OOC OCH 2 CH 2 OH H C P HOCH HCOH OC COO COO HO OH OH O NH 2 COO OCH NH CH COCOO 2 NH CHO CO NH 2 OH CH CH(NH )COO 2 3 + COO COO N + COO COO RP O OH OH HO OPPU COO O OH NHCOCH 3 HO OPPU COO CH OH 2 O O C CH 2 NHAC HO OPPU COO CH OH 2 O OH HO OH OH COO OOCCH N(CH ) 2 32 Dimethylglycine 1.1.99.1 1.2.1.8 COO HO HO COO COO O HO OH COO CH(O ) P POCH2 COO CH(OH) HOCH 2 COO COO CH(O ) P HOCH 2 COO CH =C(O ) 2 P COO CH CO 3 COO 4.1.3.7 OOCCOCH COO 2 CONH 2 Ribose -O - P - O - P - O- Adenosine(P) + N O O O O + COO N Ribose - O - P - O - P - O -Adenosine O O O O I I I I OH O CH CH 2 COO (NH ) 3 + Epinephrine (Adrenaline) Norepinephrine (Noradrenaline) Normetepinephrine (Normetadrenaline) HOCH CH N(CH ) 2 2 33 + Adenosyl + + SCH CH CH(NH )COO 2 2 3 (CH ) N(CH ) 33 23 CH CH(NH )COO 2 3 + + OH OOCCH CH CH COSCoA 2 2 2 OOCCH CH CH NH 2 2 2 2 OOCCH CH CH COCOO 2 2 2 OOCCH CH CH CH 2 2 2 COO COO (NH ) 3 + HO H HO H H HO H HO H Prostaglandin PGE 2 OH HOCH 2 C C CO C COO OH H OH H H - COO O R'-CO-OCH CH O-CO-R 2 CH O POCMP 2 O CH CH N(CH ) 2 2 3 + O HOCH CH OPO 2 CH OH 2 O- CH OPO 2 O CH OCH=CHR 2 CH CH N(CH ) 2 2 33 + O- CH OPO 2 O R'-CO-OCH CH O-CO-R 2 3.1.1.32 CH CH N(CH ) 2 2 33 + O- O HOCH CH OPO 2 CH O-CO-R 2 CH CH N(CH ) 2 2 33 + O- CH CH(NH )COO 2 3 + + C NH N C HC H CH CH(NH )CHO 2 3 HS 11-cis-Retinal Pi ADP ATP NADP + GDP- Mannuronate Mannose-6-P Dehydro- shikimate Shikimate RNA d-GDP d-CTP GUANOSINE-P (GMP) ß-Alanine P-Ribosyl-AMP P-Ribulosylformimino 5-aminoimidazole- carboxamide-R P Imidazole acetol-P HS HSO - PANTOTHENATE 3-Isopropyl- malate Succinic semialdehyde N 2 NO 3 _ NO 2 _ CO 2 2.4.1.17 Diacyl glycerol ACETYL-CoA CH COSCoA 3 2.3.1.6 1.1.1.39 1.14.12.1 1.4.4.2 CH CHO 3 3.5.4.19 4.2.1.19 3.3.1.1 4.1.1.12 4.1.2.5 OHCCH COO 2 6.3.5.4 2.1.4.1 2.4.99.7 5.1.3.12 1.1.1.132 4.2.1.46 2.7.1.7 2.4.1.29 2.4.1.21 2.4.1.13 2.4.1.1 etc. 5.4.2.2 2.7.1.6 2.7.7.10 3.1.1.18 4.1.1.34 2.7.1.47 2.7.1.16 3.1.3.9 ADP P-Glucono lactone 1.1.1.44 O O OH HO OH CH O 2 P PHENYLALANINE TYROSINE TRYPTOPHAN INOSINE-P (IMP) THYMIDINE-P HISTIDINE URIDINE- triphosphate (UTP) CYSTINE CYSTEINE ISOLEUCINE LEUCINE LYSINE ASPARTATE ORNITHINE ARGININE HYDROXY PROLINE PHOSPHATIDYL SERINE Phosphatidyl inositol LECITHIN SPHINGOMYELIN STEROIDS Pregnenolone CHLOROPHYLL HEMOGLOBIN 2.7.6.1 2.4.2.14 6.3.4.7 5.3.1.9 3.1.3.11 2.7.2.3 H OH OH C C C H CO OH C H H OH POCH 2 CH O 2 P 5.4.2.1 ADP 4.2.1.11 Endoplasmic Reticulum 1.1.1.100 3.1.1.3 Phosphatidate 2.3.1.39 4.2.1.17 4.2.1.17 4.2.1.55 1.1.1.79 1.2.1.21 1.4.3.8 1.1.1.32 2.7.1.36 2.7.4.2 4.1.1.33 2.5.1.1 2.5.1.10 2.7.8.5 2.7.8.1 4.1.1.65 2.7.7.14 1.3.99.7 PO O CH (CH ) CH=CHCH(OH)CHCH O 3 2 12 2 NHAcyl CH CH N(CH ) 2 2 33 + O- 3.5.1.23 1.13.11.21 2.5.1.32 1.1.1.105 2.4.2.19 1.2.1.32 METHIONINE 4.1.3.27 4.2.1.51 1.14.17.1 1.14.18.1 1.14.13.11 Glycinamide- ribosyl-P 4.2.1.22 3-Oxohexanoyl-CoA THREONINE 1.2.1.25 1.2.1.25 1.2.1.25 1.5.1.7 - 10 GLUTAMATE 1.7.7.1 2.3.1.38 ATP NADH SUCROSE ADENOSINE-P (AMP) Triacylglycerol FAT RNA CH 2 OC-COO OH COO CH CH 2 COO (NH ) 3 + T R A N S L O C A T E D P R O T O N S 3H + 1H + 1H + GLYCOPROTEINS GANGLIOSIDES MUCINS 2.7.1.2 4.1.2.- 2.6.1.- Some other pathways occurring in the mitochondria are identified by a pale yellow background Small numbers refer to the IUBMB Enzyme Commission Reference Numbers for Enzymes L E G E N D Pentose Phosphate Pathway Carbohydrates Biosynthesis Degradation Amino Acids Biosynthesis Degradation Lipids Biosynthesis Degradation Purines & Pyrimidines Biosynthesis Degradation Vitamins, Co-Enzymes & Hormones Photosynthesis Dark Reactions Human Metabolism is identified as far as possible by black arrows Biosynthesis Degradation GLUCOSE O-Acyl-carnitine O-Acyl-carnitine + NAD OH O - - R'-CO-OCH R'-CO-OCH O HCO-CO-R CH CH(OH)CH O-P-OCH 2 2 2 CH O-CO-R’ 2 O R'-CO-OCH O- CH O-CO-R 2 CH O-PO 2 O- 2.7.8.11 H NCH CH CH CH 2 2 2 2 COO (NH ) 3 + 2.3.1.20 NH 2 + + H NCNHCH CH CH CH 2 2 2 2 COO (NH ) 3 H OH H OH C C C CO OH H CH OH 2 R-CH 2 COO CH O-CO-R 2 CH O-CO-R" 2 R’-CO-OCH OH O CH CHNH 2 3 + O R'-CO-OCH CH O-CO-R 2 CH O PO 2 COO OOCCH CH CH 2 2 COO (NH ) 3 + OOCCH CH(NH )COO 2 3 + CH CH(OH)CH(NH )COO 3 3 O OH HO OH OH CH OH 2 CH OH 2 NH CH O-CO-R 2 COMPARTMENTATION The "BACKBONE" of metabolism involves GLYCOLYSIS, the TCA CYCLE and OXIDATIVE PHOSPHORYLATION. It is a major source of energy (ATP) and is the origin and termination of most of the pathways. GLYCOLYSIS occurs in the CYTOPLASM. The TCA CYCLE is in the MITOCHONDRIAL MATRIX. OXIDATIVE PHOSPHORYLATION (ATP SYNTHESIS) spans the MITOCHONDRIAL INNER MEMBRANE. This last part has been redesigned to illustrate the activation of ATP-synthase and formation of ATP - driven by the electromotive translocation of protons across the mitochondrial inner membrane. A similar compartmentation occurs in the chloroplast, where light-driven proton translocation across the inner thylakoid membrane initiates synthesis of the ATP necessary for Photosynthesis. In both cases flow of electrons and protons is shown in red or blue arrows Electron Flow Proton Flow HOCH 2 HOCH 2 HOCH 2 HOCH 2 HOCH 2 HOCH 2 HOCH 2 HOCH 2 HOCH 2 HOCH 2 HOCH 2 HOCH 2 SYSTEM I NH (H N)(CH ) 4 2 CH(NH )COO 3 CH(NH 3 + + CH 3 H N 1.3.1.13 + CH - 3 CH - 3 + (CH ) CHCH 32 2 CH(NH )COO 3 HC 3 HC 3 R'-CO-OCH O- 4.1.1.28 2.7.1.15 Ribokinase 2.7.1.16 Ribulokinase 2.7.1.17 Xylulokinase 2.7.1.19 Phosphoribulokinase 2.7.1.24 Dephospho-CoA kinase 2.7.1.25 Adenylylsulfate kinase 2.7.1.28 Triokinase 2.7.1.30 Glycerol kinase 2.7.1.31 Glycerate kinase 2.7.1.32 Choline kinase 2.7.1.33 Pantothenate kinase 2.7.1.34 Pantetheine kinase 2.7.1.36 Mevalonate kinase 2.7.1.39 Homoserine kinase 2.7.1.40 Pyruvate kinase 2.7 1.47 D-Ribulokinase 2.7.1.53 l-Xylulokinase 2.7.1.60 N-Acylmannosamine kinase 2.7.1.71 Shikimate kinase 2.7.1.80 Pyrophosphate—serine phosphotransferase 2.7.1.82 Ethanolamine kinase 2.7.1.107 Diacylglycerol kinase 2.7.2.3 Phosphoglycerate kinase 2.7.2.4 Aspartate kinase 2.7.2.6 Formate kinase 2.7.2.11 Glutamate 5-kinase 2.7.3.2 Creatine kinase 2.7.4.2 Phosphomevalonate kinase 2.7.4.3 Adenylate kinase 2.7.4.4 Nucleoside-phosphate kinase 2.7.4.6 Nucleoside-diphosphate kinase 2.7.4.8 Guanylate kinase 2.7.4.9 dtmp kinase 2.7.4.14 Cytidylate kinase 2.7.6.1 Ribose-phosphate pyrophosphokinase 2.7.7.3 Pantetheine-phosphate adenylyltransferase 2.7.7.4 Sulfate adenylyl transferase 2.7.7.6 RNA nucleotidyltransferase (DNA-directed) 2.7.7.7 DNA nucleotidyltransferase (DNA-directed) 2.7.7.9 UTP—glucose-1-phosphate uridylyltransferase 2.7.7.10 UTP—hexose-1-phosphate uridylyltransferase 2.7.7.12 UDP glucose—hexose-1-phosphate uridylyltransferase 2.7.7.13 Mannose-1-phosphate guanylyltransferase 2.7.7.14 Ethanolamine-phosphate cytidylyltransferase 2.7.7.15 Choline-phosphate cytidylyltransferase 2.7.7.18 Nicotinate-nucleotide adenylyltransferase 2.7.7.23 UDP-N-acetylglucosamine pyrophosphorylase 2.7.7.24 Glucose-1-phosphate thymidylyltransferase 2.7.7.27 Glucose-1-phosphate adenylyltransferase 2.7.7.34 Glucose-1-phosphate guanylyltransferase 2.7.7.41 Phosphatidate cytidylyltransferase 2.7.7.43 N-Acylneuraminate cytidylyltransferase 2.7.8.1 Ethanolamine phosphotransferase 2.7.8.2 Diacylglycerol cholinephosphotransferase 2.7.8.3 Ceramide cholinephosphotransferase 2.7.8.5 CDPdiacylglycerol—glycerol-3- phosphate 3-phosphatidyltransferase 2.7.8.8 CDPdiacylglycerol—serine O-phosphatidyltransferase 2.7.8.11 CDPdiacylglycerol—inositol 3-phosphatidyltransferase 2.8.3.5 3-Oxoacid CoA-transferase 2.8.3.6 3-Oxoadipate CoA-transferase HYDROLASES 3.1.1.3 Triacylglycerol lipase 3.1.1.4 Phospholipase A2 3.1.1.5 Lysophospholipase 3.1.1.7 Acetylcholinesterase 3.1.1.17 Gluconolactonase 3.1.1.21 Retinyl-palmitate esterase 3.1.1.28 Acylcarnitine hydrolase 3.1.1.31 6-Phosphogluconolactonase 3.1.1.32 Phospholipase A1 3.1.2.1 Acetyl-CoA hydrolase 3.1.2.3 Succinyl-CoA hydrolase 3.1.2.4 3-Hydroxyisobutyryl-CoA hydrolase 3.1.2.11 Acetoacetyl-CoA hydrolase 3.1.2.20 Acyl-CoA hydrolase 3.1.3.2 Acid phosphatase 3.1.3.3 Phosphoserine phosphatase 3.1.3.4 Phosphatidate phosphatase 3.1.3.5 5´-Nucleotidase 3.1.3.9 Glucose-6-phosphatase 3.1.3.11 Fructose-bisphosphatase 3.1.3.15 Histidinol-phosphatase 3.1.3.25 myo-Inositol-1(or 4)-monophosphatase 3.1.3.27 Phosphatidylglycerophosphatase 3.1.3.29 N-Acylneuraminate-9-phosphatase 3.1.3.31 Nucleotidase 3.1.4.2 Glycerophosphocholine phosphodiesterase 3.1.4.3 Phospholipase C 3.1.4.4 Phospholipase D 3.1.4.10 1-Phosphatidylinositol phosphodieterase 3.1.4.12 Sphingomyelin phosphodiesterase 3.2.1.21 ß-Glucosidase 3.2.1.23 ß-Galactosidase 3.2.1.26 ß-Fructofuranosidase 3.2.1.45 Glucosylceramidase 3.2.1.46 Galactosylceramidase 3.2.1.48 Sucrose a-glucosidase 3.2.2.2 Inosine nucleosidase 3.3.1.1 Adenosylhomocysteinase 3.5.1.1 Asparaginase 3.5.1.2 Glutaminase 3.5.1.6 ß-Ureidopropionase 3.5.1.9 Arylformamidase 3.5.1.18 Succinyl-diaminopimelate desuccinylase 3.5.1.22 Pantothenase 3.5.1.23 Ceramidase 3.5.2.2 Dihydropyrimidinase 3.5.2.3 Dihydroorotase 3.5.2.5 Allantoinase 3.5.2.7 Imidazolonepropionase 3.5.2.10 Creatininase 3.5.3.1 Arginase 3.5.3.4 Allantoicase 3.5.3.6 Arginine deiminase 3.5.4.1 Cytosine deaminase 3.5.4.3 Guanine deaminase 3.5.4.6 AMP deaminase 3.5.4.10 IMP cyclohydrolase 3.5.4.12 dCMP deaminase 3.5.4.19 Phosphoribosyl-AMP cyclohydrolase 3.6.1.3 Adenosinetriphosphatase 3.6.1.15 Nucleoside-triphosphatase 3.6.1.31 Phosphoribosyl-ATP pyrophosphatase 3.6.1.34 H+-transporting ATP synthase 3.7.1.2 Fumarylacetoacetase 3.7.1.3 Kynureninase 3.9.1.1 Phosphoamidase LYSASES 4.1.1.1 Pyruvate decarboxylase 4.1.1.3 Oxaloacetate decarboxylase 4.1.1.4 Acetoacetate decarboxylase 4.1.1.9 Malonyl-CoA decarboxylase 4.1.1.11 Aspartate 1-decarboxylase 4.1.1.12 Aspartate 4-decarboxylase 4.1.1.15 Glutamate decarboxylase 4.1.1.17 Ornithine decarboxylase 4.1.1.20 Diaminopimelate decarboxylase 4 1.1.21 Phosphoribosylaminoimidazole carboxylase 4.1.1.22 Histidine decarboxylase 4.1.1.23 Orotidine-5’-phosphate decarboxylase 4.1.1.25 Tyrosine decarboxylase 4.1.1.28 Aromatic-L-amino-acid decarboxylase 4.1.1.29 Sulfoalanine decarboxylase 4.1.1.32 Phosphoenolpyruvate carboxykinase (GTP) 4.1.1.33 Diphosphomevalonate decarboxylase 4.1.1.34 Dehydro-l-gulonate decarboxylase 4.1.1.36 Phosphopantothenoylcysteine decarboxylase 4.1.1.37 Uroporphyrinogen decarboxylase 4.1.1.39 Ribulose-bisphosphate carboxylase 4.1.1.41 Methylmalonyl-CoA decarboxylase 4.1.1.43 Phenylpyruvate decarboxylase 4.1.1.45 Aminocarboxymuconate- semialdehyde decarboxylase 4.1.1.48 Indole-3-glycerol-phosphate synthase 4.1.1.49 Phosphoenolpyruvate carboxykinase (ATP) 4.1.1.50 Adenosylmethionine decarboxylase 4.1.1.65 Phosphatidylserine decarboxylase 4.1.1.71 2-Oxoglutarate decarboxylase 4.1.2.5 Threonine aldolase 4.1.2.12 Ketopantoaldolase 4.1.2.13 Fructose-bisphosphate aldolase 4.1.2.14 2-Dehydro-3-deoxyphosphogluconate aldolase 4.1.3.1 Isocitrate lyase 4.1.3.2 Malate synthase 4.1.3.4 Hydroxymethylglutaryl-CoA lyase 4.1.3.5 Hydroxymethylglutaryl-CoA synthase 4.1.3.7 Citrate (si)-synthase 4.1.3.8 ATP citrate (pro-S)-lyase 4.1.3.16 4-Hydroxy-2-oxoglutarate aldolase 4.1.3.18 Acetolactate synthase 4.1.3.20 N-Acylneuraminate-9-phosphate synthase 4.1.3.21 Homocitrate synthase 4.1.3.22 Citramalate lyase 4.1.3.27 Anthranilate synthase 4.1.99.1 Tryptophanase 4.2.1.2 Fumarate hydratase 4.2.1.3 Aconitate hydratase 4.2.1.4 Citrate dehydratase 4.2.1.9 Dihydroxy-acid dehydratase 4.2.1.10 3-Dehydroxyquinate dehydratase 4.2.1.11 Phosphopyruvate hydratase (enolase) 4.2.1.13 l-Serine dehydratase 4.2.1.16 Threonine dehydratase 4.2.1.17 Enoyl-CoA hydratase 4.2.1.18 Methylglutaconyl-CoA hydratase 4.2.1.19 Imidazoleglycerol-phosphate dehydratase 4.2.1.20 Tryptophan synthase 4.2.1.22 Cystathionine B-synthase 4.2.1.24 Porphobilinogen synthase 4.2.1.33 3-Isopropylmalate dehydratase 4.2 1.46 dTDPglucose 4,6-dehydratase 4.2.1.47 GDPmannose 4,6-dehydratase 4.2.1.49 Urocanate hydratase 4.2.1.51 Prephenate dehydratase 4.2.1.52 Dihydrodipicolinate synthase 4.2.1.55 3-Hydroxybutyryl-CoA dehydratase 4.2.1.58 Crotonoyl-[acyl-carrier-protein] hydratase 4.2.1.59 3-Hydroxyoctanoyl-[acyl-carrier protein] dehydratase 4.2.1.60 3-Hydroxydecanoyl-[acyl-carrier protein] dehydratase 4.2.1.61 3-Hydroxypalmitoyl-[acyl-carrier protein] dehydratase 4.2.1.75 Uroporphyrinogen-III synthase 4.2.1.80 2-Oxopent-4-enoate hydratase 4.2.99.2 Threonine synthase 4.2.99.8 Cysteine synthase 4.2.99.9 O-Succinylhomoserine (thiol)-lyase 4.3.1.1 Aspartate ammonia-lyase 4.3.1.2 Methylaspartate ammonia-lyase 4.3.1.3 Histidine ammonia-lyase 4.3.1.5 Phenylalanine ammonia-lyase 4.3.2.1 Argininosuccinate lyase 4.3.2.2 Adenylosuccinate lyase 4.4.1.1 Cystathionine g-lyase 4.4.1.8 Cystathionine ß-lyase 4.4.1.15 D-Cysteine desulfhydrase 4.6.1.1 Adenylate cyclase 4.6.1.3 3-Dehydroquinate synthase 4.6.1.4 Chorismate synthase 4.99.1.1 Ferrochelatase ISOMERASES 5.1.3.1 Ribulose-phosphate 3-epimerase 5.1.3.2 UDPglucose 4-epimerase 5.1.3.4 l-Ribulose-phosphate 4-epimerase 5.1.3.6 UDPglucuronate 4-epimerase 5.1.3.7 UDP-N-acetylglucosamine 4-epimerase 5.1.3.12 UDPglucuronate 5´-epimerase 5 1.3.13 dTDP-4-Dehydrorhamnose 3,5-epimerase 5.1.3.14 UDP-N-acetylglucosamine 2-epimerase 5.1.99.1 Methylmalonyl-CoA epimerase 5.2.1.2 Maleylacetoacetate isomerase 5.2.1.3 Retinal isomerase 5.2.1.7 Retinol isomerase 5.3.1.1 