Metabolic Pathways Poster (3 MB)

1
2H + H+ OXALOACETATE PYRUVATE SUCCINYL-CoA GLUTARATE CITRATE MALATE 2-OXO- ASPARTATE NO 2 - NO 3 - N 2 NH 4 CH3COSCoA ACETYL-CoA HOH CO2 NAD T R A N S A M I N A T I O N 2H + 2H + + CO2 5-Amino- levulinate Glycine H+ H+ H+ H+ H+ H+ c H+ H+ a F0 F1 F1 β 2 1 α β α γ 10 c-sub-u n it s A D P + P i a H+ 3.6.1.3 4 H + -tra n s p o rtin g A T P s y n th a s e α δ F6 oscp ATP ADP + Pi FUMARATE UQH2 UQ UQH2 NADH+H + CH2COO- C(OH)COO- CH2COO- CH(OH)COO- CHCOO- CH2COO- -OOCCOCH2CH2COO- -OOCCH2CH2CO.SCoA -OOCCOCH2COO- CH3CH(OH)CH2CO.SCoA -OOCCH=CHCOO- C C C Glyoxylate Cycle -OOCCHO GTP GDP ATP + HEME Protoporphyrinogen Coproporphyrinogen Uroporphyrinogen Porphobilinogen 5-Amino- levulinate COO- CH2 CH2 H2NCH2C=O FADH2 FAD Cyt.b Fe-S SUCCINATE II CH3COCOO- PYRUVATE Pi X Y Cyt.c1 Fe-S 2e- 2e- 1e- 1e- III 2UQ UQ UQH2 2UQH2 2UQ. _ UQ. _ Cyt.b L Cyt.b H Cyt.c IV Cu A Cu B Cu A 1.9.3.1 2e- Heme a Heme a 3 2H + 2H + 4H + 4H + 2H + NAD+ NADH+H+ NAD+ 1.1.1.39 1.2.4.1 2.3.1.12 3.1.3.43 4.1.1.32 4.1.3.7 4.2.1.3 1.1.1.41 1.2.4.2 2.3.1.61 6.2.1.4 -OOCCH2CH2COO- 1.3.5.1 4.2.1.2 1.1.1.37 6.4.1.1 4.1.3.8 4.1.3.1 4.1.3.2 ISOCITRATE 2.6.1.1 2.3.1.16 4.1.1.71 1.2.1.16 5.1.99.1 5.4.99.2 4.3.1.1 1.4.1.2 1.4.1.14 6.3.5.4 1.6.6.1 1.7.99.4 1.7.7.1 1.6.6.4 1.18.6.1 2.3.1.37 1.10.2.2 1.10.2.2 γ ε δ β H + + 3 3 β A T P ADP E N D ERGONIC REACTIO N 1.6.5.3 I FMNH2 FMN I 1.6. 5.3 2Fe -S (5 Clusters) H+ H+ H+ H+ ATP 4H + 2H + 2H + or H+ PHOTO- SYSTEM l O2 3.6.1.34 NADP + Glyceraldehyde Ribulose-1,5-bis-P 2 β 8 8 H + c 3 2 ε a 3 2 α 1 α ε α β 2 1 3 α α β 3 α β H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H + H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ Translocated protons H+ H+ H+ H+ P i Ferredoxin 4H+ PC PC PC PQH2 2PQH2 PQ _ . 2PQ _ . Fe-S Cyt.f PQ 2PQ Cyt bf 2e- 1e- 1e- 2e- 2e- 2e- 2e- C yclic P hotophosphorylatio n PQ PHOTO- SYSTEM II Cyt bc N o n -c y clic ele ctr o n flo w 2e- 2e- Mn 2e- * Protons from Water H 2 O H+ H+ 2H + 2H+ γ ATP synthase CO 2 Fixation H+ ADP Pi H+ NADPH+H + e e ATP THYLAKOID MEMBRANE CHLOROPLAST OUTER MEMBRANE THYLAKOID LUMEN STROMA (electric curre nt) P680 Chl.a QA QB Pheophytin P700 Chl.A0 A1 Fe-S ATP ADP ATP 1 / 2O2 H2O PQH2 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 hv VISION L I P I D P H O T O S Y N T H E S I S 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 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 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 CH3 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 HOCH2 C C C C CO OH OH H OH H H O HOCH2 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 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 )COOH 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 S-Adenosyl methionine (SAM) 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 CH2 P COO O-C-COO OH O OH OOC CH COCOO 2 N H HOC-CH(OH)CH(OH)CH2OP CH COO NH2 COO OH NH2 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 CH3 Ceramide Gangliosides NHCOR CH O 2 PP OPP CH2 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 HOCH2 C C C C CO OH H OH OH H O HOCH2 C C CO CO CO H NAD+ Pi ADP 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 CH3 CH O 3 CH O 3 n O O O O Phytol (C20) α-Tocopherol (Vitamin E) 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 + NAD( P) 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 OCH3 OCH3 CHOHCH OH 2 OH OCH3 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 OCH3 CH(OH)COO H2 NH3 + 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 NH2 CH OC NH N CH C O CH OC N H HN CH-CH3 C O OC NH HN CH2 CH2 CH2 C O OC NH HN C O CH OC NH HN C CH3 Methylmalonyl semialdehyde OHCCHCOO CH3 CH2 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 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 3.7.1.2 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 1.2.4.1 2.3.1.12 1.8.1.4 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 1.2.1.32 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 1.1.1.31 2.1.3.1 4.1.1.41 5.1.99.1 6.4.1.3 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 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 CH3 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 NH2 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 3-OH-Pentanoyl-CoA 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 