2H C y c l ic P hot ph s ory l atio N n - y cli e e tr 3.5...
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 F 0 F 1 F 1 β 2 1 α β α γ 10 c-sub-u n it s A D P + P i 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- 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 3 3 β A T P ADP E N D E R GONIC R E AC TIO 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 + 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 COCH 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 (S ialate) 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-R ibos e R ibitol L-Arabitol L-Xylulose L-Ribulose L-R ibulos e-5-P L-Xylulose-5-P L-Arabinose Xylitol D-Xylose D-Arabinose D-R ibulos e ASCORBATE 2, 3-Dioxogulonate N-Ac-Glucosamine-1-P Inositol-P Inositol Glucuronate Gulonate Gulonolactone 2-Oxogulonolactone Fructose 6-P-Gluconate D-R ibulos e-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 Inos itol 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 S erine S erine Indole-3-glycerol-P 3-Deoxy-D-arabino- heptulosonate-7-P Indoleacetate (Auxin) Indoxyl Formylkynurenine K ynurenine 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-R ibosyl) 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 S hikimate-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-R ibosylformimino 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-S ulphinyl 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)CH 2OP 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 B 4 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 S phinganin 4-S phingenin 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) S qualene (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) R hodops in Metarhodopsin R etinoate trans-R etinal 11-cis -R etinol trans-R etinol (Vitamin A) R etinol 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 R ibose- 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 H C 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 H C 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 S permidine S permine 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 S emialdehyde 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 = C C O S C oA 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 B etaine B etaine 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 N RP 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-R ibos e-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 OHHO 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 O O 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 2n 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 H N 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 S edoheptulose-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 H C 3 H C 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 H C 2 C C H2 H2 - CH2 CH2 COO CH2 CH2 COO - H C 2 H C 2 CH 2 CH 2 OOC COO H N 2 N H - - CH2 H C 2 H C 2 H C 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 H C 3 HC 3 H C 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 H N 2 H C C C O CH N N C C CH N N RP HN 2 HN 2 C O O O P~ ~ P O O O O P O 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 H N 2 NH2 OOC-CH-CH COO 2 HNCO C CH N N C RP RP H N 2 OOC C CH N RP N C H N 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 R ibos e -O - P - O - P - O- Adenosine(P) + N O O O O + COO N R ibos e - O - P - O - P - O -Adenosine O O O O I I I I OH O CH CH 2 COO (NH ) 3 + E pinephrine (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 -R etinal 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-R ibulosylformimino 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 UR IDINE - 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 B ios ynthes is Degradation Amino Acids B ios ynthes is Degradation Lipids B ios ynthes is Degradation Purines & Pyrimidines B ios ynthes is Degradation B ios ynthes is Degradation Vitamins Co-enzymes & Hormones Pentose Phosphate Pathway Photosynthesis Dark Reactions COMPARTMENTATION The "Backbone" of metabolism involves GLYCOLYSIS in the CYTOPLASM, the TC A C Y C LE (mainly) in the Mitochondrial matrix and ATP FOR MATION 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 E lectron F low P roton F low Small Numbers ( eg. 2.4.6.7) refer to the IUBMBEnzyme C ommission (E C ) R eference Numbers of E nzymes LEGEND Human Metabolism is identified as far possible by black arrows B ios ynthes is Degradation HEMOGLOBIN CHLOROPHYLL ATP T R A N S L O C A T E D PROTONS 2.7.1.1 ATP 2.7.1.2 sigma-aldrich.com/pathways Argentina SIGMA-ALDRICH DE ARGENTINA, S.A. Tel: 54 11 4556 1472 Fax: 54 11 4552 1698 Australia SIGMA-ALDRICH PTY., LIMITED Free Tel: 1800 800 097 Free Fax: 1800 800 096 Tel: 612 9841 0555 Fax: 612 9841 0500 Austria SIGMA-ALDRICH HANDELS GmbH Tel: 43 1 605 81 10 Fax: 43 1 605 81 20 Belgium SIGMA-ALDRICH NV/SA. Free Tel: 0800-14747 Free Fax: 0800-14745 Tel: 03 899 13 01 Fax: 03 899 13 11 Brazil SIGMA-ALDRICH BRASIL LTDA. Tel: 55 11 3732-3100 Fax: 55 11 3733-5151 Canada SIGMA-ALDRICH CANADA LTD. 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Transcript of 2H C y c l ic P hot ph s ory l atio N n - y cli e e tr 3.5...