Triose-phosphate isomerase 5.3.1.3 Arabinose isomerase 5.3.1.4 l-Arabinose isomerase 5.3.1.5 Xylose isomerase 5.3.1.6 Ribose-5-phosphate isomerase 5.3.1.8 Mannose-6-phosphate isomerase 5.3.1.9 Glucose-6-phosphate isomerase 5.3.1.16 N-(5´-Phospho-d-ribosylformimino)- 5-amino-1-(5´´-phosphoribosyl)- 4-imidazolecarboxamide isomerase 5.3.3.2 Isopentenyl-diphosphate ³-isomerase 5.3.99.3 Prostaglandin-E synthase 5.3.99.5 Thromboxane-A synthase 5.4.2.1 Phosphoglycerate mutase 5.4.2.2 Phosphoglucomutase 5.4.2.3 Phosphoacetylglucosamine mutase 5.4.2.8 Phosphomannomutase 5.4.3.8 Glutamate-1-semialdehyde 2,1-aminomutase 5.4.99.2 Methylmalonyl-CoA mutase 5.4.99.5 Chorismate mutase 5.4 99.7 Lanosterol synthase 5.5.1.4 myo-Inositol- l-phosphate synthase LIGASES 6.2.1.3 Long-chain-fatty-acid-CoA ligase 6.3.1.1 Aspartate—ammonia ligase 6.3.1.2 Glutamate—ammonia ligase 6.3.1.4 Aspartate—ammonia ligase (ADP-forming) 6.3.1.5 NAD+ synthetase 6.3.2.1 Pantoate—ß-alannine ligase 6.3.2.2 Glutamate—cysteine ligase 6.3.2.3 Glutathione synthase 6.3.2.5 Phosphopantothenate—cysteine ligase 6.3.2.6 Phosphoribosylaminoimidazole- succinocarboxamide synthase 6.3.2.7 UDP-N-Acetylmuramoyl-l-alanyl- d-glutamate—lysine ligase 6.3.2.8 UDP-N-acetylmuramate—alanine ligase 6.3.2.9 UDP-N-acetylmuramoylalanine— d-glutamate ligase 6.3.2.10 UDP-N-acetylmuramoylalanyl- d-glutamyl-lysine—d-alanyl-d-alanine ligase 6.3.2.13 UDP-N-Acetyl muramoylalanyl-d- glutamate—2,6-diaminopimelate ligase 6.3.3.1 Phosphoribosylglycinamidine cyclo-ligase 6.3.4.1 GMP synthase 6.3.4.2 CTP synthase 6.3.4.3 Formate—tetrahydrofolate ligase 6.3.4.4 Adenylosuccinate synthase 6.3.4.5 Argininosuccinate synthase 6.3.4.7 Ribose-5-phosphate—ammonia ligase 6.3.4.13 Phosphoribosylamine—glycine ligase 6.3.4.16 Carbamoyl-phosphate synthase (ammonia) 6.3.4.17 Formate—dihydrofolate ligase 6.3.5.1 NAD+ synthetase (glutamine-hydrolysing) 6.3.5.2 GMP synthetase (glutamine-hydrolysing) 6.3.5.3 Phosphoribosylformylglycinamidine synthetase 6.3.5.4 Asparagine synthase (glutamine-hydrolysing) 6.3.5.5 Carbamoyl-phosphate synthase (glutamine-hydrolysing) 6.4.1.1 Pyruvate carboxylase 6.4.1.2 Acetyl-CoA carboxylase 6.4.1.3 Propionyl-CoA carboxylase 6.4.1.4 Methylcrotonoyl-CoA carboxylase OXIDOREDUCTASES 1.1.1.1 Alcohol dehydrogenase 1.1.1.3 Homoserine dehydrogenase 1.1.1.8 Glycerol-3-phosphate dehydrogenase 1.1.1.9 D-Xylulose reductase 1.1.1.10 l-Xylulose reductase 1.1.1.14 l-Iditol dehydrogenase 1.1.1.19 Glucuronate reductase 1.1.1.21 Aldehyde reductase 1.1.1.22 UDPglucose dehydrogenase 1.1.1.23 Histidinol dehydrogenase 1.1.1.25 Shikimate dehydrogenase 1.1.1.27 Lactate dehydrogenase 1.1.1.29 Glycerate dehydrogenase 1.1.1.30 3-Hydroxybutyrate dehydrogenase 1.1.1.31 3-Hydroxyisobutyrate dehydrogenase 1.1.1.32 Mevaldate reductase 1.1.1.34 Hydroxymethylglutaryl-CoA reductase (NADPH) 1.1.1.35 3-Hydroxyacyl-CoA dehydrogenase 1.1.1.37 Malate dehydrogenase 1.1.1.39 Malate dehydrogenase (decarboxylating) 1.1.1.41 Isocitrate dehydrogenase (NAD+) 1.1.1.44 Phosphogluconate dehydrogenase (decarboxylating) 1.1.1.45 l-Gulonate dehydrogenase 1.1.1.49 Glucose-6-phosphate dehydrogenase 1.1.1.56 Ribitol dehydrogenase 1.1.1.79 Glyoxylate reductase (NADP+) 1.1.1.81 Hydroxypyruvate reductase 1.1.1.82 Malate dehydrogenase (NADP+) 1.1.1.85 3-Isopropylmalate dehydrogenase 1.1.1.86 Ketol-acid reductoisomerase 1.1.1.95 Phosphoglycerate dehydrogenase 1.1.1.100 3-Oxoacyl-[acyl-carrier-protein] reductase 1.1.1.102 3-Dehydrosphinganine reductase 1.1.1.105 Retinol dehydrogenase 1.1.1.130 3-Dehydro-L-gulonate 2-dehydrogenase 1.1.1.157 3-Hydroxybutyryl-CoA dehydrogenase 1.1.1.158 UDP-N-acetylmuramate dehydrogenase 1.1.1.169 2-Dehydropantoate 2-reductase 1.1.1.204 Xanthine dehydrogenase 1.1.1.205 IMP-dehydrogenase 1.1.3.8 l-Gulonolactone oxidase 1.1.3.22 Xanthine oxidase 1.1.99.1 Choline dehydrogenase 1.1.99.5 Glycerol-3-phosphate dehydrogenase 1.2.1.3 Aldehyde dehydrogenase (NAD+) 1.2.1.7 Benzaldehyde dehydrogenase (NADP+) 1.2.1.8 Betaine-aldehyde dehydrogenase 1.2.1.11 Aspartate-semialdehyde dehydrogenase 1.2.1.12 Glyceraldehyde-3-phosphate dehydrogenase 1.2.1.13 Glyceraldehyde-3-phosphate dehydrogenase 1.2.1.16 Succinate-semialdehyde dehydrogenase (NAD(P)+) 1.2.1.18 Malonate semialdehyde dehydrogenase (acetylating) 1.2.1.21 Glycolaldehyde dehydrogenase 1.2.1.23 2-Oxoaldehyde dehydrogenase (NAD+) 1.2.1.24 Succinate-semialdehyde dehydrogenase 1.2.1.25 2-Oxoisovalerate dehydrogenase (acylating) 1.2.1.27 Methylmalonate-semialdehyde dehydrogenase (acylating) 1.2.1.31 l-Aminoadipate-semialdehyde dehydrogenase 1.2.1.32 Aminomuconate-semialdehyde dehydrogenase 1.2.1.36 Retinal dehydrogenase 1.2.1.41 Glutamate-5-semialdehyde dehydrogenase 1.2.1.52 Oxoglutarate dehydrogenase 1.2.3.5 Glyoxylate oxidase 1.2.3.7 Indole-3-acetaldehyde oxidase 1.2.4.1 Pyruvate dehydrogenase (lipoamide) 1.2.4.2 Oxoglutarate dehydrogenase (lipoamide) 1.2.7.1 Pyruvate synthase 1.2.7.2 2-Oxobutyrate synthase 1.3.1.1 Dihydrouracil dehydrogenase (NAD+) 1.3.1.2 Dihydropyrimidine dehydrogenase (NADP+) 1.3.1.8 Acyl-CoA dehydrogenase (NADP+) 1.3.1.9 Enoyl-[acyl-carrier-protein] reductase (NADH) 1.3.1.10 Enoyl-[acyl-carrier-protein] reductase (NADPH, B-specific) 1.3.1.13 Prephenate dehydrogenase (NADP+) 1.3.1.14 Orotate reductase (NADH) 1.3.1.26 Dihydrodipicolinate reductase 1.3.1.35 Phosphatidylcholine desaturase 1.3.3.3 Coproporphyrinogen oxidase 1.3.3.4 Protoporphyrinogen oxidase 1.3.5.1 Succinate dehydrogenase (ubiquinone) 1.3.99.1 Succinate dehydrogenase 1.3.99.2 Butyryl-CoA dehydrogenase 1.3.99.3 Acyl-CoA dehydrogenase 1.3.99.7 Glutaryl-CoA dehydrogenase 1.3.99.10 Isovaleryl-CoA dehydrogenase 1.4.1.1 Alanine dehydrogenase 1.4.1.2 Glutamate dehydrogenase 1.4.1.7 Serine dehydrogenase 1.4.1.8 Valine dehydrogenase (NADP+) 1.4.1.9 Leucine dehydrogenase 1.4.1.10 Glycine dehydrogenase 1.4.1.14 Glutamate synthase (NADH) 1.4.1.19 Tryptophan dehydrogenase 1.4.3.1 d-Aspartate oxidase 1.4.3.2 l-Amino-acid oxidase 1.4.3.4 Amine oxidase (flavin-containing) 1.4.3.8 Ethanolamine oxidase 1.4.4.2 Glycine dehydrogenase (decarboxylating) 1.5.1.2 Pyrroline-5-carboxylate reductase 1.5.1.3 Dihydrofolate reductase 1.5.1.5 Methylenetetrahydrofolate reductase (NADP+) 1.5.1.6 Formyltetrahydrofolate dehydrogenase 1.5.1.7 Saccharopine dehydrogenase (NAD+, l-lysine-forming) 1.5.1.8 Saccharopine dehydrogenase (NADP+, l-lysine-forming) 1.5.1.9 Saccharopine dehydrogenase (NAD+, l-glutamate-forming) 1.5.1.10 Saccharopine dehydrogenase (NADP+, l-glutamate-forming) 1.5.1.12 1-Pyrroline-5-carboxylate dehydrogenase 1.5.3.1 Sarcosine oxidase 1.5.99.1 Sarcosine dehydrogenase 1.5.99.2 Dimethylglycine dehydrogenase 1.5.99.8 Proline dehydrogenase 1.6.4.1 Cystine reductase (NADH) 1.6.5.3 NADH dehydrogenase (ubiquinone) 1.6.6.1 Nitrate reductase (NADH) 1.6.6.2 Nitrate reductase [NAD(P)H] 1.6.6.3 Nitrate reductase (NADPH) 1.6.6.4 Nitrite reductase [NAD(P)H] 1.6.6.8 GMP reductase 1.7.3.3 Urate oxidase 1.7.7.1 Ferredoxin—nitrate reductase 1.7.99.4 Nitrate reductase 1.8.1.3 Hypotaurine dehydrogenase 1.8.1.4 Dihydrolipoamide dehydrogenase 1.8.2.1 Sulfite dehydrogenase 1.8.3.1 Sulfite oxidase 1.8.7.1 Sulfite reductase (ferredoxin) 1.8.99.1 Sulfite reductase 1.8.99.2 Adenylsulphate reductase 1.9.3.1 Cytochrome-c oxidase 1.10.2.1 l-Ascorbate—cytochrome-b5 reductase 1.10.2.2 Ubiquinol—cytochrome-c reductase 1.10.3.3 l-Ascorbate oxidase 1.10.99.1 Plastoquinol—plastocyanin reductase 1.13.11.1 Catechol 1,2-dioxygenase 1.13.11.2 Catechol 2,3-dioxygenase 1.13.11.5 Homogentisate 1,2-dioxygenase 1.13.11.6 3-Hydroxyanthranilate 3,4-dioxygenase 1.13.11.11 Tryptophan 2,3-dioxygenase 1.13.11.20 Cysteine dioxygenase 1.13.11.21 ß-Carotene 15,15´-dioxygenase 1.13.11.27 4-Hydroxyphenylpyruvate dioxygenase 1.13.11.34 Arachidonate 5-lipoxygenase 1.13.99.1 myo-lnositol oxygenase 1.14.11.1 g-Butyrobetaine dioxygenase 1.14.11.2 Procollagen-proline dioxygenase 1.14.11.8 Trimethyllysine dioxygenase 1.14.12.1 Anthranilate 1,2-dioxygenase (deaminating, decarboxylating) 1.14.13.5 Imidazoleacetate 4-monooxygenase 1.14.13.9 Kynurenine 3-monooxygenase 1.14.13.11 trans-Cinnamate 4-monooxygenase 1.14.13.12 Benzoate 4-monooxygenase 1.14.13.39 Nitric oxide synthase 1.14.16.1 Phenylalanine 4-monooxygenase 1.14.16.2 Tyrosine 3-monooxygenase 1.14.16.4 Tryptophan 5-monooxygenase 1.14.17.1 Dopamine ß-monooxygenase 1.14.18.1 Monophenol monooxygenase 1 14.99.1 Prostaglandin synthase 1 14.99.5 Stearoyl-CoA desaturase 1.14.99.7 Squalene monooxygenase 1.14.99.25 Linoleoyl-CoA desaturase 1.17.4.1 Ribonucleoside-diphosphate reductase 1.18.6.1 Nitrogenase TRANSFERASES 2.1.1.1 Nicotinamide N-methyltransferase 2.1.1.2 Guanidinoacetate N-methyltransferase 2.1.1.3 Thetin—homocysteine S-methyltransferase 2.1.1.4 Acetylserotonin N-methyltransferase 2.1.1.5 Betaine—homocysteine S-methyltransferase 2.1.1.6 Catechol O-methyl transferase 2.1.1.10 Homocysteine S-methyltransferase 2.1.1.13 5-Methyltetrahydrofolate—homocysteine S-methyl transferase 2.1.1.14 5-Methyltetrahydropteroyltriglutamate — homocysteine S-methyltransferase 2.1.1.17 Phosphatidylethanolamine N-methyltransferase 2.1.1.20 Glycine N-methyltransferase 2.1.1.28 Phenylethanolamine N-methyltransferase 2.1.1.45 Thymidylate synthase 2.1.1.71 Phosphatidyl-N-methylethanolamine N-methyltransferase 2.1.2.1 Glycine hydroxymethyltransferase 2.1.2.2 Phosphoribosylglycinamide formyltransferase 2.1.2.3 Phosphoribosylaminoimidazole carboxamide formyltransferase 2.1.2.5 Glutamate formiminotransferase 2.1.2.10 Aminomethyl transferase 2.1.3.1 Methylmalonyl-CoA carboxyltransferase 2.1.3.2 Aspartate carbamoyltransferase 2.1.3.3 Ornithine carbamoyltransferase 2.1.4.1 Glycine amidinotransferase 2.2.1.1 Transketolase 2.2.1.2 Transaldolase 2.3.1.1 Amino-acid N-acetyltransferase 2.3.1.4 Glucosamine-phosphate N-acetyltransferase 2.3.1.5 Arylamine N-acetyltransferase 2.3.1.6 Choline O-acetyltransferase 2.3.1.7 Carnitine O-acetyltransferase 2.3.1.8 Phosphate acetyltransferase 2.3.1.9 Acetyl-CoA C-acetyltransferase 2.3.1.12 Dihydrolipoamide S-acetyltransferase 2.3.1.15 Glycerol-3-phosphate O-acyltransferase 2.3.1.16 Acetyl-CoA C-acyltransferase 2.3.1.20 Diacylglycerol O-acyltransferase 2.3.1.23 Lysolecithin acyltransferase 2.3.1.24 Sphingosine N-acyltransferase 2.3.1.30 Serine O-acetyltransferase 2.3.1.37 5-Aminolevulinate synthase 2.3.1.38 [Acyl-carrier-protein] S-acetyltransferase 2.3.1.39 [Acyl-carrier-protein] S-malonytransferase 2.3.1.41 3-Oxoacyl-[acyl-carrier-protein] synthase 2.3.1.46 Homoserine O-succinyltransferase 2.3.1.50 Serine C-palmitoyltransferase 2.3.1.51 1-Acylglycerol-3-phosphate O-acyltransferase 2.3.1.76 Retinol O-fatty-acyltransferase 2.4.1.1 Phosphorylase 2.4.1.9 Inulosucrase 2 4.1.11 Glycogen (starch) synthase 2.4.1.13 Sucrose synthase 2.4.1.16 Chitin synthase 2.4.1.17 Glucuranosyltransferase 2.4.1.21 Starch synthase 2.4.1.22 Lactose synthase 2.4.1.23 Sphingosine ß-galactosyltransferase 2.4.1.29 Cellulose synthase (GDP-forming) 2.4.1.32 Glucomannan 4-ß-mannosyltransferase 2.4.1.33 Alginate synthase 2.4.1.47 Acylsphingosine galactosyltransferase 2.4.1.62 Ganglioside galactosyltransferase 2.4.1.68 Glycoprotein 6-a-l-fucosyltransferase 2.4.1.69 Galactoside 2-a-l-fucosyltransferase 2.4.2.1 Purine-nucleoside phosphorylase 2.4.2.2 Pyrimidine-nucleoside phosphorylase 2.4.2.4 Thymidine phosphorylase 2.4.2.8 Hypoxanthine phosphoribosyltransferase 2.4.2.9 Uracil phosphoribosyltransferase 2.4.2.10 Orotate phosphoribosyltransferase 2.4.2.11 Nicotinate phosphoribosyltransferase 2.4.2.14 Amidophosphoribosyltransferase 2.4.2.15 Guanosine phosphorylase 2.4.2.17 ATP phosphoribosyltransferase 2.4.2.18 Anthranilate phosphoribosyltransferase 2.4.2.19 Nicotinate-nucleotide pyrophosphorylase (carboxylating) 2.4.99.1-11 Sialyltransferases 2.4.99.7 Sialyltransferase 2.5.1.1 Dimethylallyltranstransferase 2.5.1.6 Methionine adenosyltransferase 2.5.1.10 Geranyltranstransferase 2.5.1.16 Spermidine synthase 2.5.1.19 3-Phosphoshikimate 1-carboxyvinyl-transferase 2.5.1.21 Farnesyltransferase 2.5.1.22 Spermine synthase 2.5.1.29 Farnesyltranstransferase 2.5.1.32 Geranylgeranyl-diphosphate geranylgeranyl transferase 2.6.1.- Transaminases 2.6.1.1 Aspartate transaminase 2.6 1.2 Alanine transaminase 2.6.1.4 Glycine transaminase 2.6 1.5 Tyrosine transaminase 2.6 1.6 Leucine transaminase 2.6.1.9 Histidinol-phosphate transaminase 2.6.1.13 Ornithine—oxo-acid transaminase 2.6.1.16 Glutamine—fructose-6-phosphate transaminase 2.6.1.17 Succinyldiaminopimelate transaminase 2.6.1.18 ß-Alanine—pyruvate transaminase 2.6.1.19 4-Aminobutyrate transaminase 2.6.1.22 l-3-Aminoisobutyrate transaminase 2.6.1.23 4-Hydroxyglutamate transaminase 2.6.1.27 Tryptophan transaminase 2.6.1.32 Valine—3-methyl-2-oxovalerate transaminase 2.6.1.36 l-Lysine 6-transaminase 2.6.1.39 2-Aminoadipate transaminase 2.6.1.42 Branched-chain-amino-acid transaminase 2.6.1.44 Alanine-glyoxylate transaminase 2.6.1.51 Serine—pyruvate transaminase 2.6.1.52 Phosphoserine transaminase 2.6.1.66 Valine—pyruvate transaminase 2.7.1.1 Hexokinase 2.7.1.2 Glucokinase 2.7.1.3 Ketohexokinase 2.7.1.4 Fructokinase 2.7.1.6 Galactokinase 2.7.1.7 Mannokinase 2.7.1.11 6-Phosphofructokinase 3 ATP Mito ch ondria l Intermembran e S pace NADPH+H + 1.2.1.13 1.2.4.1 2.3.1.12 1.8.1.4 Menaquinone 1.2.1.32 4.1.1.50 3 + NAD(P)