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 CH3 CH COCHCOSCoA 3 CH3 CH CH=CHCOSCoA 3 CH3 CH CH(OH)CHCOSCoA 3 CH3 C(OH)CH(OH)COO CH CH 3 2 CH3 CH = CCOSCoA 2 CH3 HOCH CHCOS-CoA- 2 CH3 CH CHCO-SCoA 3 CH3 C (OH)CH(OH)COO CH3 CH3 CH CH CHCOSCoA 3 2 CH3 CH C = CHCOSCoA 3 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 1.1.1.85 Oxoleucine COOH (CH ) CHCHCH(OH)COO 32 S-Adenosylmethyl thiopropylamine (Decarboxylated SAM) PROLINE Coenzyme A CH C= CHCH 3 2 CH3 O CH CH 3 3 HO CH3 CH3 CH3 CH C-CH HO 3 2 2 C PP CH2 CH C= CHCH O 2 2 PP CH3 3-P-Glycerol Phosphatidyl ethanolamine CEPHALIN 3.1.4.12 2.7.8.3 Progesterone 1.5.1.12 2.7.3.2 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 5.1.1.7 2.7.1.40 4.1.3.18 4.1.3.18 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 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 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 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 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 4.2.1.52 1.2.1.18 4.2.1.18 O CH C CH OC N HN DP CH C O CH OC N HN RPPP OCH2 H C C H OH OH CH N HN C H C P H O OCH2 C C H OH H OH C H C C C NH2 C CH HC N RP(PP) N N N + P NH2 H O OCH2 C C H OH H OH C H C C OC C CH HC N RP N N NH P H OCH2 C C H OH OH CO CH2 C CONH2 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 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 Carbamoyl-P 2.3.1.9 Carnitine 2.6.1.4 2.6.1.44 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 Menaquinone 4.1.1.15 2.6.1.19 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 NH CH CH(NH )COO 2 3 HO + O OH OH HO OPPU COO - O OH OH HO OPPU COO - OH H OH HOCH2 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 NHCOCH3 P CH OH 2 CH OH 2 CH OH 2 O OH HO OH NH2 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 CH2 CH OP 2 OH H H H OH C C C C OH OH H COO - HOCH2 H OH OH OH C C C CHO H H HOCH2 H OH OH H C C C CHO H OH HOCH2 OH H OH H C C C CHO H OH HOCH2 H OH H OH C C C CHO OH H HOCH2 OH H H OH C C C CHO OH H HOCH2 OH H OH OH C C C CHO H H HOCH2 H OH H OH C C C C OH H H OH COO - POCH2 OH H OH C C CO H POCH2 CH OH 2 H OH H C C CO OH HOCH2 CH OH 2 CH OH 2 POCH2 H OH OH C C CO H CH OH 2 POCH2 OH H H C C CO OH CH OH 2 POCH2 H OH OH C C CO H HOCH2 CH OH 2 OH H OH C C CO H HOCH2 CH OH 2 OH H H C C CO OH HOCH2 CH OH 2 H OH OH H C C C H OH HOCH2 CH OH 2 OH H OH OH C C C H H HOCH2 CH OH 2 H OH H OH C C C C OH H H OH CH OH 2 HOCH2 H OH OH C C CHO H POCH2 H OH H OH C C C CO OH H HOCH2 CH O 2 P H OH OH OH C C C H H HOCH2 CH OH 2 H OH OH C C C H CO H HO POCH2 CH OH 2 P H OH OH C C C H CO H HO CH O 2 P OCH2 H OH OH C C H C CHO OH H POCH2 POCH2 O OH NH2 OH CH O 2 P CHOHCHO POCH2 HOCH 2 COCH 2 OP O OH OO P P OH CH O 2 P CHOHCOOP POCH2 CHOH POCH2 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 2nCH=CHCOS-CoA CH (CH ) 3 25 2 CH=CHCH COSACP CH (CH ) 3 26CH=CHCOSACP CH (CH ) 3 26COCH 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 26CH(OH)CH COSACP 2 CH CH=CHCO.S-ACP 3 CH (CH ) 3 22 2 COCH COSACP CH3COCH 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 ACYL-CoA (Mitochondria) 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 Pentenoyl-CoA 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 CH2 CH2 R'-CO-OCH O-CO-R O-PO O- HOCH CH 2 2 NH3 + POCH CH 2 2NH3 + CPP- OCH CH 2 2NH3 + O - CH O-CO-R 2 CH O P 2 OCH CH 2 2NH3 + 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 NH2 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 NH2 RPPP CH C CH OC N N NH2 C C C CH RP(P) HC N N N N NH2 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 + + CH3 CH3 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 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 NH 3 + 4.1.1.70 H NCONH 2 2 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 ) 2 2 33 + 1.2.1.41 UDP-N-Ac-Muramate O O CH CH 3 COO- NHAC HO OPPU CH OH 2 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 CH CH CH2 HC 3 HC 3 HC 3 HC C C H H Fe CH2 CH2 COO - - CH3 CH3 CH2 CH2 CH2 HC 3 HC 3 N H N H N H N H CH CH HC 2 C C H2 H2 - CH2 CH2 COO CH2 CH2 COO - HC 2 HC 2 CH2 CH2 OOC COO HN 2 N H - - CH2 HC 2 HC 2 HC 2 H2 H2 CH2 CH2 CH2 CH2 CH2 CH2 N H N H N H N H COO COO COO COO C C - - CH2 CH2 COO CH2 CH2 COO - - - - OOC - OOC - CH3 CH3 HC 3 HC 3 HC 2 H2 H2 N H N H N H N H CH2 CH2 CH2 CH2 CH2 C C COO- CH2 CH2 COO CH2 CH2 COO - - COO- COO- CH