2H+
H+
OXA L OA C E T A T E
P Y R UV A T E
S UC C INY L -C oA
G L UT A R A T E
C IT R A T E
MA L A T E
2-OXO- A S P A R T A T E
NO2-
NO3-
N2
NH4
CH3COSCoA
A C E T Y L -C oA
HOH
C O2
NA D
TR
AN
S A MINA T IO N
2H+
2H+
+
C O2
5-A mino-levulinate
Glycine
H+H+
H+H+
H+H+
c
H+ H+a
F 0
F 1
F 1
β2
1 αβ
α
γ
10 c-s ub-units
AD P+ Pi
H+
3.6.1.34
H
+-transporting AT P synthase
α
δF 6
oscp
AT P
ADP + P i
F UMA R A T E
UQH2
UQ
UQH2
NA DH+H+
CH2COO-C(OH)COO-CH2COO-
CH(OH)COO-CHCOO-CH2COO-
-OOCCOCH2CH2COO-
-OOCCH2CH2CO.SCoA
-OOCCOCH2COO-
CH3CH(OH)CH2CO.SCoA
-OOCCH=CHCOO-
Glyoxylate Cycle
-OOCCHO
GTP
GDPATP
+
HE ME P rotoporphyrinogen C oproporphyrinogen Uroporphyrinogen P orphobilinogen
5-A mino-levulinate
COO-CH2CH2
H2NCH2C=O
F ADH2
F ADC yt.b
F e-S
S UC C INA T EII
CH3COCOO-
P Y R UV A T E
P i
X Y
C yt.c1
F e-S
2e-2e-
1e-
1e-
III
2UQ UQ
UQH22UQH2
2UQ._
UQ._
C yt.bL C yt.bH
C yt.c
IV
C uA
C uB
C uA
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
IS OC IT R A T E
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
33 β
A T P
A DP
E NDE R G ONIC R E A C TIO N
1.6
.5.3
I
F MNH2
F MN I
1.6. 5.3
2F e -S (5 C lusters )
H+ H+H+ H+
ATP
4H+
2H+
2H+or
H+
PHOTO-SYSTEM
l
O2
3.6.1.34
NADP+
GlyceraldehydeRibulose-1,5-bis-P
2β
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+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-
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+
ATPTHYLAKOID MEMBRANE
CHLOROPLAST OUTER MEMBRANE
THYLAKOID LUMEN
STROMA
(electric current)
P680Chl.a
QA
QB
Pheophytin
P700
Chl.A0
A1
Fe-S
A T P
A DP
A T P
1/2O2
H2O
PQH2
T o B rain -
AMI
NO
ACI
DS
PYRI
MI
DI
NES
PURI
NES
CATECHOLAMI
NES
AROMATI
C
AMI
NO
ACI
DS
hvV IS ION
LIPI
D
PHOTOSYNTHESIS
PORPHYRI
NS
STEROI
DS
ISOPRENOI
DS
PHOSPHOLIPI
DS
DEGRADATI
ON
LIPI
D
BI
OSYNTHESIS
PENTOSES
HEXOSES
POLYSACCHARI
DES
C O C H C H(NH )C OO2 3+
F OL ICA C ID
C 1P OOL
V A L INE
A T P
A T P
4.1.1.4 1.1.1.30
C H C OC H3 3
C H C OC H C OO3 2
C H C H(OH)C H C OO3 2
3-OH-B utyrateA c etone
A c etoac etate
K E TONE B ODIE S
HY A L UR ONIC A C ID DE R MA T A N B L OOD G R OUPS UB S T A NC E S
P E P T IDO-G LY C A N
N-A c -Neuraminate(S ialate)
UDP -Iduronate
UDP -N-A c -G alac tos amine UDP -
G alac turonate
G DP -F uc os e
T DP -R hamnos e
A DP -G luc os e
UDP -G luc os e
T DP -4-Oxo-6-deoxygluc os e
MA NNOS E
C HIT IN C HONDR OIT IN P E C T IN
A L G INA T E S
INUL IN C E L L UL OS E
O-A NT IG E NS S T A R C H G LY C OG E N
L A C TOS E
G A L A C TOS E
O
OH
HO
OH
OH
C H3 O
OP P TO
OH
OH
O
OHAC NH
HO OH
O
OHHO OP P U
NHAC
OH
OH OH
OH
HO
OH
NHC OC H
OH HO
O
OP P G
C H OH2
HO
P
UDP -N-A c -G luc os amine
pyruvateN-A c -Mannos amine-6-P UDP -G luc uronate
G DP -Mannos e
N-A c -Mannos amine UDP -N-A c -G luc os amine N-A c -G luc os amine-6-P
S orbitol
F ruc tos e-1-P
E rythros e-4-P
3-Dehydrogulonate
L -Xylos e
L -L yxos e
D-Xylulos e
D-R ibos e
R ibitol
L -A rabitol L -Xylulos e
L -R ibulos e L -R ibulos e-5-P
L -Xylulos e-5-P
L -A rabinos e Xylitol D-Xylos e
D-A rabinos e D-R ibulos e
A S C OR B A T E
2, 3-Dioxogulonate
N-A c -G luc os amine-1-P
Inos itol-PInos itolG luc uronateG ulonate
G ulonolac tone 2-Oxogulonolac tone