PEN NADPH M T P O I S P ES P - University of Wisconsin ... · PT O OH OH O OH ACNH H OO O HO OH OPU NHAC OH O HOH OH O OH N HCO HO O OPPG C H2 HO P UDP -N Ac Glucosamine pyruvate

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Page 1: PEN NADPH M T P O I S P ES P - University of Wisconsin ... · PT O OH OH O OH ACNH H OO O HO OH OPU NHAC OH O HOH OH O OH N HCO HO O OPPG C H2 HO P UDP -N Ac Glucosamine pyruvate

FMNFe--S FMNH2

2H+

MITOCHONDRIALMATRIX

2e -

4H+

3H+

CytoplasmCytoplasmic Membrane

4H+

2H+

1.6.5.3

NADH+H+

2H+

2H+

ADP Pi

I

2H+

Fe--SSUCCINATE

FUMARATEFAD1.3.5.1

Fe-S andCytochromes

1.10.2.2

2H+

2e -III

1.9.3.1Cu and

Cytochromes2H+

Cyt.c2H+

H O2

IV

ADP

3.6.1.3

Pi

3.6.1.34ATP

IIUQ

UQH2

MITO

CH

ON

DRIAL INNER MEMBRANE

2H+

Mito

cho

nd

rial O

ute

r Me

mb

rane

Mito

cho

nd

rial In

ner M

em

bra

ne

4.1.1.39

Fixation CO2

Ribulose-1:5-bis-P

H

OH OH

C C

H

CO CH O2 PPOCH2

P680 P7002H O2

H+

H+

H+

H+

2H+

H+

H+

H+

H+H+

H+

Thylakoid Lumen

H+

2H+

2e*2e*

+

Translocated protons

Mg+ +

2e*

O

O2

2

e-

Chloroplast Stroma

PC

-

Thylakoid Membrane

Mn

PHOTO-

Cyt.

ADP+Pi3.6.1.34Ferredoxin

b

f

Chloroplast Stroma

Membrane

ATP

3H+

2H+

2H+

PC

3.6.1.3

3H+

GlyceraldehydeHOCH CH(OH)CHO2

4.1.2.13

NADP

PQ

PQH2

SYSTEM IIPHOTO-

PheophytinChlorophyll

Thylakoid

To Brain -

AMINO ACIDS

PYRIMIDINES

PURINES

CATECHOLAMINES

AROMATIC AMINO ACIDS

STEROIDS

hvVISION

PORPHYRINS

STEROIDS

ISOPRENOIDS

PHOSPHOLIPIDS

LIPID

DEGRADATION

LIPID BIOSYNTHESIS

PHOTOSYNTHESIS

PENTOSES

HEXOSES

POLYSACCHARIDES

COCH CH(NH )COO2 3+

FOLICACID

C1POOL

VALINE

ATP

ATP

4.1.1.4 1.1.1.30

CH COCH3 3

CH COCH COO3 2

CH CH(OH)CH COO3 2

3-OH-ButyrateAcetone

Acetoacetate

KETONE BODIES

HYALURONIC ACID DERMATAN BLOOD GROUPSUBSTANCES

PEPTIDO-GLYCAN

N-Ac-Neuraminate(Sialate)

UDP-Iduronate

UDP-N-Ac-Galactosamine UDP-

Galacturonate

GDP-Fucose

TDP-Rhamnose

ADP-Glucose

UDP-Glucose

TDP-4-Oxo-6-deoxyglucose

MANNOSE

CHITIN CHONDROITIN PECTIN

ALGINATES

INULIN CELLULOSE

O-ANTIGENS STARCH GLYCOGEN

LACTOSE

GALACTOSE

O

OH

HO

OH

OH

CH3 O

OPPTO

OH

OH

O

OHACNH

HO OH

O

OHHO OPPU

NHAC

OH

OH OH

OH

HO

OH

NHCOCH

OH HO

O

OPPG

CH OH2

HO

P

UDP-N-Ac-Glucosamine

pyruvateN-Ac-Mannosamine-6-P UDP-Glucuronate

GDP-Mannose

N-Ac-Mannosamine UDP-N-Ac-Glucosamine N-Ac-Glucosamine-6-P

Sorbitol

Fructose-1-P

Erythrose-4-P

3-Dehydrogulonate

L-Xylose

L-Lyxose

D-Xylulose

D-Ribose

RibitolL-Arabitol L-Xylulose

L-Ribulose L-Ribulose-5-P

L-Xylulose-5-P

L-Arabinose Xylitol D-Xylose

D-Arabinose D-Ribulose

ASCORBATE

2, 3-Dioxogulonate

N-Ac-Glucosamine-1-P

Inositol-PInositolGlucuronateGulonate

Gulonolactone 2-Oxogulonolactone

Fructose

6-P-Gluconate

D-Ribulose-5-P

D-Xylulose-5-P

Mannose-1-P

GDP-Glucose

TDP-Glucose

UDP-Galactose

Galactose-P

Glucose-1-P

Glucose-6-P

Fructose-6-P

Fructose-1:6-bis-P

OH

H H HO

HOCH2 C C C C CO

OH OHH OH

H HO

HOCH2 C C C CO CO

OHH

H

OH H

C C

OH

CO

P-Ribosylamine

Glycerate2, 3-Diphospho-glycerate

3-P-Glyceraldehyde

1:3-bis-P-Glycerate

3-P-Glycerate

2-P-Glycerate

P-enolpyruvate

Inositol

CH OH2

CH OH2

HOCH

CH OH2

CH O2

HOCH

P

Glycerol

PYRUVATE

UDP-GalactoseUDP-Sugars

CH CH OH3 2

ETHANOL

Dihydroxy-acetone-P

(Glycerone-P)