C(OH)CH CH O 3 2 2 PP CH COO 2 OHCCOO HOCH COO 2 NH2 H NCNHCH COO 2 2 + NH2 H NCN(CH )CH COO 2 3 2 + NH2 HNCN(CH )CH COO 3 2 P- + HN C NH CO N CH2 CH3 OOCCHCH COO 2 H NCNHCH CH CH CH 2 2 2 2 N (NH ) 3 + COO CHCOO HC CH2 HOCH N OOCCH(OH)CH CH(NH )COO 2 3 + CHCOO CH2 HOCH HC 2 N H NH CHCOO CH2 CH2 CH2 OOCCH(OH)CH COCOO 2 N CHCOO CH2 CH2 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 (NH3 + OOC-CH-COSCoA CH3 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 + H N(CH ) 2 4 2 CH(NH )COO 3 CH(NH3 + (CH ) N(CH ) 33 23CH CH(NH )COO 2 3 + + CH2 C H OOCC N HC CH-COO CH2 C H2 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 NH3 + OOCCH-CH CH CH CHCOO 2 2 2 NH3 + NH3 + (CH ) CHC(OH)CH 32 2 COOH COO (CH ) CHCH COCOO 32 2 + (CH ) CHCH 32 2 CH(NH )COO 3 HOCH CHCOO 2 CH3 CHCOCOO CH3 CH3 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 CH2COO 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 CH3 CH + CH(NH )COO 3 CH COC(OH)CH CH 3 2 3 COO CHCOCOO CH CH 3 2 CH3 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 NH2 CH2 H NCH CH COO 2 2 2 H NCH 2 2 CH3 CHCOO H NCONHCH CHCOO 2 2 CH3 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 CH2 N N N N O OH OH NH2 HC CH N N N N O O P O O O CH2 OH NH2 HC CH COO CO NH OC N H C H HN 2 NH2 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 CH2 P COO OH O O O COO O CH COO 2 O CH COO 2 -OOC OCH2 CH2 OH H C P HOCH HCOH OC COO COO HO OH OH O NH2 COO OCH NH CH COCOO 2 NH CHO CO NH2 OH CH CH(NH )COO 2 3 + N COO COO N + COO COO RP O OH OH HO OPPU COO O OH NHCOCH3 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 O HO OH COO CH(O ) P POCH2 COO CH(OH) HOCH2 COO COO CH(O ) P HOCH2 COO CH =C(O ) 2 P COO CONH2 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 CH3 (CH ) N(CH ) 33 23CH 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 PGE2 OH HOCH2 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 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 2.4.1.17 Diacyl glycerol 2.3.1.6 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 COO- 2 OHCCH 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 ORNITHINE ARGININE HYDROXY PROLINE PHOSPHATIDYL SERINE Phosphatidyl inositol LECITHIN SPHINGOMYELIN STEROIDS Pregnenolone 2.7.6.1 2.4.2.14 6.3.4.7 5.3.1.9 3.1.3.11 1.2.1.13 2.7.2.3 H OH OH C C C H CO OH C H H OH POCH2 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 2.3.1.38 ATP NADH SUCROSE ADENOSINE-P (AMP) Triacylglycerol FAT RNA CH3 CH2 OC-COO OH COO CH CH 2 COO (NH ) 3 + GLYCOPROTEINS GANGLIOSIDES MUCINS 4.1.2.- 2.6.1.- GLUCOSE O-Acyl-carnitine O-Acyl-carnitine OH O - - R-CO-OCH 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 3.1.3.4 2.7.1.107 NH2 + + H NCNHCH CH CH CH 2 2 2 2 COO (NH ) 3 H OH H OH C C C CO OH H HOCH2 CH OH 2 R-CH2 COO CH O-CO-R 2 CH O-CO-R" 2 R’-CO-OCH OH O CH CHNH 2 3 + O R'-CO-OCH O- CH O-CO-R 2 CH O PO 2 COO OOCCH CH CH 2 2 COO (NH ) 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 1.3.1.13 4.1.1.28 Malonic semi- aldehyde 2.7.2.4 2.1.3.3 3.5.1.2 6.3.1.2 6.3.5.5 Carbohydrates Biosynthesis Degradation Amino Acids Biosynthesis Degradation Lipids Biosynthesis Degradation Purines & Pyrimidines Biosynthesis Degradation Biosynthesis Degradation Vitamins Co-enzymes & Hormones Pentose Phosphate Pathway Photosynthesis Dark Reactions COMPARTMENTATION The "Backbone" of metabolism involves GLYCOLYSIS in the CYTOPLASM, the TCA CYCLE (mainly) in the Mitochondrial matrix and ATP FORMATION spanning the MITOCHONDRIAL INNER MEMBRANE An electron flow (an electric current) generated from NADH and UQH2 drives the translocation of protons from the matrix to the intermembrane space. The retrolocation of these protons through the F0 subunits of ATP synthase to the matrix then supplies the energy needed to form ATP from ADP and phosphate Electron Flow Proton Flow Small Numbers ( eg. 2.4.6.7) refer to the IUBMBEnzyme Commission (EC) Reference Numbers of Enzymes LEGEND Human Metabolism is identified as far possible by black arrows Biosynthesis Degradation HEMOGLOBIN CHLOROPHYLL ATP TR A N S L O C A T E D PROTONS 2.7.1.1 ATP 2.7.1.2 Argentina SIGMA-ALDRICH DE ARGENTINA S.A. Free Tel: 0810 888 7446 Tel: (+54) 11 4556 1472 Fax: (+54) 11 4552 1698 Australia SIGMA-ALDRICH PTY LTD. Free Tel: 1800 800 097 Free Fax: 1800 800 096 Tel: (+61) 2 9841 0555 Fax: (+61) 2 9841 0500 Austria SIGMA-ALDRICH