Glucosamine-6-P

Phospho-serine

Chain elongation Mitochondrial

Serine

Serine

Indole-3-glycerol-P

3-Deoxy-D-arabino-heptulosonate-7-P

Indoleacetate(Auxin)

Indoxyl

Formylkynurenine Kynurenine 3-Hydroxykynurenine

3-Hydroxyanthranilate

2-Amino-3-carboxymuconate semialdehyde

NH

OH

Tryptamine 1-(o-Carboxy phenylamino)1-deoxyribulose-5-P

N-(5-P-Ribosyl)anthranilate

Anthranilate

Catechol

NH

Indole-acetaldehyde

NH

CH CHO2

Indolepyruvate

NH

C-CH(OH)CH(OH)CH O2 PCH

2-Aminomuconate-6-semialdehyde

CH CH NH2 2 2

NH

1.2.3.7

4.1.1.43

3.5.1.9 3.7.1.3

4.2.1.20

1.13.11.6 4.1.1.45

2.4.2.18

4.6.1.4

4.1.1.48

1.14.13.9

4.6.1.3 Dehydro-quinate

4.2.1.10 1.1.1.25 2.5.1.19Shikimate-3-P Shikimate-5enolpyruvate 3-P

ChorismatePEP

2.7.1.71

1.4.1.19

Homogentisate Phenylpyruvate

Cinnamate

Coumarate

Prephenate

2-Aminomuconate

Fumarate Aspartate

GLYCINE

Sarcosine

Hydroxy-pyruvate

P-Hydroxy-pyruvate

SERINE

Imidazoleglycerol-P

P-Ribosyl-ATP P-Ribosylformimino5-aminoimidazole-carboxamide-R P

Formiminoglutamate

Imidazolonepropionate

Urocanate

Cystathionine Homocysteine

Phosphoadenylyl-sulphate

(PAPS)

CH (NH )COO2 3+

Histidinol-PHistidinolHistidinal3.1.3.15 2.6.1.91.1.1.23

3.6.1.31

5.3.1.162.4.2.17

Asparagine

ALANINE

3-Sulphinylpyruvate

Oxobutyrate

2-Aceto-2-hydroxy-butyrate

O-Phospho-homoserine

HO SCH CH NH2 2 2 2

HypotaurineHO SCH CH NH3 2 2 2

Taurine

Glutamate

γ-Glutamylcysteine

Glutathione

Glycine

Cysteine

ß-Alanine

CysteateS-Adenosyl

homocysteine

4.2.99.2

1.1.1.864.2.1.9

1.1.1.86 4.2.1.92.6.1.32

4.1.3.18

2-Methylaceto-acetyl-CoA

2-Acetolactate 2-3-Dihydroxyisovalerate

2-Oxo-isovalerate

3-Hydroxy-isobutyrate

3-Hydroxy-Isobutyryl-CoA

Methylacrylyl-CoA

2-Methyl-3-hydroxy-

butyryl-CoA

Tiglyl-CoA 2 Methylbutyryl-CoA

2:3-Di-OH-3-methylvalerate

2-Oxo-3-methylvalerate

Isobutyryl-CoA

Cysteine

sulphinate

4.2.99.9

2-Isopropyl-malate

CH CH COCOO3 2

+CH CH(NH )COO3 3

CH CH(OH)COO3

HO SCH COCOO2 2

OCH COCOO2P

OCH CH(NH )COO2 3P

HOCH COCOO2

HOCH CH(NH )COO2 3+

+

OH

CH COCOO2

COO

OHOHO

COO

OHOH

HO P

COO

OHOH

O

CH2

P

COO

O-C-COOOH

OOH

OOC CH COCOO2

N H

HOC-CH(OH)CH(OH)CH 2OPCH

COO

NH2

COO

OHNH2COO

COO

OCH

OOCCH NHCH2 3

CH (CH ) COS-ACP3 2 14 CH (CH ) COSCoA3 2 14

CH (CH ) CH=CHCO-S-ACP3 2 2

CH CH=CHCO-S-ACP3 CH CH(OH)CH COS-ACP3 2

COSCoA

Linoleate

Oleoyl-CoA

Stearoyl-CoA Dehydrostearoyl-CoA OH-Stearoyl-CoA Oxostearoyl-CoA

Palmitoyl-ACP Palmitoyl-CoA

ACYL-ACP 2, 3-Enoyl-ACP

3, 4-Decenoyl-ACP

2, 3-Decenoyl-ACP

3-OH-Acyl-ACP 3-Oxoacyl-ACP

3-Oxo-Decanoyl-ACP

3-Oxo-Hexanoyl-ACP3-OH-Hexanoyl-ACP2, 3-Hexenoyl-ACP

Butanoyl-ACP Crotonoyl-ACP 3-OH-Butanoyl-ACP Acetoacetyl-ACP

Hexanoyl-ACP

3-OH-Decanoyl-ACPDecanoyl-ACP

Palmitoleoyl-ACP

γ-Linolenate Arachidonate Leukotriene B4

COSCoA

CO-S-ACP

Thromboxane B2

HOOCCH CO-S-ACP2

Malonyl-ACP

HOOCCH CO-SCoA2

Malonyl-Co-A

CH CO-S-ACP3Acetyl-ACP

CH O-CO-R2

CH OH2

R’-CO-OCH

FATTY ACID

ACYL-CoA(Cytosol)

CH O-CO-R2

CH O2

R’-CO-OCH

P

Cardiolipin Phosphatidylglycerol

AcetylcholineGlycerophosphocholine

Lysolecithin

Cholineplasmalogen

CDP-choline Choline-P

Mevaldate

CH (CH ) CH=CHCH(OH)CHCH OH3 2 12 2

Dehydrosphinganin Sphinganin 4-Sphingenin Psychosine

Acyl-CoAAcyl-CoA

CerebrosideGalactoseCH (CH ) CH=CHCH(OH)CHCH O-3 2 12 2

NHCOR

Isopentenyl-PP(C5)

Dimethylallyl-PP(C5)

Geranyl-geranyl-PP(C20)

Farnesyl-PP(C15)

Squalene(C30)

Geranyl-PP(C10)

Desmosterol Zymosterol Lanosterol

CH C = CHCH O3 2 PP

CH3

Ceramide

Gangliosides

NHCOR

CH O2 PP

OPPCH2

CHOLESTEROL

CH C(OH)CH CH OH3 2 2

CH COO2

CH C(OH)CH CHO3 2

CH COO2

NADP+Dehydroascorbate

OH

H O

HOCH2 C C C C CO

OHH OH

OH

H O

HOCH2 C C CO CO CO

H

NAD+Pi

ADP

Phytoene(C40)

Lycopene (C40)

ß-CAROTENE (C40)RhodopsinMetarhodopsin

Retinoate

trans-Retinal

11-cis-Retinoltrans-Retinol(Vitamin A)

Retinol esters

Dark

Light

Ubiquinone(Coenzyme Q)

Menaquinone

Plastoquinone

Phylloquinone(Vitamin K)

Opsin

CHO

CH OH2

CHO

CH OH2

CH3CH O3

CH O3 n

O

O

O

O

Phytol (C20)

α-Tocopherol(Vitamin E)

5-Aminolevulinate

PorphobilinogenUroporphyrinogenIII

CoproporphyrinogenIII

ProtoporphyrinogenIX

HEME

Quinolinate

Quinolinate-nucleotide

Nicotinate-nucleotide

Desamino-NAD

5-Hydroxy-tryptophan

5-Hydroxytryptamine(SEROTONIN)

N-Acetyl-5-O-methyl-serotonin(MELATONIN)

NH

CH CH NHCOCH2 2 3HO

NH

CH CH NHCOCH2 2 3CH O3

NICOTINATE

N-Acetyl-serotonin

2.4.2.19

Dopamine Dopa

Dopaquinone

THYROXINEMELANIN

OHOH

CHOHCH NHCH2 3

OHOH

CHOHCH NH2 2

4-OH-3-Methoxy-phenylglycol

CHOHCH NH2 2

OHOCH3OCH3

CHOHCH OH2

OH

OCH3

4-OH-3-Methoxy-D-mandelate

Cyclic AMPATP

Dephospho-Coenzyme A

4-P-Pantetheine

4-P-Pantothenylcysteine

4-P-Pantothenate

Pantoate

6.3.2.1

1.1.1.169

3.5.1.22

2.7.1.33

NH

NH

O

O

O

O

CH OH2

OHOCH3

CH(OH)COO

H2

NH3+

CH-COOCO

O

COO

NRibose- PN+

COO

NH

CH COO2

O

OH

CH O2 P

NHCOCH NH2 2

OHFormyl

glycinamide-R P

Urea

Formylglycinamidine-R P

Allantoate Allantoin URATE

ADP

Xanthine Hypoxanthine

Inosine

Adenine

Adenylo-succinate

5-Aminoimidazole-R P

5-Amino-4-imidazolecarboxylate-R P

5-Amino-4-imidazole(N-succinylcarboxamide)-R P

5-Aminoimidazolecarboxamide-R P

Formylamido-imidazole-

carboxamide-R P

H NCONH2 2

HNH C2 CHO

NHRP

NH

C

CCO

CCO

OCNH

NH

HN

HN

H

CCO

CCH

OCNH

N

N

HN

Carbamoylß-alanine

Dihydro-uracil Uracil

d-ADP

d-ATP

GTP GDP

XANTHOSINE-P(XMP)

TTP

TDP

ß-Ureidoisobutyrate

Dihydrothymine

Thymine d-UMP d-CMP d-CDP

CDP

Carbamoylaspartate

Dihydroorotate

Orotate Orotidine-P Uridine-P(UMP)

UDP

3-Amino-isobutyrate

CHCNH2

CHOCNH

NCHCO

CHOCN H

HN

CH-CH3CO

OCNH

HNCH2

CH2CH2

CO

OCNH

HN

CO

CHOCNH

HN C CH3

Methylmalonylsemialdehyde

OHCCHCOOCH3

CH2CO

CH-COOOCNH

HN CHCO

C-COOOCNH

HN

H NCONHCH CH COO2 2 2

CC

CCH

RPHC

NH

NH

OOC-CH-CH COO2

N

N

N

CHO

NHRP

NH

OC

H C2

2.7.7.433.1.3.29

1.1.1.158

5.1.3.132.7.1.383.2.1.23

3.1.3.294.1.3.20

2.7.1.60

5.1.3.14

5.1.3.7

5.1.3.1

2.7.1.4

5.4.2.3

3.1.1.17

1.1.1.49

2.7.1.1

1.1.1.21

2.7.7.23

3.1.3.251.13.99.11.1.1.19

1.1.3.8

5.3.1.3

2.7.1.53

1.1.1.9

2.7.1.15

2.7.1.17

5.1.3.4

5.1.3.1

2.2.1.2

4.1.2.13

2.7.1.11

2.7.1.47

2.2.1.1

1.2.1.12

1.1.1.29

1.1.1.95

1.3.1.35

1.14.99.25

2.3.1.41

2.3.1.41

2.3.1.41

1.1.1.100

5.3.99.5

4.2.1.60

5.3.99.31.14.99.1

1.13.11.34

1.3.1.101.3.1.9

1.14.99.5

1.3.1.9

4.2.1.61

4.2.1.60

4.2.1.60

4.2.1.59

4.2.1.58

1.3.1.9

1.3.1.9

6.2.1.3 3.1.2.20

1.1.1.100

5.3.1.1

HOOC-COOHOxalate

Glycolate

HOCH CHO2

Glycolaldehyde

Ethanolamine-P

2.7.1.30

2.3.1.7

3.1.3.4 2.7.1.107

3.7.1.2

4.1.3.5

2.7.8.8

2.1.1.172.1.1.71

1.3.1.35 2.7.8.2

3.1.4.3

3.1.4.4

2.7.7.15

3.1.1.5 3.1.4.2

2.7.1.32

2.7.1.82

2.6.1.21.4.1.1

4.1.1.1

2.3.1.50

1.1.1.102

3.1.4.12

2.7.8.3

2.4.1.62

3.2.1.46

5.2.1.31.2.1.36

2.3.1.763.1.1.21

5.2.1.7

5.4.99.71.14.99.7

4.3.1.84.2.1.75

4.1.1.371.3.3.31.3.3.44.99.1.1

2.5.1.29

2.4.1.47

4.1.1.28 2.3.1.5 2.1.1.4

6.3.5.16.3.1.5

2.4.2.11

2.7.7.18

2.6.1.51.13.11.5

2.1.1.28

2.1.2.2 6.3.3.1

3.5.2.5

1.4.1.10

1.7.3.3 1.1.1.204 1.1.3.221.1.3.22

4.1.1.28

4.1.1.21

2.1.2.3

2.4.2.1

1.5.99.2

2.1.1.5

2.6.1.22

3.5.2.3

2.6.1.511.4.1.7

3.1.3.3

2.6.1.52

2.1.3.2

ACETATE

2.4.2.4

2.1.1.45

RP

CHCO

CHOC N

HN

1.3.1.14 2.4.2.10 4.1.1.23

2.7.7.7

2.7.7.7

2.7.7.7

1.17.4.1

2.7.7.7

2.7.4.14

4.4.1.1

1.6.4.1

1.13.11.20

4.4.1.8

4.2.1.22

1.1.1.27

4.1.1.29 6.3.2.3

6.3.2.2

1.8.1.3

LACTATE

Acetaldehyde

2.7.1.24

2.7.7.3

4.1.1.36

Bile Acids

CH CH COSCoA3 2

Propanoyl-CoA

2.3.1.16

1.1.1.31

2.1.3.14.1.1.415.1.99.1

6.4.1.3

1.4.3.1

6.3.2.5

2.1.1.14

2.1.1.13

4.6.1.1

CDP-Ethanolamine

1.1.1.35 4.2.1.17

+HO SCH CH(NH )COO2 2 3

3.5.2.7NHHN

CH

OOC CHCH CH COO2 2

CMP-N-Acetylneuraminate

CDP-diacylglycerol

CHOLINE

Malonicsemi-

aldehyde

Ethanolamine

Glyoxylate

HISTAMINE

2.3.1.46Homoserine

Tyramine

Plant PigmentsTannins

Maleylacetoacetate

Fumarylacetoacetate

5.2.1.2

CH COO2

OH

OH

OH

CH CH NH2 2 2

OHOH

CH CH NH2 2 2

Hydroxyphenylpyruvate

α-Tocopherol(Vitamin E)

LIGNIN

d-GTP

OH

OH OH

O

HO

OH

P

OPPT

CH3HO

OHOH

O

NADPH

2.2.1.1

2.7.1.3

1.1.1.45

1.1.1.130

1.10.3.31.10.2.1

1.1.1.10

ATP

CH CH NH2 2 2

NH

HO

5.4.99.5

1.14.16.12.6.1.51.13.11.27

Indole

4.1.99.1

1.13.11.11

OHO

OH

NH C C CH CH O2 P

H HCOO

NH2

COO

6.3.5.3 6.3.2.6 4.3.2.2

GuanineDNA

6.3.4.44.3.2.2

CCO

CCH

HCNH

N

N

HN CCO

CCH

HCNH

N

N

HN

3.5.3.4

2.4.2.1

2.7.7.6 2.7.7.6

2.7.7.6

2.7.7.6

2.7.4.62.7.4.32.7.4.4

2.7.4.6

2.4.2.15

1.1.1.205

6.3.4.16.3.5.2

2.7.4.4

3.5.4.3

3.2.2.2

2.4.2.1

3.1.3.5

3.1.4.6

6.3.4.2

1.17.4.1

1.17.4.1

3.5.4.12

2.7.4.8

2.7.4.9

2.7.4.6

2.4.2.4

1.3.1.2

3.5.2.23.5.1.6

3.5.1.6 3.5.2.2 3.5.4.1

Diphospho-mevalonate

Mevalonate

3-Oxopentanoyl-CoA

3-Oxoacyl-CoA3-OH-Acyl-CoA2, 3-Enoyl-CoA

2, 3-Hexenoyl-CoA 3-OH-Hexanoyl-CoA

Acetoacetyl-CoA3-OH-Butanoyl-CoACrotonoyl-CoA

Pentanoyl-CoA Pentenoyl-CoA 3-OH-Pentanoyl-CoA

ACYL-CoA(Mitochondria)