HANDELS GmbH Tel: (+43) 1 605 81 10 Fax: (+43) 1 605 81 20 Belgium SIGMA-ALDRICH NV/S.A. Free Tel: 0800 14747 Free Fax: 0800 14745 Tel: (+32) 3 899 13 01 Fax: (+32) 3 899 13 11 Brazil SIGMA-ALDRICH BRASIL LTDA. Free Tel: 0800 701 7425 Tel: (+55) 11 3732 3100 Fax: (+55) 11 5522 9895 Canada SIGMA-ALDRICH CANADA LTD. Free Tel: 1800 565 1400 Free Fax: 1800 265 3858 Tel: (+1) 905 829 9500 Fax: (+1) 905 829 9292 Chile SIGMA-ALDRICH QUIMICA LIMITADA Tel: (+56) 2 495 7395 Fax: (+56) 2 495 7396 China SIGMA-ALDRICH (SHANGHAI) TRADING CO. LTD. Free Tel: 800 819 3336 Tel: (+86) 21 6141 5566 Fax: (+86) 21 6141 5567 Czech Republic SIGMA-ALDRICH spol. s r. o. Tel: (+420) 246 003 200 Fax: (+420) 246 003 291 Denmark SIGMA-ALDRICH DENMARK A/S Tel: (+45) 43 56 59 00 Fax: (+45) 43 56 59 05 Finland SIGMA-ALDRICH FINLAND OY Tel: (+358) 9 350 9250 Fax: (+358) 9 350 92555 France SIGMA-ALDRICH CHIMIE S.à.r.l. Free Tel: 0800 211 408 Free Fax: 0800 031 052 Tel: (+33) 474 82 28 00 Fax: (+33) 474 95 68 08 Germany SIGMA-ALDRICH CHEMIE GmbH Free Tel: 0800 51 55 000 Free Fax: 0800 64 90 000 Tel: (+49) 89 6513 0 Fax: (+49) 89 6513 1160 Greece SIGMA-ALDRICH (O.M.) LTD. Tel: (+30) 210 994 8010 Fax: (+30) 210 994 3831 Hungary SIGMA-ALDRICH Kft Ingyenes telefonszám: 06 80 355 355 Ingyenes fax szám: 06 80 344 344 Tel: (+36) 1 235 9055 Fax: (+36) 1 235 9050 India SIGMA-ALDRICH CHEMICALS PRIVATE LIMITED Telephone Bangalore: (+91) 80 6621 9400 New Delhi: (+91) 11 4358 8000 Mumbai: (+91) 22 2570 2364 Hyderabad: (+91) 40 4015 5488 Kolkata: (+91) 33 4013 8003 Fax Bangalore: (+91) 80 6621 9650 New Delhi: (+91) 11 4358 8001 Mumbai: (+91) 22 2579 7589 Hyderabad: (+91) 40 4015 5466 Kolkata: (+91) 33 4013 8016 Ireland SIGMA-ALDRICH IRELAND LTD. Free Tel: 1800 200 888 Free Fax: 1800 600 222 Tel: (+353) 402 20370 Fax: (+ 353) 402 20375 Israel SIGMA-ALDRICH ISRAEL LTD. Free Tel: 1 800 70 2222 Tel: (+972) 8 948 4100 Fax: (+972) 8 948 4200 Italy SIGMA-ALDRICH S.r.l. Numero Verde: 800 827018 Tel: (+39) 02 3341 7310 Fax: (+39) 02 3801 0737 Japan SIGMA-ALDRICH JAPAN K.K. Tel: (+81) 3 5796 7300 Fax: (+81) 3 5796 7315 Korea SIGMA-ALDRICH KOREA Free Tel: (+82) 80 023 7111 Free Fax: (+82) 80 023 8111 Tel: (+82) 31 329 9000 Fax: (+82) 31 329 9090 Malaysia SIGMA-ALDRICH (M) SDN. BHD Tel: (+60) 3 5635 3321 Fax: (+60) 3 5635 4116 Mexico SIGMA-ALDRICH QUÍMICA, S.A. de C.V. Free Tel: 01 800 007 5300 Free Fax: 01 800 712 9920 Tel: (+52) 722 276 1600 Fax: (+52) 722 276 1601 The Netherlands SIGMA-ALDRICH CHEMIE BV Free Tel: 0800 022 9088 Free Fax: 0800 022 9089 Tel: (+31) 78 620 5411 Fax: (+31) 78 620 5421 New Zealand SIGMA-ALDRICH NEW ZEALAND LTD. Free Tel: 0800 936 666 Free Fax: 0800 937 777 Tel: (+61) 2 9841 0555 Fax: (+61) 2 9841 0500 Norway SIGMA-ALDRICH NORWAY AS Tel: (+47) 23 17 60 00 Fax: (+47) 23 17 60 10 Poland SIGMA-ALDRICH Sp. z o.o. Tel: (+48) 61 829 01 00 Fax: (+48) 61 829 01 20 Portugal SIGMA-ALDRICH QUÍMICA, S.A. Free Tel: 800 202 180 Free Fax: 800 202 178 Tel: (+351) 21 924 2555 Fax: (+351) 21 924 2610 Russia SIGMA-ALDRICH RUS, LLC Tel: (+7) 495 621 5579 Fax: (+7) 495 621 5923 Singapore SIGMA-ALDRICH PTE. LTD. Tel: (+65) 6779 1200 Fax: (+65) 6779 1822 Slovakia SIGMA-ALDRICH spol. s r. o. Tel: (+421) 255 571 562 Fax: (+421) 255 571 564 South Africa SIGMA-ALDRICH (PTY) LTD. Free Tel: 0800 1100 75 Free Fax: 0800 1100 79 Tel: (+27) 11 979 1188 Fax: (+27) 11 979 1119 Spain SIGMA-ALDRICH QUÍMICA, S.A. Free Tel: 900 101 376 Free Fax: 900 102 028 Tel: (+34) 91 661 99 77 Fax: (+34) 91 661 96 42 Sweden SIGMA-ALDRICH SWEDEN AB Tel: (+46) 8 742 4200 Fax: (+46) 8 742 4243 Switzerland SIGMA-ALDRICH CHEMIE GmbH Free Tel: 0800 80 00 80 Free Fax: 0800 80 00 81 Tel: (+41) 81 755 2828 Fax: (+41) 81 755 2815 United Kingdom SIGMA-ALDRICH COMPANY LTD. Free Tel: 0800 717 181 Free Fax: 0800 378 785 Tel: (+44) 1747 833 000 Fax: (+44) 1747 833 313 United States SIGMA-ALDRICH Toll-Free: 800 325 3010 Toll-Free Fax: 800 325 5052 Tel: (+1) 314 771 5765 Fax: (+1) 314 771 5757 Vietnam SIGMA-ALDRICH PTE LTD. VN R.O. Tel: (+84) 3516 2810 Fax: (+84) 6258 4238 Internet sigma-aldrich.com © 2003 International Union of Biochemistry and Molecular Biology www.iubmb.org 22 nd Edition Designed by Donald E. Nicholson, D.Sc., The University of Leeds, England – and Sigma-Aldrich Cat. No. M3782 sigma-aldrich.com/metpath Metabolic Pathways