1.1.1.35

1.1.1.35

1.1.1.157

1.3.99.3

1.3.99.3

1.3.99.2

1.1.1.35

Odd C Fatty acids

Succinylhomoserine

CO2

TRANSAMINATION

2-OXO ACID

Glutamyl-P

Glutamine

UREA

P-CreatineCreatine Creatinine

Glycine

CITRULLINE

Glutamic semialdehyde

2-AMINO ACID

Pyrroline-5-carboxylate

GlyoxylatePyruvate

4-Hydroxy-2-oxoglutarate

4-Hydroxy-glutamate

3-Hydroxy-pyrroline-

5-carboxylate

PutrescineH NCH CH CH CH NH2 2 2 2 2 2

Spermidine

Spermine

N -Trimethyllysine66N -Trimethyl-3-OH-lysine

Carnitine

Glutaryl-CoA Saccharopine2-Aminoadipatesemialdehyde

2-Aminoadipate2-Oxoadipate

Arginino-succinate

Guanidoacetate

Methylmalonyl-CoA

4.1.2.12

AspartylSemialdehyde

2, 3-Dihydro-dipicolinate

1.2.1.11

4.2.1.52 1.3.1.26 Piperideine-2, 6-dicarboxylate

N-Succinyl-2-amino-6-oxo-

pimelate

2.6.1.17N-Succinyl-2, 6diaminopimelate

Diamino-pimelate

3.5.1.18

3-Methyl-glutaconyl-CoA

(CH ) CHCH COSCoA3 2 2(CH ) CHCH COSCoA3 2 2

3-Methyl-crotonyl-CoA

Isovaleryl-CoA

OxopantoateHCHO

OOCCH C = CHCOSCoA2

CH3

CH COCHCOSCoA3

CH3

CH CH=CHCOSCoA3

CH3CH CH(OH)CHCOSCoA3

CH3

C(OH)CH(OH)COO

CH CH3 2

CH3

CH = CCOSCoA2

CH3

HOCH CHCOS-CoA-2

CH3

CH CHCO-SCoA3

CH3

C (OH)CH(OH)COOCH3

CH3

CH CH CHCOSCoA3 2

CH3

CH C = CHCOSCoA3

CH3

ATP

4-Aminobutyrate(GABA)

1.3.99.7

1.5.1.2

1.14.11.2

2.6.1.39 1.2.1.31

1.14.11.8

2.5.1.16

2.5.1.22

4.1.3.16

2.6.1.23

1.5.99.8

1.5.1.2

6.4.1.4 1.3.99.10

4.2.1.33

2.6.1.6

1.1.1.85Oxoleucine

COOH

(CH ) CHCHCH(OH)COO3 2

S-Adenosylmethylthiopropylamine

(Decarboxylated SAM)

PROLINE

Coenzyme A

CH C= CHCH3 2

CH3

OCH

CH

3

3HO

CH3CH3

CH3

CH C-CH H O3 2 2C PP

CH2

CH C= CHCH O2 2 PP

CH3

3-P-Glycerol

Phosphatidylethanolamine

CEPHALIN

3.1.4.12

2.7.8.3

Progesterone

1.5.1.12

2.7.3.2

4.3.1.1

4.2.1.173.1.2.4

2.6.1.32

4.4.1.15

Acetylserine 2.7.7.42.7.1.251.8.99.1Adenylylsulphate

(APS)

2.7.1.39

4.4.1.15

4.1.1.29

4.2.99.8

2.3.1.30

P-Ribosyl-PP

1.1.1.1

1.2.1.4

Aspartyl-P

2.7.2.4

5.1.1.7

2.7.1.40

4.1.3.18

4.1.3.18

5.1.99.1

5.4.99.2

4.1.1.71

1.5.1.9

1.14.11.1

CHOLINE

2.1.1.13

1.3.1.2

NHCH CH SH2 2 NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2P

ADP- NHCH CH SH2 2 NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2

P-ADP- NHCH CH SH2 2 NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2

1.4.1.8

1.3.99.3

1.3.99.3

1.4.1.9

4.2.1.18

4.1.1.20

1.3.99.7

1.8.99.2

+CH CO-OCH CH(NH )COO2 2 3

2.5.1.6

2.1.1.10

2.1.1.20

1.1.1.3

1.1.1.3

4.2.1.18

1.2.1.16

4.1.1.12

4.1.2.5

4.3.1.5

4.2.1.20

2.1.2.1

2.1.

1.20

Glyoxylate

2.1.1.6

1.4.3.4

1.14.18.1

1.14.16.2

Hexanoyl-CoA

Butanoyl-CoA

1.18.6.1

1.4.1.2

3.5.1.2

6.3.4.16

6.3.5.5

2.7.2.11

2.1.3.3

NO1.14.13.39

3.5.3.63.5.3.1

4.3.2.1

4.1.1.17

2.7.7.41

2.6.1.4

1.1.1.100

1.1.1.8

2.3.1.512.3.1.15

2.7.8.5

SO -42

1.14.16.4

NH2 OOC OOC

4.1.1.25

1.3.1.13

1.3.1.13

2.7.4.6

CYTIDINE-triphosphate

(CTP)

Cytosine

2.4.2.9

4.1.1.11

2.6.1.18

4.3.1.3

4.2.1.49

3HSO-

1.1.1.105

2.3.1.41

NADPH

1.1.1.22

2.3.1.4

5.5.1.4

3.2.1.26 3.2.1.48

2.6.1.16

1.1.1.14

2.7.7.34

4.2.1.47

2.4.1.682.4.1.69

2.4.1.9

5.3.1.8

2.4.1.11

O

OPPU

CH OH2

CH OH2

HO OH

OH

HO

2.4.1.21

OXALOACETATE

4.2.1.52

ATP

GTPGDP+Pi

1.2.1.18

CITRATE

MALATE

SUCCINYL-CoA

ISOCITRATE

4.2.1.18

4.2.1.3

1.3.5.1

4.2.1.2

1.1.1.37

6.2.1.43.1.2.3

1.7.99.41.6.6.1

5-Aminolevulinate

1.6.6.4

Glycine

O

CHC

CHOCN

HN

DP

CHCO

CHOCN

HN

RPPP

OCH2

H

C C

H

OHOH

CH

NHNCH

CP

H

O

OCH2 C C

H

OH

H

OH

C

H

C CCNH2

CCH

HCN

RP(PP)