Transcript of Metabolic Pathways Poster (3 MB)

Page 1: Metabolic Pathways Poster (3 MB)

2H+

H+

OXALOACETATE

PYRUVATE

SUCCINYL-CoA

GLUTARATE

CITRATE

MALATE2-OXO- ASPARTATE

NO2-

NO3-

N2

NH4

CH3COSCoA

ACETYL-CoA

HOH

CO2

NAD

TRANSAMINATION

2H+

2H+

+

CO2

5-Amino-levulinate

Glycine

H+H+

H+H+

H+H+

c

H+ H+a

F0

F1

F1

β2

1 αβ

α

γ

10 c-sub-units

AD P+ Pi

a H+

3.6.1.34

H+-tra

nsporting ATP synthase

α

δF6

oscp

ATP

ADP +Pi

FUMARATE

UQH2

UQ

UQH2

NADH+H+CH2COO-C(OH)COO-CH2COO-

CH(OH)COO-CHCOO-CH2COO-

-OOCCOCH2CH2COO-

-OOCCH2CH2CO.SCoA

-OOCCOCH2COO-

CH3CH(OH)CH2CO.SCoA

-OOCCH=CHCOO-

CCCC

Glyoxylate Cycle

-OOCCHO

GTP

GDPATP

+

HEME Protoporphyrinogen Coproporphyrinogen Uroporphyrinogen Porphobilinogen

5-Amino-levulinate

COO-CH2CH2

H2NCH2C=O

FADH2

FADCyt.b

Fe-S

SUCCINATEII

CH3COCOO-

PYRUVATE

Pi

X Y

Cyt.c1

Fe-S

2e-2e-

1e-

1e-

III

2UQ UQ

UQH22UQH2

2UQ._

UQ._

Cyt.bL Cyt.bH

Cyt.c

IV

CuA

CuB

CuA

1.9.3.1

2e-

Heme a

Heme a3

2H+

2H+4H+

4H+

2H+

NAD+

NADH+H+

NAD+

1.1.1.39

1.2.4.12.3.1.123.1.3.43

4.1.1.32

4.1.3.7

4.2.1.3

1.1.1.41

1.2.4.22.3.1.61

6.2.1.4-OOCCH2CH2COO-

1.3.5.1

4.2.1.2

1.1.1.37

6.4.1.1

4.1.3.8

4.1.3.1

4.1.3.2

ISOCITRATE

2.6.1.12.3.1.16

4.1.1.71

1.2.1.16

5.1.99.15.4.99.2

4.3.1.1

1.4.1.2 1.4.1.14

6.3.5.4

1.6.6.11.7.99.4 1.7.7.1

1.6.6.4

1.18.6.1

2.3.1.37

1.10.2.2

1.10.2.2

γ

εδ

β

H++

33 β

ATP

ADP

ENDERGONIC REACTION

1.6.5.3

I

FMNH2

FMN I

1.6. 5.3

2Fe -S (5 Clusters)

H+ H+H+ H+

ATP

4H+

2H+

2H+or

H+

PHOTO-SYSTEM

l

O2

3.6.1.34

NADP+

GlyceraldehydeRibulose-1,5-bis-P

88

H+c

32

ε

a

32

α1

α

ε

α

β2

1

3

α

αβ

3

α

β

H+

H+

H+

H+

H+H+

H+

H+ H+H+

H+H+H+H+

H+

H+H+H+

H+H+

H+

H+

H+

H+

H+

H+H+

H+H+

H+H+

H+H+H+Translocated protons

H+

H+H+

H+Pi

Ferredoxin

4H+PC PC

PC

PQH2

2PQH2

PQ_.

2PQ_.Fe-S Cyt.f

PQ

2PQ

Cyt bf

2e-

1e- 1e-

2e-

2e-

2e-

2e-

Cyclic Photophosphorylation

PQ

PHOTO-SYSTEM II

Cyt bc

Non-cyclic electron flow

2e-2e-

Mn2e-

*

Protons from Water

H2O

H+

H+

2H+

2H+

γ

ATP synthase

CO2Fixation

H+

ADPPi

H+

NADPH+H+

eeeATPTHYLAKOID MEMBRANE

CHLOROPLAST OUTER MEMBRANE

THYLAKOID LUMEN

STROMA

(electric current)

P680Chl.a

QA

QB

Pheophytin

P700

Chl.A0

A1

Fe-S

ATP

ADP

ATP

1/2O2

H2O

PQH2

To Brain -

AMINO

ACIDS

PYRIMIDINES

PURINES

CATECHOLAMINES

AROMATIC

AMINO

ACIDS

hvVISION

LIPID

PHOTOSYNTHESIS

PORPHYRINS

STEROIDS

ISOPRENOIDS

PHOSPHOLIPIDS

DEGRADATION

LIPID

BIOSYNTHESIS

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 23-OH-ButyrateAcetone

Acetoacetate

KETONE BODIES

HYALURONIC ACID DERMATAN BLOOD GROUPSUBSTANCESPEPTIDO-

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

HOCHP

Glycerol

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

NHIndole-

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 )COOH2 3+

Histidinol-PHistidinolHistidinal3.1.3.15 2.6.1.91.1.1.23

3.6.1.315.3.1.162.4.2.17

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

Cysteate S-Adenosylhomocysteine

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

S-Adenosylmethionine

(SAM)