N

N

N+

P

NH2H

O

OCH2 C C

H

OH

H

OH

C

H

C COC

CCH

HCN

RP

N

N

NHP

H

OCH2 C C

H

OHOH

CO CH2 C

CONH2

CCH

HCN

RP

N

N

NHP

+OOCCH N(CH )2 3 3

Betaine

Betainealdehyde

2.4.1.16

5.1.3.6

2.4.1.33

2.7.7.13

5.4.2.8

5.3.1.8

O

OH

CH OH2

HO

O PHO

2.7.1.28

2.7.1.31

6.3.4.13

5.3.1.1

2.2.1.1

4.1.1.9

3.1.2.11

ß-OH-ß-Methyl-glutaryl-CoA

2.3.1.37

1.4.1.146.3.1.23.5.1.2

6.3.4.5

5.3.1.6

2.5.1.21

2.1.1.2

3.5.2.10

6.3.2.136.3.2.7-10

2.7.7.27

2.7.7.9

3.5.4.10

CCO

CCH

OCN RP

N

NH

HN

CCO

CCH

N

N

N

HN

RPH N2 C

2.7.4.6

1.17.4.1

2.7.4.6

2.6.1.13

SUCCINATE

Carbamoyl-P

2.3.1.9

Carnitine

2.6.1.44

2.6.1.4

CH C(OH)CH COSCoA3 2

CH COO2

1.2.3.5

1.1.1.34

2.3.1.16

4.1.3.5

2.3.1.16

4.1.3.4

Glyoxylate

4.1.3.1

HOOCCHO

4.1.3.2

4.1.1.15

2.6.1.19

2.6.1.1

4.2.1.16

Carnosine

CH CH NH2 2 2C

NHNC

HC

H

4.1.1.22

4.3.1.3

Ubiquinone

Plastoquinone

D-Ribose-5-P

CH CH(NH )COO2 3HO+

O

OH

OH

HO

OPPU

COO-

O

OH

OH

HO OPPU

COO-

OH

H OH

HOCH2 C C CO

H

CO COO-

OCHOHCHOHAcNH

HO

OPC

OCO -CH OH2

OCHOHCHOHAcNH

HO

OH

COOCH OH2

O

OHOHHOHO

CH O2 P

O

OHACNH

HO OH

CH O2 P

O

OOHHOHO P

CH OH2

O

OHOH HOHO

CH OH2

O

OHHO OH

3

CH O2 PO

OHHO O

NHCOCH3

P

CH OH2CH OH2CH OH2

O

OHHO OH

NH2

CH O2 P

O

OH

HO

OH

OPPU

CH OH2

O

O

HO

OH

OH

HO

P

CH OH2

CH OH2O

OHO

OH

OH

O

OHOH

OH

CH OH2

O

OHHO

OH

OH

CH2CH OP2

OH

H H HOH

C C C C

OH OHH

COO-HOCH2

H

OH OHOH

C C C CHO

HH

H

OH OHH

C C C CHO

HOHOH

H OHH

C C C CHO

HOH

H

OH HOH

C C C CHO

OHH

HOCH2

OH

H HOH

C C C CHO

OHH

HOCH2

OH

H OHOH

C C C CHO

HH

H

OH HOH

C C C C

OHH H

OH

COO-POCH2

OH

H OH

C C CO

H

POCH2 CH OH2

H

OH H

C C CO

OH

CH OH2

CH OH2POCH2

H

OH OH

C C CO

H

CH OH2POCH2

OH

H H

C C CO

OH

CH OH2POCH2

H

OH OH

C C CO

H

CH OH2

OH

H OH

C C CO

H

CH OH2

OH

H H

C C CO

OH

CH OH2

H

OH OHH

C C C

HOH

CH OH2

OH

H OHOH

C C C

HH

CH OH2

H

OH HOH

C C C C

OHH H

OH

CH OH2HOCH2

H

OH OH

C C CHO

H

POCH2

H

OH HOH

C C C CO

OHH

CH O2 P

H

OH OHOH

C C C

HH

HOCH2 CH OH2

H

OH OH

C C C

H

CO

H

HO

POCH2 CH OH2

P

H

OH OH

C C C

H

CO

H

HO

CH O2 POCH2

H

OH OH

C C

H

C CHO

OH

H

POCH2POCH2

O

OH

NH2

OH

CH O2 P

CHOHCHOPOCH2

COHOCH2 CH O2 P

O

OH

O OP P

OH

CH O2 P

CHOHCOOPPOCH2

CHOHPOCH2 COO

COO

OH

OHOOH

COO

CH (CH ) CH(OH)CH COS-CoA3 2 14 2CH (CH ) CH(OH)CH COS3 2 14 2

CH (CH ) COCH COS-CoA3 2 14 2

CH (CH ) COCH COS-CoA3 2 14 2

CH (CH ) COS-CoA3 2 n+2

CH (CH ) CH=CHCOS-CoA3 2 14

CH (CH )3 2 nCH=CHCOS-CoA

CH (CH )3 2 5 2CH=CHCH COSACP

CH (CH )3 2 6CH=CHCOSACP

CH (CH )3 2 6COCH COSACP2CH (CH )3 2 6 2 2CH CH COSACP

CH (CH )3 2 2 2 2CH CH COSACP

CH CH CH COSACP3 2 2

CH (CH )3 2 6CH(OH)CH COSACP2

CH CH=CHCO.S-ACP3

CH (CH )3 2 2 2COCH COSACP

CH3COCH COSACP2

CH (CH )3 2 n 2COCH COSACPCH (CH )3 2 n 2CH(OH)CH COSACP

CH (CH )3 2 2 2CH(OH)CH COSACP

CH (CH ) CH CH COSCoA3 2 2 2n CH (CH ) CH=CHCOSCoA3 2 n CH (CH CH(OH)CH COSCoA3 2n

CH (CH ) CH CH COSCoA3 2 2 2 2 CH (CH ) CH=CHCOSCoA3 2 2

CH (CH ) COCH COSCoA3 2 2n

CH COCH COSCoA3 2

CH (CH ) CH(OH)CH COSCoA3 2 2 2

CH CH(OH)CH COSCoA3 2CH CH=CHCOSCoA3CH CH CH COSCoA3 2 2

CH CH CH CH COSCoA3 2 2 2 CH CH CH=CHCOSCoA3 2 CH CH CH(OH)CH COSCoA3 2 2

CH (CH ) COCH COSCoA3 2 2 2

CH CH COCH COSCoA3 2 2

OH OH

HO OH

O

O-CH O-PO2

CH CHOHCH OH2 2

O

CH2

CH2

OR'-CO-OCH

CH O-CO-R2

CH O-PO2

O-

HOCH CH2 2NH3+POCH CH2 2NH3

+CPP- OCH CH2 2NH3

+

O

-

CH O-CO-R2

CH O P2 OCH CH2 2NH3+

CH COCH CH N(CH )3 2 2 3 3

HOCH CH N(CH )2 2 3 3

+

CH CH 2 COO(NH )3+

OHOH

CH CH 2 COO- (NH )3+

CO

NH2

CH CH(NH )COO2 3+

NHOC

CO

NHOC

NH

CH

H N2

HCCH

N

N

C

RPH N2

CHC

CHOCN

N

DP

NH2

RPPP

CHC

CHOCN

N

NH2

CC

CCH

RP(P)HC

N

N

N

N

NH2

H NCOO2 P

(CH ) NH2 3 2H N(CH ) NH2 2 3 (CH ) NH2 4

(CH ) NH2 3 2H N(CH ) NH2 2 4

CH -SCH CH CHNH3 2 2 2

Adenosyl

+

+CH3

CH3

CHCH(NH )COO3

++C

NHNC

HC

H

CH CH(NH )CH OH2 3 2

+C

NHNC

HC

H

CH CH(NH )CH OP2 3 2C

NHNCH

HC CH COCH OP2 2

+HSCH CH CH(NH )COO2 2 3

+

+SCH CH CH(NH )COO2 2 3

CH CH(NH )COO2 3

RP

CO

C-COOOCN

HN CH

2.4.1.23

CH (CH ) CH=CHCH(OH)CHCH OH3 2 12 2CH (CH ) CH=CHCH(OH)CHCH OH3 2 12 2

NH3+

CH (CH ) CH(OH)CHCH OH3 2 14 2

NH3+

CH (CH ) COCHCH OH3 2 14 2

NH3+

GalactoseCH (CH ) CH=CHCH(OH)CHCH O-3 2 12 2CH (CH ) CH=CHCH(OH)CHCH O-3 2 12 2

NH3+NH3+

4.1.1.70

H NCONH2 2

NH4+

OHCCH N(CH )2 3 3

+

C-CH3CO

CHOCN DP

HN

DP

CPP-OCH CH N(CH )2 2 3 3

+OCH CH N(CH )P 2 2 3 3

+

GTP

2-OXOGLUTARATE

1.2.1.41

4.1.3.8

FUMARATE

UDP-N-Ac-Muramate

O

O

CH CH3

COO-

NHAC

HO OPPU

CH OH2

4.1.3.20

O

OH

CH3

HO HO OPPG

2.7.7.24

2.4.1.22

2.7.7.12

5.1.3.2

5.3.1.4

Sedoheptulose-PP

3.1.1.28

4.2.1.24

N

CH2

CH2

N

N

N

CH3

CH3

CH

CH

COO

CH2CH

CH2

H C3

HC

C

C

H

H

Fe

CH2

CH2

COO- -

CH3

CH3

CH2

CH2

CH2

H C3

H C3N

H

NH

NH

NH

CH

CH

H C2

C

CH2

H2

-

CH2

CH2

COO

CH2

CH2

COO -

H C2

H C2

CH2

CH2

OOC

COO

H N2

NH

-

-

OOCCH CH COCH NH2 2 2 2-

CH2

H C2

H C2

H C2

H2

H2

CH2

CH2 CH2

CH2

CH2

CH2

NH

NH

NH

NH

COO

COO

COOCOO

C

C

-

-

CH2

CH2

COO

CH2

CH2

COO- -

-

-

OOC-

OOC-

CH3

CH3

H C3

H C3

H C2

H2

H2

NH

NH

NH

NH

CH2

CH2

CH2

CH2

CH2

C

C

COO-

CH2

CH2

COO

CH2

CH2

COO- -

COO-

COO-

OOCCOCH CH2 2COO--

1.2.4.2

OOCCH CH COSCoA2 2-

1.1.1.41

OOCCH CH COO2 2

OOCCH=CHCOO

OOCCH(OH)CH COO2

CH COO2

CHCOO

CHOHCOO

C(OH)COO

CH COO2

CH COO2

CH C(OH)CH CH O3 2 2 PP

CH COO2

OHCCOO

HOCH COO2

NH2

H NCNHCH COO2 2

+ NH2

H NCN(CH )CH COO2 3 2

+ NH2

HNCN(CH )CH COO3 2P-

+ HN CNH CO

N CH2

CH3

OOCCHCH COO2

H NCNHCH CH CH CH2 2 2 2

N(NH )3

+COO

CHCOOHC

CH2HOCH

N

OOCCH(OH)CH CH(NH )COO2 3

+

CHCOO

CH2HOCH

H C2NH

NH

CHCOO

CH2CH2

CH2

OOCCH(OH)CH COCOO2

N

CHCOO

CH2CH2

CH

CH COCOO3 OHCCOO

+H NCONHCH CH CH CH2 2 2 2 (NH )3 COO

H NOCCH CH CH2 2 2 COO(NH )3

+

R-CO-COO

+

COOR-CH(NH )3+

COOH NOCCH CH2 2 (NH )3+

OOC-CH-COSCoA

CH3

P OOCCH CH2 COO(NH )3+

OOCCH CH CHO2 2

OHCCH CH2 COO(NH )3

+

(CH ) NCH CH(OH)CH COO3 3 2 2

+

OHCCH CH CH2 2

+COO(NH )3

POOCCH CH CH2 2

+COO(NH )3

OHCCH CH CH CH2 2 2 COO(NH )3+

NH CHCH CH COO2 2

COO

CH CH CH CH CH2 2 2 2 COO(NH )3

+

(CH ) N(CH )3 3 2 3CH CH(NH )COO2 3+ +

CH2CH

OOCCN

HCCH-COO

CH2CH2

CH-COO OOCCN

H C2

OOCCOCH CH CH CH-COO2 2 2CH CH2 2 2

OOCCH CH CONH2 2 OOCCHCH CH CH CH-COO2 2 2

OOCCH CH CONH2 2CH2 2

NH3+

OOCCH-CH CH CH CHCOO2 2 2

NH3+

NH3+

4.1.1.32

(CH ) CHC(OH)CH3 2 2

COOH

COO (CH ) CHCH COCOO3 2 2

HOCH CHCOO2

CH3

CHCOCOOCH3CH COC(OH)CH3 3

COO

+POCH CH CH(NH )COO2 2 3

+HOCH CH CH(NH )COO2 2 3

+CH CH CH(NH )COO2 2 3 OOCCH CH2COO 2

+CH SH2

OOCCH(NH )CH CH CONHCHCONHCH COO3 2 2 2

HOCH C(CH ) COCOO2 3 2

HOCH C(CH ) CH(OH)COO2 3 2

NHCH CH COO2 2HOCH C(CH ) CH(OH)CO3 2)2 3 2

NHCH CH COO2 2OCH C(CH ) CH(OH)CO2 3 2P

CH CH3 2

CH3

CH+

CH(NH )COO3

CH COC(OH)CH CH3 2 3

COO CHCOCOO

CH CH3 2

CH3

NHCHCH SH2

COO NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2P

+CH SH2

OOCCH(NH )CH CH CONHCHCOO3 2 2

+AdenosylSCH CH CH(NH )COO2 2 3

+SCH CH CH(NH )COO2 2 3

+HO SCH CH(NH )COO3 2 3

+

S-CH CH(NH )COO2 3

S-CH CH(NH )COO2 3+

HSCH CH(NH )COO2 3

1.1.1.23

H

C

NHNC

HC CH CHCOO2

NHCOCH CH NH2 2 2+

H

C

NHNC

HC CH CH(NH )COO2 3

CHCH CH COO2 2

NHNCH

OC C CH CHCOO

NHNCH

CH

CH COO3

NH

OOC

CH-COOOCNH2 CH2

H NCH CH COO2 2 2

H NCH2 2

CH3CHCOO H NCONHCH CHCOO2 2

CH3

CCO

CH

RPHC N

N

N

HN

C

CCO

CHHCO

N

N

N RP

CCH

N

NH N2

HC

CCO

CH

N

NC

CCH

N

N

RP

H N2

H N2C

O

O

O P~ ~P O

O

O O

P O

O

CH2

N

N

N

N

O

OHOH

NH2

HCCHN

N

N

N O

O

P O O

O

CH2

OH

NH2

HCCH

COOCO

NHOC

NH

CH

H N2NH2

OOC-CH-CH COO2

HNCO CCH

N

N

C

RPRPH N2

OOCC

CH

NRP

N

CH N2

CH=CHCOO

OH

CH=CHCOO

CH COCOO2

CH2

P

COO

OHO

O

O

COO

O

CH COO2OCH COO2-OOC

OCH2 CH2

OHHC

P

HOCH HCOH

OCCOO

COOHO

OHOHO

NH2COOOCH

NH

CH COCOO2NH

CHO

CO

NH2OH

CH CH(NH )COO2 3

+

COO

COO

N+

COO

COORP

O

OH

OH

HO OPPU

COO

O

OH

NHCOCH3

HO

OPPU

COOCH OH2

O

OCCH2 NHAC

HO OPPU

COO

CH OH2

O

OHHO OH

OH

COO

OOCCH N(CH )2 3 2

Dimethylglycine

1.1.99.1

1.2.1.8

COOHO HO

COOCOO

O

HO OH

COO

CH(O ) PPOCH2 COO CH(OH)HOCH2 COOCOO

CH(O )PHOCH2 COO

CH =C(O )2 P COO

CH CO3 COO

4.1.3.7

OOCCOCH COO2

CONH2

Ribose -O - P - O - P - O- Adenosine(P)+N

O

O

O

O

+

COO

NRibose - O - P - O - P - O -Adenosine

O

O

O

O

II

IIOH

O

CH CH 2 COO(NH )3+

Epinephrine(Adrenaline)

Norepinephrine(Noradrenaline)

Normetepinephrine(Normetadrenaline)

HOCH CH N(CH )2 2 3 3

+

Adenosyl+

+SCH CH CH(NH )COO2 2 3

(CH ) N(CH )3 3 2 3CH CH(NH )COO2 3+ +

OH

OOCCH CH CH COSCoA2 2 2

OOCCH CH CH NH2 2 2 2

OOCCH CH CH COCOO2 2 2 OOCCH CH CH CH2 2 2 COOCOO(NH )3

++

HOH

HOH

HHO

HHO

H

Prostaglandin PGE 2

OH

HOCH2 C C CO C COO

OHH

OHH H

-

COO

OR'-CO-OCH

CH O-CO-R2

CH O POCMP2

O

CH CH N(CH )2 2 3+

OHOCH

CH OPO2

CH OH2

O-

CH OPO2

O

CH OCH=CHR2

CH CH N(CH )2 2 3 3+

O-CH OPO2

OR'-CO-OCH

CH O-CO-R23.1.1.32

CH CH N(CH )2 2 3 3+

O-

OHOCH

CH OPO2

CH O-CO-R2

CH CH N(CH )2 2 3 3

+

O-

CH CH(NH )COO2 3+

+C

NHNC

HC

H

CH CH(NH )CHO2 3

HS

11-cis-Retinal

Pi

ADP

ATP

NADP+

GDP-Mannuronate

Mannose-6-PDehydro-shikimate

Shikimate

RNA

d-GDP

d-CTP

GUANOSINE-P(GMP)

ß-Alanine

P-Ribosyl-AMP P-Ribulosylformimino5-aminoimidazole-carboxamide-R P

Imidazoleacetol-P

HS HSO-

PANTOTHENATE

3-Isopropyl-malate

Succinicsemialdehyde

N2

NO3

_

NO2

_

CO2

2.4.1.17

Diacylglycerol

ACETYL-CoACH COSCoA3

2.3.1.6

1.1.1.39

1.14.12.1

1.4.4.2

CH CHO3

3.5.4.19

4.2.1.19

3.3.1.1

4.1.1.12

4.1.2.5

OHCCH COO2

6.3.5.4

2.1.4.1

2.4.99.7

5.1.3.12

1.1.1.132

4.2.1.46

2.7.1.7

2.4.1.29

2.4.1.21

2.4.1.13

2.4.1.1etc.

5.4.2.2

2.7.1.6

2.7.7.10

3.1.1.18

4.1.1.34

2.7.1.47

2.7.1.16

3.1.3.9

ADP

P-Gluconolactone

1.1.1.44

O

OOHHO

OH

CH O2 P

PHENYLALANINETYROSINE

TRYPTOPHAN

INOSINE-P(IMP)

THYMIDINE-P

HISTIDINE

URIDINE-triphosphate

(UTP)

CYSTINE CYSTEINE

ISOLEUCINE

LEUCINE

LYSINE

ASPARTATE

ORNITHINE

ARGININEHYDROXYPROLINE

PHOSPHATIDYLSERINE Phosphatidyl

inositol

LECITHIN

SPHINGOMYELIN

STEROIDS

Pregnenolone

CHLOROPHYLL

HEMOGLOBIN

2.7.6.1

2.4.2.146.3.4.7

5.3.1.9

3.1.3.11

2.7.2.3

H

OH OH

C C C

H

CO

OH

C

H

H

OH

POCH2 CH O2 P

5.4.2.1

ADP

4.2.1.11

Endoplasmic Reticulum

1.1.1.100

3.1.1.3

Phosphatidate

2.3.1.39

4.2.1.17

4.2.1.17

4.2.1.55

1.1.1.79

1.2.1.21

1.4.3.8

1.1.1.32

2.7.1.362.7.4.2

4.1.1.33

2.5.1.1

2.5.1.10

2.7.8.5

2.7.8.1

4.1.1.65

2.7.7.14

1.3.99.7

PO

O

CH (CH ) CH=CHCH(OH)CHCH O3 2 12 2

NHAcyl

CH CH N(CH )2 2 3 3+

O-

3.5.1.23

1.13.11.21

2.5.1.32

1.1.1.105

2.4.2.19

1.2.1.32

METHIONINE

4.1.3.27

4.2.1.51

1.14.17.1

1.14.18.1

1.14.13.11

Glycinamide-ribosyl-P

4.2.1.22

3-Oxohexanoyl-CoA

THREONINE

1.2.1.25

1.2.1.25

1.2.1.25

1.5.1.7 - 10

GLUTAMATE

1.7.7.1

2.3.1.38

ATP

NADH

SUCROSE

ADENOSINE-P(AMP)

TriacylglycerolFAT

RNA

CH2

OC-COOOH

COO

CH CH 2 COO(NH )3+

TR

AN

SLO

CATE

D PROTONS

3H+1H+

1H+

GLYCOPROTEINSGANGLIOSIDES

MUCINS

2.7.1.2

4.1.2.-

2.6.1.-

Some other pathways occurring in the mitochondria �are identified by a pale yellow background

Small numbers refer to the IUBMB Enzyme Commission �Reference Numbers for Enzymes

L E G E N D

Pentose Phosphate Pathway

CarbohydratesBiosynthesis Degradation

Amino AcidsBiosynthesis Degradation

LipidsBiosynthesis Degradation

Purines & PyrimidinesBiosynthesis Degradation

Vitamins, Co-Enzymes & Hormones

Photosynthesis Dark Reactions

Human Metabolism is identified as far as possible by black arrowsBiosynthesis Degradation

GLUCOSE

O-Acyl-carnitine

O-Acyl-carnitine

+NAD

OH

O-

-

R'-CO-OCH

R'-CO-OCH

O HCO-CO-R

CH CH(OH)CH O-P-OCH2 2 2

CH O-CO-R’2

OR'-CO-OCH

O-

CH O-CO-R2

CH O-PO2O-

2.7.8.11

H NCH CH CH CH2 2 2 2 COO(NH )3

+

2.3.1.20

NH2

+

+H NCNHCH CH CH CH2 2 2 2 COO(NH )3

H

OH HOH

C C C CO

OHH

CH OH2

R-CH2COO

CH O-CO-R2

CH O-CO-R"2

R’-CO-OCH

OH

O

CH CHNH2 3+

OR'-CO-OCH

CH O-CO-R2

CH O PO2

COO

OOCCH CH CH2 2 COO(NH )3

+ OOCCH CH(NH )COO2 3

+CH CH(OH)CH(NH )COO3 3

O

OHHO

OH

OH

CH OH2CH OH2

NH

CH O-CO-R2

COMPARTMENTATIONThe "BACKBONE" of metabolism involves GLYCOLYSIS, the TCA CYCLE and OXIDATIVE PHOSPHORYLATION. It is a major source of energy (ATP) and is the origin and termination of most of the pathways. GLYCOLYSIS occurs in the CYTOPLASM. The TCA CYCLE is in the MITOCHONDRIAL MATRIX. OXIDATIVE PHOSPHORYLATION (ATP SYNTHESIS) spans the MITOCHONDRIAL INNER MEMBRANE. This last part has been redesigned to illustrate the activation of ATP-synthase and formation of ATP - driven by the electromotive translocation of protons across the mitochondrial inner membrane. A similar compartmentation occurs in the chloroplast, where light-driven proton translocation across the inner thylakoid membrane initiates synthesis of the ATP necessary for Photosynthesis. In both cases flow of electrons and protons is shown in red or blue arrows