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

Cysteinesulphinate

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-ACP2Malonyl-ACP

HOOCCH CO-SCoA2Malonyl-Co-A

CH CO-S-ACP3

Acetyl-ACP

CH O-CO-R2

CH OH2

R’-CO-OCH

FATTY ACIDACYL-CoA(Cytosol)

CH O-CO-R2

CH O2

R’-CO-OCH

P

Cardiolipin Phosphatidylglycerol

AcetylcholineGlycerophosphocholineLysolecithin

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

GangliosidesNHCOR

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

ADPADP

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)

OpsinCHO

CH OH2

CHO

CH OH2

CH3CH O3CH O3 n

O

O

O

O

Phytol (C20)

α-Tocopherol(Vitamin E)

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

+NAD( P)

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

OHOCH3

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 PNHCOCH 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

NH RP

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

NH RP

NH

OCH 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

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

1.1.1.92.7.1.15

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 CHO2Glycol

aldehyde

Ethanolamine-P

2.7.1.30

2.3.1.7

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

3.1.4.33.1.4.4

2.7.7.15

3.1.1.5 3.1.4.2

2.7.1.32

2.7.1.82

1.2.4.12.3.1.121.8.1.4

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

4.3.1.8

4.2.1.75

4.1.1.371.3.3.31.3.3.4

4.99.1.1

2.5.1.29

2.4.1.47

4.1.1.28 2.3.1.5 2.1.1.4

6.3.5.16.3.1.5

2.4.2.112.7.7.18

2.6.1.5

1.2.1.32

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 1.1.3.221.1.3.22

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

4.4.1.11.6.4.1

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 2Propanoyl-CoA

1.1.1.31

2.1.3.14.1.1.415.1.99.1

6.4.1.3

6.3.2.5

2.1.1.142.1.1.13

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

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

2.7.7.62.7.7.62.7.7.6

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 3-OH-Pentanoyl-CoA

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

2-OXO ACID

Glutamyl-P

Glutamine

UREA

P-CreatineCreatine Creatinine

Glycine

CITRULLINE

Glutamicsemialdehyde

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

1.2.1.114.2.1.52 1.3.1.26 Piperideine-

2, 6-dicarboxylateN-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

CH3CH CH=CHCOSCoA3

CH3CH CH(OH)CHCOSCoA3

CH3

C(OH)CH(OH)COOCH CH3 2

CH3

CH = CCOSCoA2

CH3HOCH CHCOS-CoA-2

CH3CH 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

4.2.1.173.1.2.4

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

5.1.1.7

2.7.1.40

4.1.3.18

4.1.3.18

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

2.1.1.102.1.1.20

1.1.1.3

1.1.1.3

4.2.1.18

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

1.4.3.41.14.18.1

1.14.16.2

Hexanoyl-CoA

Butanoyl-CoA

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

4.2.1.521.2.1.18

4.2.1.18

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 CCONH2

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

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

N H

HN

CCO

CCH

N

N

N

HN

RPH N2 C

2.7.4.6

1.17.4.1

2.7.4.6

2.6.1.13Carbamoyl-P

2.3.1.9

Carnitine

2.6.1.4 2.6.1.44

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

Menaquinone

4.1.1.15

2.6.1.19

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

NH

CH CH(NH )COO2 3HO+

O

OH

OH

HO

OPPU

COO-

O

OHOH

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

OHOPPU

CH OH2

O

O

HO

OH

OH

HO

P

CH OH2

CH OH2 O

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

HOCH2

H

OH OHH

C C C CHO

HOH

HOCH2

OH

H OHH

C C C CHO

HOH

HOCH2

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

HOCH2

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

HOCH2 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

HOCH2 CH OH2

OH

H OH

C C CO

H

HOCH2CH OH2

OH

H H

C C CO

OH

HOCH2 CH OH2

H

OH OHH

C C C

HOH

HOCH2 CH OH2

OH

H OHOH

C C C

HH

HOCH2 CH OH2

H

OH HOH

C C C C

OHH H

OH

CH OH2HOCH2

H

OH OHC C CHO

H

POCH2

H

OH HOH

C C C CO

OHH

HOCH2 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

HOCH2COCH2OP

O

OH

O OP P

OH

CH O2 PCHOHCOOPPOCH2

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

ACYL-CoA(Mitochondria)

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 2Pentenoyl-CoACH 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

R'-CO-OCH

O-CO-R

O-POO-

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 CH2 COO(NH )3+

OHOH

CH CH2 COO-(NH )3+

CO

NH2

CH CH(NH )COO2 3+

NHOC

CO

NHOC

NH

CH

H N2

HCCH

N

N

CRP

H N2

CHC

CHOC N

N

DP

NH2

RPPP

CHC

CHOCN

N

NH2

CC

CCH

RP(P)HC

N

N

N

NNH2

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 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 2

NH3+

4.1.1.70

H NCONH2 2

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 )2 2 3 3+

1.2.1.41

UDP-N-Ac-Muramate

O

OCH 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

2.7.7.125.1.3.2

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

CHCH

CH2

H C3

H C3H C3

HC

C

C

H

H

Fe

CH2CH2COO- -

CH3

CH3

CH2

CH2

CH2

H C3

H C3NH

NH

NH

NH

CH

CH

H C2

C

CH2

H2

-

CH2CH2COO

CH2CH2COO -

H C2

H C2

CH 2

CH 2

OOC

COO

H N2

NH

-

-

CH2

H C2

H C2

H C2

H2

H2

CH2CH2 CH2

CH2

CH2

CH2

NH

NH

NH

NH

COO

COO

COOCOO

C

C

--

CH2CH2COO

CH2CH2COO- -

-

-

OOC-

OOC-

CH3

CH3

H C3

H C3

H C2

H2

H2

NH

NH

NH

NHCH2

CH2

CH2

CH2

CH2

C

C

COO-

CH2CH2COO

CH2CH2COO- -

COO-

COO-

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

+ NH2HNCN(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

NCHCOO

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 (NH3+

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+

H N(CH )2 42 CH(NH )COO3CH(NH3++

(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 2NH3

+

NH3+

(CH ) CHC(OH)CH3 2 2

COOH

COO (CH ) CHCH COCOO3 2 2

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

HOCH CHCOO2

CH3

CHCOCOOCH3

CH3CH 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 CH2COO2

+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

CH3CH

+CH(NH )COO3

CH COC(OH)CH CH3 2 3

COO CHCOCOOCH 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 CHCOO2NHCOCH 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