Electron Flow Proton Flow

HOCH2

HOCH2

HOCH2

HOCH2

HOCH2

HOCH2

HOCH2

HOCH2

HOCH2 HOCH2

HOCH2 HOCH2

SYSTEM I

NH

(H N)(CH )42 CH(NH )COO3CH(NH3+++

CH3

H

N

1.3.1.13

+

CH -3

CH -3

+(CH ) CHCH3 2 2 CH(NH )COO3

H C3H C3

R'-CO-OCH

O-

4.1.1.28

2.7.1.15 Ribokinase2.7.1.16 Ribulokinase2.7.1.17 Xylulokinase2.7.1.19 Phosphoribulokinase2.7.1.24 Dephospho-CoA kinase2.7.1.25 Adenylylsulfate kinase2.7.1.28 Triokinase2.7.1.30 Glycerol kinase2.7.1.31 Glycerate kinase2.7.1.32 Choline kinase2.7.1.33 Pantothenate kinase2.7.1.34 Pantetheine kinase2.7.1.36 Mevalonate kinase2.7.1.39 Homoserine kinase2.7.1.40 Pyruvate kinase2.7 1.47 D-Ribulokinase2.7.1.53 l-Xylulokinase2.7.1.60 N-Acylmannosamine kinase2.7.1.71 Shikimate kinase2.7.1.80 Pyrophosphate—serine phosphotransferase2.7.1.82 Ethanolamine kinase2.7.1.107 Diacylglycerol kinase2.7.2.3 Phosphoglycerate kinase2.7.2.4 Aspartate kinase2.7.2.6 Formate kinase2.7.2.11 Glutamate 5-kinase2.7.3.2 Creatine kinase2.7.4.2 Phosphomevalonate kinase2.7.4.3 Adenylate kinase2.7.4.4 Nucleoside-phosphate kinase2.7.4.6 Nucleoside-diphosphate kinase2.7.4.8 Guanylate kinase2.7.4.9 dtmp kinase2.7.4.14 Cytidylate kinase2.7.6.1 Ribose-phosphate pyrophosphokinase2.7.7.3 Pantetheine-phosphate adenylyltransferase2.7.7.4 Sulfate adenylyl transferase2.7.7.6 RNA nucleotidyltransferase (DNA-directed)2.7.7.7 DNA nucleotidyltransferase (DNA-directed)2.7.7.9 UTP—glucose-1-phosphate uridylyltransferase2.7.7.10 UTP—hexose-1-phosphate uridylyltransferase2.7.7.12 UDP glucose—hexose-1-phosphate uridylyltransferase2.7.7.13 Mannose-1-phosphate guanylyltransferase2.7.7.14 Ethanolamine-phosphate cytidylyltransferase2.7.7.15 Choline-phosphate cytidylyltransferase2.7.7.18 Nicotinate-nucleotide adenylyltransferase2.7.7.23 UDP-N-acetylglucosamine pyrophosphorylase2.7.7.24 Glucose-1-phosphate thymidylyltransferase2.7.7.27 Glucose-1-phosphate adenylyltransferase2.7.7.34 Glucose-1-phosphate guanylyltransferase2.7.7.41 Phosphatidate cytidylyltransferase2.7.7.43 N-Acylneuraminate cytidylyltransferase2.7.8.1 Ethanolamine phosphotransferase2.7.8.2 Diacylglycerol cholinephosphotransferase2.7.8.3 Ceramide cholinephosphotransferase2.7.8.5 CDPdiacylglycerol—glycerol-3- phosphate 3-phosphatidyltransferase2.7.8.8 CDPdiacylglycerol—serine O-phosphatidyltransferase2.7.8.11 CDPdiacylglycerol—inositol 3-phosphatidyltransferase2.8.3.5 3-Oxoacid CoA-transferase2.8.3.6 3-Oxoadipate CoA-transferase

HYDROLASES3.1.1.3 Triacylglycerol lipase3.1.1.4 Phospholipase A23.1.1.5 Lysophospholipase3.1.1.7 Acetylcholinesterase3.1.1.17 Gluconolactonase3.1.1.21 Retinyl-palmitate esterase3.1.1.28 Acylcarnitine hydrolase3.1.1.31 6-Phosphogluconolactonase3.1.1.32 Phospholipase A13.1.2.1 Acetyl-CoA hydrolase3.1.2.3 Succinyl-CoA hydrolase3.1.2.4 3-Hydroxyisobutyryl-CoA hydrolase3.1.2.11 Acetoacetyl-CoA hydrolase3.1.2.20 Acyl-CoA hydrolase3.1.3.2 Acid phosphatase3.1.3.3 Phosphoserine phosphatase3.1.3.4 Phosphatidate phosphatase3.1.3.5 5´-Nucleotidase3.1.3.9 Glucose-6-phosphatase3.1.3.11 Fructose-bisphosphatase3.1.3.15 Histidinol-phosphatase3.1.3.25 myo-Inositol-1(or 4)-monophosphatase3.1.3.27 Phosphatidylglycerophosphatase3.1.3.29 N-Acylneuraminate-9-phosphatase3.1.3.31 Nucleotidase3.1.4.2 Glycerophosphocholine phosphodiesterase3.1.4.3 Phospholipase C3.1.4.4 Phospholipase D3.1.4.10 1-Phosphatidylinositol phosphodieterase3.1.4.12 Sphingomyelin phosphodiesterase3.2.1.21 ß-Glucosidase3.2.1.23 ß-Galactosidase3.2.1.26 ß-Fructofuranosidase3.2.1.45 Glucosylceramidase3.2.1.46 Galactosylceramidase3.2.1.48 Sucrose a-glucosidase3.2.2.2 Inosine nucleosidase3.3.1.1 Adenosylhomocysteinase3.5.1.1 Asparaginase3.5.1.2 Glutaminase3.5.1.6 ß-Ureidopropionase3.5.1.9 Arylformamidase3.5.1.18 Succinyl-diaminopimelate desuccinylase3.5.1.22 Pantothenase3.5.1.23 Ceramidase3.5.2.2 Dihydropyrimidinase3.5.2.3 Dihydroorotase3.5.2.5 Allantoinase3.5.2.7 Imidazolonepropionase3.5.2.10 Creatininase3.5.3.1 Arginase3.5.3.4 Allantoicase3.5.3.6 Arginine deiminase3.5.4.1 Cytosine deaminase3.5.4.3 Guanine deaminase3.5.4.6 AMP deaminase3.5.4.10 IMP cyclohydrolase3.5.4.12 dCMP deaminase3.5.4.19 Phosphoribosyl-AMP cyclohydrolase3.6.1.3 Adenosinetriphosphatase3.6.1.15 Nucleoside-triphosphatase3.6.1.31 Phosphoribosyl-ATP pyrophosphatase3.6.1.34 H+-transporting ATP synthase3.7.1.2 Fumarylacetoacetase3.7.1.3 Kynureninase3.9.1.1 Phosphoamidase

LYSASES4.1.1.1 Pyruvate decarboxylase4.1.1.3 Oxaloacetate decarboxylase4.1.1.4 Acetoacetate decarboxylase4.1.1.9 Malonyl-CoA decarboxylase4.1.1.11 Aspartate 1-decarboxylase4.1.1.12 Aspartate 4-decarboxylase4.1.1.15 Glutamate decarboxylase4.1.1.17 Ornithine decarboxylase4.1.1.20 Diaminopimelate decarboxylase4 1.1.21 Phosphoribosylaminoimidazole carboxylase4.1.1.22 Histidine decarboxylase4.1.1.23 Orotidine-5’-phosphate decarboxylase4.1.1.25 Tyrosine decarboxylase4.1.1.28 Aromatic-L-amino-acid decarboxylase4.1.1.29 Sulfoalanine decarboxylase4.1.1.32 Phosphoenolpyruvate carboxykinase (GTP)4.1.1.33 Diphosphomevalonate decarboxylase4.1.1.34 Dehydro-l-gulonate decarboxylase4.1.1.36 Phosphopantothenoylcysteine decarboxylase4.1.1.37 Uroporphyrinogen decarboxylase4.1.1.39 Ribulose-bisphosphate carboxylase4.1.1.41 Methylmalonyl-CoA decarboxylase4.1.1.43 Phenylpyruvate decarboxylase4.1.1.45 Aminocarboxymuconate- semialdehyde decarboxylase4.1.1.48 Indole-3-glycerol-phosphate synthase4.1.1.49 Phosphoenolpyruvate carboxykinase (ATP)4.1.1.50 Adenosylmethionine decarboxylase4.1.1.65 Phosphatidylserine decarboxylase4.1.1.71 2-Oxoglutarate decarboxylase4.1.2.5 Threonine aldolase4.1.2.12 Ketopantoaldolase4.1.2.13 Fructose-bisphosphate aldolase4.1.2.14 2-Dehydro-3-deoxyphosphogluconate aldolase4.1.3.1 Isocitrate lyase4.1.3.2 Malate synthase4.1.3.4 Hydroxymethylglutaryl-CoA lyase4.1.3.5 Hydroxymethylglutaryl-CoA synthase4.1.3.7 Citrate (si)-synthase4.1.3.8 ATP citrate (pro-S)-lyase4.1.3.16 4-Hydroxy-2-oxoglutarate aldolase4.1.3.18 Acetolactate synthase4.1.3.20 N-Acylneuraminate-9-phosphate synthase4.1.3.21 Homocitrate synthase4.1.3.22 Citramalate lyase4.1.3.27 Anthranilate synthase4.1.99.1 Tryptophanase4.2.1.2 Fumarate hydratase4.2.1.3 Aconitate hydratase4.2.1.4 Citrate dehydratase4.2.1.9 Dihydroxy-acid dehydratase4.2.1.10 3-Dehydroxyquinate dehydratase4.2.1.11 Phosphopyruvate hydratase (enolase)4.2.1.13 l-Serine dehydratase4.2.1.16 Threonine dehydratase4.2.1.17 Enoyl-CoA hydratase4.2.1.18 Methylglutaconyl-CoA hydratase4.2.1.19 Imidazoleglycerol-phosphate dehydratase4.2.1.20 Tryptophan synthase4.2.1.22 Cystathionine B-synthase4.2.1.24 Porphobilinogen synthase4.2.1.33 3-Isopropylmalate dehydratase4.2 1.46 dTDPglucose 4,6-dehydratase4.2.1.47 GDPmannose 4,6-dehydratase4.2.1.49 Urocanate hydratase4.2.1.51 Prephenate dehydratase4.2.1.52 Dihydrodipicolinate synthase4.2.1.55 3-Hydroxybutyryl-CoA dehydratase4.2.1.58 Crotonoyl-[acyl-carrier-protein] hydratase4.2.1.59 3-Hydroxyoctanoyl-[acyl-carrier protein] dehydratase4.2.1.60 3-Hydroxydecanoyl-[acyl-carrier protein] dehydratase4.2.1.61 3-Hydroxypalmitoyl-[acyl-carrier protein] dehydratase4.2.1.75 Uroporphyrinogen-III synthase4.2.1.80 2-Oxopent-4-enoate hydratase4.2.99.2 Threonine synthase4.2.99.8 Cysteine synthase4.2.99.9 O-Succinylhomoserine (thiol)-lyase4.3.1.1 Aspartate ammonia-lyase4.3.1.2 Methylaspartate ammonia-lyase4.3.1.3 Histidine ammonia-lyase4.3.1.5 Phenylalanine ammonia-lyase4.3.2.1 Argininosuccinate lyase4.3.2.2 Adenylosuccinate lyase4.4.1.1 Cystathionine g-lyase4.4.1.8 Cystathionine ß-lyase4.4.1.15 D-Cysteine desulfhydrase4.6.1.1 Adenylate cyclase4.6.1.3 3-Dehydroquinate synthase4.6.1.4 Chorismate synthase4.99.1.1 Ferrochelatase

ISOMERASES5.1.3.1 Ribulose-phosphate 3-epimerase5.1.3.2 UDPglucose 4-epimerase5.1.3.4 l-Ribulose-phosphate 4-epimerase5.1.3.6 UDPglucuronate 4-epimerase5.1.3.7 UDP-N-acetylglucosamine 4-epimerase5.1.3.12 UDPglucuronate 5´-epimerase5 1.3.13 dTDP-4-Dehydrorhamnose 3,5-epimerase5.1.3.14 UDP-N-acetylglucosamine 2-epimerase5.1.99.1 Methylmalonyl-CoA epimerase5.2.1.2 Maleylacetoacetate isomerase5.2.1.3 Retinal isomerase5.2.1.7 Retinol isomerase5.3.1.1 Triose-phosphate isomerase5.3.1.3 Arabinose isomerase5.3.1.4 l-Arabinose isomerase5.3.1.5 Xylose isomerase5.3.1.6 Ribose-5-phosphate isomerase5.3.1.8 Mannose-6-phosphate isomerase5.3.1.9 Glucose-6-phosphate isomerase5.3.1.16 N-(5´-Phospho-d-ribosylformimino)- 5-amino-1-(5´´-phosphoribosyl)- 4-imidazolecarboxamide isomerase5.3.3.2 Isopentenyl-diphosphate ³-isomerase5.3.99.3 Prostaglandin-E synthase5.3.99.5 Thromboxane-A synthase5.4.2.1 Phosphoglycerate mutase5.4.2.2 Phosphoglucomutase5.4.2.3 Phosphoacetylglucosamine mutase5.4.2.8 Phosphomannomutase5.4.3.8 Glutamate-1-semialdehyde 2,1-aminomutase5.4.99.2 Methylmalonyl-CoA mutase5.4.99.5 Chorismate mutase5.4 99.7 Lanosterol synthase5.5.1.4 myo-Inositol- l-phosphate synthase

LIGASES6.2.1.3 Long-chain-fatty-acid-CoA ligase6.3.1.1 Aspartate—ammonia ligase6.3.1.2 Glutamate—ammonia ligase6.3.1.4 Aspartate—ammonia ligase (ADP-forming)6.3.1.5 NAD+ synthetase6.3.2.1 Pantoate—ß-alannine ligase6.3.2.2 Glutamate—cysteine ligase6.3.2.3 Glutathione synthase6.3.2.5 Phosphopantothenate—cysteine ligase6.3.2.6 Phosphoribosylaminoimidazole- succinocarboxamide synthase6.3.2.7 UDP-N-Acetylmuramoyl-l-alanyl- d-glutamate—lysine ligase6.3.2.8 UDP-N-acetylmuramate—alanine ligase6.3.2.9 UDP-N-acetylmuramoylalanine— d-glutamate ligase6.3.2.10 UDP-N-acetylmuramoylalanyl- d-glutamyl-lysine—d-alanyl-d-alanine ligase6.3.2.13 UDP-N-Acetyl muramoylalanyl-d- glutamate—2,6-diaminopimelate ligase6.3.3.1 Phosphoribosylglycinamidine cyclo-ligase6.3.4.1 GMP synthase6.3.4.2 CTP synthase6.3.4.3 Formate—tetrahydrofolate ligase6.3.4.4 Adenylosuccinate synthase6.3.4.5 Argininosuccinate synthase6.3.4.7 Ribose-5-phosphate—ammonia ligase6.3.4.13 Phosphoribosylamine—glycine ligase6.3.4.16 Carbamoyl-phosphate synthase (ammonia)6.3.4.17 Formate—dihydrofolate ligase6.3.5.1 NAD+ synthetase (glutamine-hydrolysing)6.3.5.2 GMP synthetase (glutamine-hydrolysing)6.3.5.3 Phosphoribosylformylglycinamidine synthetase6.3.5.4 Asparagine synthase (glutamine-hydrolysing)6.3.5.5 Carbamoyl-phosphate synthase (glutamine-hydrolysing)6.4.1.1 Pyruvate carboxylase6.4.1.2 Acetyl-CoA carboxylase6.4.1.3 Propionyl-CoA carboxylase6.4.1.4 Methylcrotonoyl-CoA carboxylase