CRPRP

H N2

OOCC

CHN RP

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+

N

COOCOO

N+

COOCOO

RP

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 2Dimethylglycine

1.1.99.1

1.2.1.8

COOHO HO COO

O

HO OH

COO

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

CH(O )PHOCH2 COO

CH =C(O )2 P COO

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 CH2 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

CH3

(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 POCMP2O

CH CH N(CH )2 2 3+

OHOCH

CH OPO2

CH OH2

O-

CH OPO2

OCH OCH=CHR2

CH CH N(CH )2 2 3 3+

O- CH OPO2

OR'-CO-OCHCH O-CO-R2 3.1.1.32

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

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

2.4.1.17

Diacylglycerol

2.3.1.6

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

COO-2OHCCH

2.1.4.1

2.4.99.7

5.1.3.12

1.1.1.132

4.2.1.462.7.1.7

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

ORNITHINE

ARGININEHYDROXYPROLINE

PHOSPHATIDYLSERINEPhosphatidyl

inositol

LECITHIN

SPHINGOMYELIN

STEROIDS

Pregnenolone

2.7.6.1

2.4.2.146.3.4.7

5.3.1.9

3.1.3.11

1.2.1.13

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

POO

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

2.3.1.38

ATP

NADH

SUCROSE

ADENOSINE-P(AMP)

TriacylglycerolFAT

RNA

CH3

CH2

OC-COOOH

COO

CH CH2 COO(NH )3+

GLYCOPROTEINSGANGLIOSIDES

MUCINS

4.1.2.-

2.6.1.-

GLUCOSE

O-Acyl-carnitine

O-Acyl-carnitine

OH

O-

-

R-CO-OCH

R'-CO-OCH

R'-CO-OCH

O HCO-CO-R

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

CH O-CO-R’2OR'-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 3.1.3.4 2.7.1.107

NH2+

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

H

OH HOH

C C C CO

OHH

HOCH2CH OH2

R-CH2COO

CH O-CO-R2

CH O-CO-R"2

R’-CO-OCH

OH

O

CH CHNH2 3+

OR'-CO-OCH

O-

CH O-CO-R2

CH O PO2

COO

OOCCH CH CH2 2 COO(NH )3

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

O

OHHO

OH

OH

CH OH2CH OH2

NH

CH O-CO-R2

1.3.1.13

4.1.1.28

Malonicsemi-

aldehyde

2.7.2.4

2.1.3.3

3.5.1.26.3.1.2

6.3.5.

5

CarbohydratesBiosynthesisDegradation

Amino AcidsBiosynthesisDegradation

LipidsBiosynthesisDegradation

Purines &Pyrimidines

BiosynthesisDegradation

Biosynthesis DegradationVitamins Co-enzymes & Hormones

Pentose Phosphate Pathway

Photosynthesis Dark Reactions

COMPARTMENTATIONThe "Backbone" of metabolism involves

GLYCOLYSIS in the CYTOPLASM,the TCA CYCLE (mainly) in the Mitochondrial matrix

and ATP FORMATION spanning theMITOCHONDRIAL INNER MEMBRANE

An electron flow (an electric current) generated fromNADH and UQH2 drives the translocation of protons

from the matrix to the intermembrane space.The retrolocation of these protons through the F0 subunits

of ATP synthase to the matrix then supplies the energyneeded to form ATP from ADP and phosphate

Electron Flow Proton Flow

Small Numbers ( eg. 2.4.6.7) refer to the IUBMBEnzymeCommission (EC) Reference Numbers of Enzymes

LEGEND

Human Metabolism is identified as far possible by black arrowsBiosynthesis Degradation

HEMOGLOBIN CHLOROPHYLL

ATP

TRA

NS

LOCATED PROTONS

2.7.1.1

ATP2.7.1.2

ArgentinaSIGMA-ALDRICH DE ARGENTINA S.A. Free Tel: 0810 888 7446 Tel: (+54) 11 4556 1472 Fax: (+54) 11 4552 1698

AustraliaSIGMA-ALDRICH PTY LTD. Free Tel: 1800 800 097 Free Fax: 1800 800 096 Tel: (+61) 2 9841 0555 Fax: (+61) 2 9841 0500

AustriaSIGMA-ALDRICH HANDELS GmbH Tel: (+43) 1 605 81 10 Fax: (+43) 1 605 81 20

BelgiumSIGMA-ALDRICH NV/S.A.Free Tel: 0800 14747 Free Fax: 0800 14745 Tel: (+32) 3 899 13 01 Fax: (+32) 3 899 13 11

BrazilSIGMA-ALDRICH BRASIL LTDA.Free Tel: 0800 701 7425 Tel: (+55) 11 3732 3100 Fax: (+55) 11 5522 9895

CanadaSIGMA-ALDRICH CANADA LTD.Free Tel: 1800 565 1400 Free Fax: 1800 265 3858 Tel: (+1) 905 829 9500 Fax: (+1) 905 829 9292

ChileSIGMA-ALDRICH QUIMICA LIMITADATel: (+56) 2 495 7395 Fax: (+56) 2 495 7396

ChinaSIGMA-ALDRICH (SHANGHAI) TRADING CO. LTD.Free Tel: 800 819 3336 Tel: (+86) 21 6141 5566 Fax: (+86) 21 6141 5567

Czech RepublicSIGMA-ALDRICH spol. s r. o. Tel: (+420) 246 003 200 Fax: (+420) 246 003 291