OXIDOREDUCTASES1.1.1.1 Alcohol dehydrogenase1.1.1.3 Homoserine dehydrogenase1.1.1.8 Glycerol-3-phosphate dehydrogenase1.1.1.9 D-Xylulose reductase1.1.1.10 l-Xylulose reductase1.1.1.14 l-Iditol dehydrogenase1.1.1.19 Glucuronate reductase1.1.1.21 Aldehyde reductase1.1.1.22 UDPglucose dehydrogenase1.1.1.23 Histidinol dehydrogenase1.1.1.25 Shikimate dehydrogenase1.1.1.27 Lactate dehydrogenase1.1.1.29 Glycerate dehydrogenase1.1.1.30 3-Hydroxybutyrate dehydrogenase1.1.1.31 3-Hydroxyisobutyrate dehydrogenase1.1.1.32 Mevaldate reductase1.1.1.34 Hydroxymethylglutaryl-CoA reductase (NADPH)1.1.1.35 3-Hydroxyacyl-CoA dehydrogenase1.1.1.37 Malate dehydrogenase1.1.1.39 Malate dehydrogenase (decarboxylating)1.1.1.41 Isocitrate dehydrogenase (NAD+)1.1.1.44 Phosphogluconate dehydrogenase (decarboxylating)1.1.1.45 l-Gulonate dehydrogenase1.1.1.49 Glucose-6-phosphate dehydrogenase1.1.1.56 Ribitol dehydrogenase1.1.1.79 Glyoxylate reductase (NADP+)1.1.1.81 Hydroxypyruvate reductase1.1.1.82 Malate dehydrogenase (NADP+)1.1.1.85 3-Isopropylmalate dehydrogenase1.1.1.86 Ketol-acid reductoisomerase1.1.1.95 Phosphoglycerate dehydrogenase1.1.1.100 3-Oxoacyl-[acyl-carrier-protein] reductase1.1.1.102 3-Dehydrosphinganine reductase1.1.1.105 Retinol dehydrogenase1.1.1.130 3-Dehydro-L-gulonate 2-dehydrogenase1.1.1.157 3-Hydroxybutyryl-CoA dehydrogenase1.1.1.158 UDP-N-acetylmuramate dehydrogenase1.1.1.169 2-Dehydropantoate 2-reductase1.1.1.204 Xanthine dehydrogenase1.1.1.205 IMP-dehydrogenase1.1.3.8 l-Gulonolactone oxidase1.1.3.22 Xanthine oxidase1.1.99.1 Choline dehydrogenase1.1.99.5 Glycerol-3-phosphate dehydrogenase1.2.1.3 Aldehyde dehydrogenase (NAD+)1.2.1.7 Benzaldehyde dehydrogenase (NADP+)1.2.1.8 Betaine-aldehyde dehydrogenase1.2.1.11 Aspartate-semialdehyde dehydrogenase1.2.1.12 Glyceraldehyde-3-phosphate dehydrogenase1.2.1.13 Glyceraldehyde-3-phosphate dehydrogenase1.2.1.16 Succinate-semialdehyde dehydrogenase (NAD(P)+)1.2.1.18 Malonate semialdehyde dehydrogenase (acetylating)1.2.1.21 Glycolaldehyde dehydrogenase1.2.1.23 2-Oxoaldehyde dehydrogenase (NAD+)1.2.1.24 Succinate-semialdehyde dehydrogenase1.2.1.25 2-Oxoisovalerate dehydrogenase (acylating)1.2.1.27 Methylmalonate-semialdehyde dehydrogenase (acylating)1.2.1.31 l-Aminoadipate-semialdehyde dehydrogenase1.2.1.32 Aminomuconate-semialdehyde dehydrogenase1.2.1.36 Retinal dehydrogenase1.2.1.41 Glutamate-5-semialdehyde dehydrogenase1.2.1.52 Oxoglutarate dehydrogenase1.2.3.5 Glyoxylate oxidase1.2.3.7 Indole-3-acetaldehyde oxidase1.2.4.1 Pyruvate dehydrogenase (lipoamide)1.2.4.2 Oxoglutarate dehydrogenase (lipoamide)1.2.7.1 Pyruvate synthase1.2.7.2 2-Oxobutyrate synthase1.3.1.1 Dihydrouracil dehydrogenase (NAD+)1.3.1.2 Dihydropyrimidine dehydrogenase (NADP+)1.3.1.8 Acyl-CoA dehydrogenase (NADP+)1.3.1.9 Enoyl-[acyl-carrier-protein] reductase (NADH)1.3.1.10 Enoyl-[acyl-carrier-protein] reductase (NADPH, B-specific)1.3.1.13 Prephenate dehydrogenase (NADP+)1.3.1.14 Orotate reductase (NADH)1.3.1.26 Dihydrodipicolinate reductase1.3.1.35 Phosphatidylcholine desaturase1.3.3.3 Coproporphyrinogen oxidase1.3.3.4 Protoporphyrinogen oxidase1.3.5.1 Succinate dehydrogenase (ubiquinone)1.3.99.1 Succinate dehydrogenase1.3.99.2 Butyryl-CoA dehydrogenase1.3.99.3 Acyl-CoA dehydrogenase1.3.99.7 Glutaryl-CoA dehydrogenase1.3.99.10 Isovaleryl-CoA dehydrogenase1.4.1.1 Alanine dehydrogenase1.4.1.2 Glutamate dehydrogenase1.4.1.7 Serine dehydrogenase1.4.1.8 Valine dehydrogenase (NADP+)1.4.1.9 Leucine dehydrogenase1.4.1.10 Glycine dehydrogenase1.4.1.14 Glutamate synthase (NADH)1.4.1.19 Tryptophan dehydrogenase1.4.3.1 d-Aspartate oxidase1.4.3.2 l-Amino-acid oxidase1.4.3.4 Amine oxidase (flavin-containing)1.4.3.8 Ethanolamine oxidase1.4.4.2 Glycine dehydrogenase (decarboxylating)1.5.1.2 Pyrroline-5-carboxylate reductase1.5.1.3 Dihydrofolate reductase1.5.1.5 Methylenetetrahydrofolate reductase (NADP+)1.5.1.6 Formyltetrahydrofolate dehydrogenase1.5.1.7 Saccharopine dehydrogenase (NAD+, l-lysine-forming)1.5.1.8 Saccharopine dehydrogenase (NADP+, l-lysine-forming)1.5.1.9 Saccharopine dehydrogenase (NAD+, l-glutamate-forming)1.5.1.10 Saccharopine dehydrogenase (NADP+, l-glutamate-forming)1.5.1.12 1-Pyrroline-5-carboxylate dehydrogenase1.5.3.1 Sarcosine oxidase1.5.99.1 Sarcosine dehydrogenase1.5.99.2 Dimethylglycine dehydrogenase1.5.99.8 Proline dehydrogenase1.6.4.1 Cystine reductase (NADH)1.6.5.3 NADH dehydrogenase (ubiquinone)1.6.6.1 Nitrate reductase (NADH)1.6.6.2 Nitrate reductase [NAD(P)H]1.6.6.3 Nitrate reductase (NADPH)1.6.6.4 Nitrite reductase [NAD(P)H]1.6.6.8 GMP reductase1.7.3.3 Urate oxidase1.7.7.1 Ferredoxin—nitrate reductase1.7.99.4 Nitrate reductase1.8.1.3 Hypotaurine dehydrogenase1.8.1.4 Dihydrolipoamide dehydrogenase1.8.2.1 Sulfite dehydrogenase1.8.3.1 Sulfite oxidase1.8.7.1 Sulfite reductase (ferredoxin)1.8.99.1 Sulfite reductase1.8.99.2 Adenylsulphate reductase1.9.3.1 Cytochrome-c oxidase1.10.2.1 l-Ascorbate—cytochrome-b5 reductase1.10.2.2 Ubiquinol—cytochrome-c reductase1.10.3.3 l-Ascorbate oxidase1.10.99.1 Plastoquinol—plastocyanin reductase1.13.11.1 Catechol 1,2-dioxygenase1.13.11.2 Catechol 2,3-dioxygenase1.13.11.5 Homogentisate 1,2-dioxygenase1.13.11.6 3-Hydroxyanthranilate 3,4-dioxygenase1.13.11.11 Tryptophan 2,3-dioxygenase1.13.11.20 Cysteine dioxygenase1.13.11.21 ß-Carotene 15,15´-dioxygenase1.13.11.27 4-Hydroxyphenylpyruvate dioxygenase1.13.11.34 Arachidonate 5-lipoxygenase1.13.99.1 myo-lnositol oxygenase1.14.11.1 g-Butyrobetaine dioxygenase1.14.11.2 Procollagen-proline dioxygenase1.14.11.8 Trimethyllysine dioxygenase1.14.12.1 Anthranilate 1,2-dioxygenase (deaminating, decarboxylating)1.14.13.5 Imidazoleacetate 4-monooxygenase1.14.13.9 Kynurenine 3-monooxygenase1.14.13.11 trans-Cinnamate 4-monooxygenase1.14.13.12 Benzoate 4-monooxygenase1.14.13.39 Nitric oxide synthase1.14.16.1 Phenylalanine 4-monooxygenase1.14.16.2 Tyrosine 3-monooxygenase1.14.16.4 Tryptophan 5-monooxygenase1.14.17.1 Dopamine ß-monooxygenase1.14.18.1 Monophenol monooxygenase1 14.99.1 Prostaglandin synthase1 14.99.5 Stearoyl-CoA desaturase1.14.99.7 Squalene monooxygenase1.14.99.25 Linoleoyl-CoA desaturase1.17.4.1 Ribonucleoside-diphosphate reductase1.18.6.1 Nitrogenase

TRANSFERASES2.1.1.1 Nicotinamide N-methyltransferase2.1.1.2 Guanidinoacetate N-methyltransferase2.1.1.3 Thetin—homocysteine S-methyltransferase2.1.1.4 Acetylserotonin N-methyltransferase2.1.1.5 Betaine—homocysteine S-methyltransferase2.1.1.6 Catechol O-methyl transferase2.1.1.10 Homocysteine S-methyltransferase2.1.1.13 5-Methyltetrahydrofolate—homocysteine S-methyl transferase2.1.1.14 5-Methyltetrahydropteroyltriglutamate — homocysteine S-methyltransferase2.1.1.17 Phosphatidylethanolamine N-methyltransferase2.1.1.20 Glycine N-methyltransferase2.1.1.28 Phenylethanolamine N-methyltransferase2.1.1.45 Thymidylate synthase2.1.1.71 Phosphatidyl-N-methylethanolamine N-methyltransferase2.1.2.1 Glycine hydroxymethyltransferase2.1.2.2 Phosphoribosylglycinamide formyltransferase2.1.2.3 Phosphoribosylaminoimidazole carboxamide formyltransferase2.1.2.5 Glutamate formiminotransferase2.1.2.10 Aminomethyl transferase2.1.3.1 Methylmalonyl-CoA carboxyltransferase2.1.3.2 Aspartate carbamoyltransferase2.1.3.3 Ornithine carbamoyltransferase2.1.4.1 Glycine amidinotransferase2.2.1.1 Transketolase2.2.1.2 Transaldolase2.3.1.1 Amino-acid N-acetyltransferase2.3.1.4 Glucosamine-phosphate N-acetyltransferase2.3.1.5 Arylamine N-acetyltransferase2.3.1.6 Choline O-acetyltransferase2.3.1.7 Carnitine O-acetyltransferase2.3.1.8 Phosphate acetyltransferase2.3.1.9 Acetyl-CoA C-acetyltransferase2.3.1.12 Dihydrolipoamide S-acetyltransferase2.3.1.15 Glycerol-3-phosphate O-acyltransferase2.3.1.16 Acetyl-CoA C-acyltransferase2.3.1.20 Diacylglycerol O-acyltransferase2.3.1.23 Lysolecithin acyltransferase2.3.1.24 Sphingosine N-acyltransferase2.3.1.30 Serine O-acetyltransferase2.3.1.37 5-Aminolevulinate synthase2.3.1.38 [Acyl-carrier-protein] S-acetyltransferase2.3.1.39 [Acyl-carrier-protein] S-malonytransferase2.3.1.41 3-Oxoacyl-[acyl-carrier-protein] synthase2.3.1.46 Homoserine O-succinyltransferase2.3.1.50 Serine C-palmitoyltransferase2.3.1.51 1-Acylglycerol-3-phosphate O-acyltransferase2.3.1.76 Retinol O-fatty-acyltransferase2.4.1.1 Phosphorylase2.4.1.9 Inulosucrase2 4.1.11 Glycogen (starch) synthase2.4.1.13 Sucrose synthase2.4.1.16 Chitin synthase2.4.1.17 Glucuranosyltransferase2.4.1.21 Starch synthase2.4.1.22 Lactose synthase2.4.1.23 Sphingosine ß-galactosyltransferase2.4.1.29 Cellulose synthase (GDP-forming)2.4.1.32 Glucomannan 4-ß-mannosyltransferase2.4.1.33 Alginate synthase2.4.1.47 Acylsphingosine galactosyltransferase2.4.1.62 Ganglioside galactosyltransferase2.4.1.68 Glycoprotein 6-a-l-fucosyltransferase2.4.1.69 Galactoside 2-a-l-fucosyltransferase2.4.2.1 Purine-nucleoside phosphorylase2.4.2.2 Pyrimidine-nucleoside phosphorylase2.4.2.4 Thymidine phosphorylase2.4.2.8 Hypoxanthine phosphoribosyltransferase2.4.2.9 Uracil phosphoribosyltransferase2.4.2.10 Orotate phosphoribosyltransferase2.4.2.11 Nicotinate phosphoribosyltransferase2.4.2.14 Amidophosphoribosyltransferase2.4.2.15 Guanosine phosphorylase2.4.2.17 ATP phosphoribosyltransferase2.4.2.18 Anthranilate phosphoribosyltransferase2.4.2.19 Nicotinate-nucleotide pyrophosphorylase (carboxylating)2.4.99.1-11 Sialyltransferases2.4.99.7 Sialyltransferase2.5.1.1 Dimethylallyltranstransferase2.5.1.6 Methionine adenosyltransferase2.5.1.10 Geranyltranstransferase2.5.1.16 Spermidine synthase2.5.1.19 3-Phosphoshikimate 1-carboxyvinyl-transferase2.5.1.21 Farnesyltransferase2.5.1.22 Spermine synthase2.5.1.29 Farnesyltranstransferase2.5.1.32 Geranylgeranyl-diphosphate geranylgeranyl transferase2.6.1.- Transaminases2.6.1.1 Aspartate transaminase2.6 1.2 Alanine transaminase2.6.1.4 Glycine transaminase2.6 1.5 Tyrosine transaminase2.6 1.6 Leucine transaminase2.6.1.9 Histidinol-phosphate transaminase2.6.1.13 Ornithine—oxo-acid transaminase2.6.1.16 Glutamine—fructose-6-phosphate transaminase2.6.1.17 Succinyldiaminopimelate transaminase2.6.1.18 ß-Alanine—pyruvate transaminase2.6.1.19 4-Aminobutyrate transaminase2.6.1.22 l-3-Aminoisobutyrate transaminase2.6.1.23 4-Hydroxyglutamate transaminase2.6.1.27 Tryptophan transaminase2.6.1.32 Valine—3-methyl-2-oxovalerate transaminase2.6.1.36 l-Lysine 6-transaminase2.6.1.39 2-Aminoadipate transaminase2.6.1.42 Branched-chain-amino-acid transaminase2.6.1.44 Alanine-glyoxylate transaminase2.6.1.51 Serine—pyruvate transaminase2.6.1.52 Phosphoserine transaminase2.6.1.66 Valine—pyruvate transaminase2.7.1.1 Hexokinase2.7.1.2 Glucokinase2.7.1.3 Ketohexokinase2.7.1.4 Fructokinase2.7.1.6 Galactokinase2.7.1.7 Mannokinase2.7.1.11 6-Phosphofructokinase

3

ATP

Mito

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term

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Sp

ace

NADPH+H+

1.2.1.13

1.2.4.12.3.1.121.8.1.4

Menaquinone

1.2.1.32

4.1.1.50

3

+NAD(P)

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Enzymes available from Sigma
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Enzymes available from Sigma
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Enzymes available from Sigma
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Enzymes available from Sigma
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Enzymes available from Sigma
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Enzymes available from Sigma
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