DenmarkSIGMA-ALDRICH DENMARK A/S Tel: (+45) 43 56 59 00 Fax: (+45) 43 56 59 05

FinlandSIGMA-ALDRICH FINLAND OYTel: (+358) 9 350 9250 Fax: (+358) 9 350 92555

FranceSIGMA-ALDRICH CHIMIE S.à.r.l. Free Tel: 0800 211 408Free Fax: 0800 031 052Tel: (+33) 474 82 28 00 Fax: (+33) 474 95 68 08

GermanySIGMA-ALDRICH CHEMIE GmbHFree Tel: 0800 51 55 000 Free Fax: 0800 64 90 000 Tel: (+49) 89 6513 0 Fax: (+49) 89 6513 1160

GreeceSIGMA-ALDRICH (O.M.) LTD.Tel: (+30) 210 994 8010 Fax: (+30) 210 994 3831

HungarySIGMA-ALDRICH Kft Ingyenes telefonszám: 06 80 355 355 Ingyenes fax szám: 06 80 344 344 Tel: (+36) 1 235 9055 Fax: (+36) 1 235 9050

IndiaSIGMA-ALDRICH CHEMICALS PRIVATE LIMITED Telephone Bangalore: (+91) 80 6621 9400 New Delhi: (+91) 11 4358 8000 Mumbai: (+91) 22 2570 2364 Hyderabad: (+91) 40 4015 5488Kolkata: (+91) 33 4013 8003 Fax Bangalore: (+91) 80 6621 9650 New Delhi: (+91) 11 4358 8001 Mumbai: (+91) 22 2579 7589 Hyderabad: (+91) 40 4015 5466Kolkata: (+91) 33 4013 8016

IrelandSIGMA-ALDRICH IRELAND LTD. Free Tel: 1800 200 888 Free Fax: 1800 600 222Tel: (+353) 402 20370Fax: (+ 353) 402 20375

IsraelSIGMA-ALDRICH ISRAEL LTD. Free Tel: 1 800 70 2222 Tel: (+972) 8 948 4100 Fax: (+972) 8 948 4200

ItalySIGMA-ALDRICH S.r.l. Numero Verde: 800 827018 Tel: (+39) 02 3341 7310 Fax: (+39) 02 3801 0737

JapanSIGMA-ALDRICH JAPAN K.K. Tel: (+81) 3 5796 7300 Fax: (+81) 3 5796 7315

KoreaSIGMA-ALDRICH KOREA Free Tel: (+82) 80 023 7111 Free Fax: (+82) 80 023 8111 Tel: (+82) 31 329 9000 Fax: (+82) 31 329 9090

MalaysiaSIGMA-ALDRICH (M) SDN. BHDTel: (+60) 3 5635 3321 Fax: (+60) 3 5635 4116

MexicoSIGMA-ALDRICH QUÍMICA, S.A. de C.V.Free Tel: 01 800 007 5300 Free Fax: 01 800 712 9920 Tel: (+52) 722 276 1600 Fax: (+52) 722 276 1601

The NetherlandsSIGMA-ALDRICH CHEMIE BVFree Tel: 0800 022 9088 Free Fax: 0800 022 9089 Tel: (+31) 78 620 5411 Fax: (+31) 78 620 5421

New ZealandSIGMA-ALDRICH NEW ZEALAND LTD. Free Tel: 0800 936 666 Free Fax: 0800 937 777 Tel: (+61) 2 9841 0555 Fax: (+61) 2 9841 0500

NorwaySIGMA-ALDRICH NORWAY AS Tel: (+47) 23 17 60 00 Fax: (+47) 23 17 60 10

PolandSIGMA-ALDRICH Sp. z o.o. Tel: (+48) 61 829 01 00 Fax: (+48) 61 829 01 20

PortugalSIGMA-ALDRICH QUÍMICA, S.A.Free Tel: 800 202 180 Free Fax: 800 202 178 Tel: (+351) 21 924 2555 Fax: (+351) 21 924 2610

RussiaSIGMA-ALDRICH RUS, LLC Tel: (+7) 495 621 5579 Fax: (+7) 495 621 5923

SingaporeSIGMA-ALDRICH PTE. LTD.Tel: (+65) 6779 1200 Fax: (+65) 6779 1822

SlovakiaSIGMA-ALDRICH spol. s r. o. Tel: (+421) 255 571 562Fax: (+421) 255 571 564

South AfricaSIGMA-ALDRICH (PTY) LTD.Free Tel: 0800 1100 75 Free Fax: 0800 1100 79 Tel: (+27) 11 979 1188 Fax: (+27) 11 979 1119

SpainSIGMA-ALDRICH QUÍMICA, S.A. Free Tel: 900 101 376 Free Fax: 900 102 028 Tel: (+34) 91 661 99 77 Fax: (+34) 91 661 96 42

SwedenSIGMA-ALDRICH SWEDEN ABTel: (+46) 8 742 4200 Fax: (+46) 8 742 4243

SwitzerlandSIGMA-ALDRICH CHEMIE GmbH Free Tel: 0800 80 00 80 Free Fax: 0800 80 00 81 Tel: (+41) 81 755 2828 Fax: (+41) 81 755 2815

United KingdomSIGMA-ALDRICH COMPANY LTD.Free Tel: 0800 717 181 Free Fax: 0800 378 785 Tel: (+44) 1747 833 000 Fax: (+44) 1747 833 313

United StatesSIGMA-ALDRICH Toll-Free: 800 325 3010 Toll-Free Fax: 800 325 5052 Tel: (+1) 314 771 5765 Fax: (+1) 314 771 5757

VietnamSIGMA-ALDRICH PTE LTD. VN R.O.Tel: (+84) 3516 2810 Fax: (+84) 6258 4238

Internet sigma-aldrich.com

© 2003 International Union of Biochemistry and Molecular Biology www.iubmb.org

22nd Edition Designed by Donald E. Nicholson, D.Sc., The University of Leeds, England – and Sigma-Aldrich Cat. No. M3782

XXX

sigma-aldrich.com/metpath

Metabolic Pathways