F ruc tos e
6-P -G luc onate
D-R ibulos e-5-P
D-Xylulos e-5-P
Mannos e-1-P
G DP -G luc os e
T DP -G luc os e
UDP -G alac tos e
G alac tos e-P
G luc os e-1-P
G luc os e-6-P
F ruc tos e-6-P
F ruc tos e-1: 6-bis -P
OH
H H HO
HOC H 2 C C C C C O
OH OHH OH
H HO
HOC H 2 C C C C O C O
OHH
H
OH H
C C
OH
C O
P -R ibos ylamine
G lyc erate2, 3-Diphos pho-
glyc erate
3-P -G lyc eraldehyde
1: 3-bis -P -G lyc erate
3-P -G lyc erate
2-P -G lyc erate
P -enolpyruvate
Inos itol
C H OH2
C H OH2
HOC H
C H OH2
C H O2
HOC H
P
G lyc erol
UDP -G alac tos eUDP -S ugars
C H C H OH3 2
E T HA NOL
Dihydroxy-ac etone-P
(G lyc erone-P )
G luc os amine-6-P
P hos pho-s erine
C hain elongation Mitoc hondrial
S erine
S erine
Indole-3-glyc erol-P
3-Deoxy-D-arabino-heptulos onate-7-P
Indoleac etate(A uxin)
Indoxyl
F ormylkynurenine K ynurenine 3-Hydroxykynurenine
3-Hydroxyanthranilate
2-A mino-3-c arboxymuc onate s emialdehyde
NH
OH
T ryptamine 1-(o-C arboxy phenylamino)1-deoxyribulos e-5-P
N-(5-P -R ibos yl)anthranilate
A nthranilate
C atec hol
NH
Indole-ac etaldehyde
NH
C H C HO2
Indolepyruvate
NH
C -C H(OH)C H(OH)C H O2 PC H
2-A minomuc onate-6-s emialdehyde
C H C H 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 2.5.1.19S hikimate-3-P S hikimate-5enolpyruvate 3-P
C horis mate
P E P
2.7.1.71
1.4.1.19
Homogentis ate P henylpyruvate
C innamate
C oumarate
P rephenate
2-A minomuc onate
F umarate A s partate
G LY C INE
S arc os ine
Hydroxy-pyruvate
P -Hydroxy-pyruvate
S E R INE
Imidazoleglyc erol-P
P -R ibos yl-A T P P -R ibos ylformimino5-aminoimidazole-c arboxamide-R P
F ormiminoglutamate
Imidazolonepropionate
Uroc anate
C ys tathionine Homoc ys teine
P hos phoadenylyl-s ulphate
(P A P S )
C H (NH )C OOH2 3
+
His tidinol-PHis tidinolHis tidinal3.1.3.15 2.6.1.91.1.1.23
3.6.1.31
5.3.1.162.4.2.17
A s paragine
A L A NINE
3-S ulphinylpyruvate
Oxobutyrate
2-A c eto-2-hydroxy-butyrate
O-P hos pho-homos erine
HO S C H C H NH2 2 2 2
HypotaurineHO S C H C H NH3 2 2 2
T aurine
G lutamate
γ-G lutamylc ys teine
G lutathione
G lyc ine
C ys teine
ß-A lanine
C ys teateS -A denos yl
homoc ys teine
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 -A denos ylmethionine
(S A M)
2-Methylac eto-ac etyl-C oA
2-A c etolac tate 2-3-Dihydroxyis ovalerate
2-Oxo-is ovalerate
3-Hydroxy-is obutyrate
3-Hydroxy-Is obutyryl-C oA
Methylac rylyl-C oA
2-Methyl-3-hydroxy-
butyryl-C oA
T iglyl-C oA 2 Methylbutyryl-C oA
2: 3-Di-OH-3-methylvalerate
2-Oxo-3-methylvalerate
Is obutyryl-C oA
C ys teines ulphinate
4.2.99.9
2-Is opropyl-malate
C H C H C OC OO3 2
+C H C H(NH )C OO3 3
C H C H(OH)C OO3
HO S C H C OC OO2 2
OC H C OC OO2P
OC H C H(NH )C OO2 3P
HOC H C OC OO2
HOC H C H(NH )C OO2 3
+
+
OH
C H C OC OO2
C OO
OH
OHO
C OO
OHOH
HO P
C OO
OHOH
O
C H2
P
C OO
O-C -C OOOH
OOH
OOC C H C OC OO2
N H
HOC -C H(OH)C H(OH)C H 2OPC H
C OO
NH2
C OO
OHNH2C OO
C OO
OC H
OOC C H NHC H2 3
C H (C H ) C OS -AC P3 2 14 C H (C H ) C OS C oA3 2 14
C H (C H ) C H=C HC O-S -AC P3 2 2
C H C H=C HC O-S -AC P3 C H C H(OH)C H C OS -AC P3 2
C OS C oA
L inoleate
Oleoyl-C oA
S tearoyl-C oA Dehydros tearoyl-C oA OH-S tearoyl-C oA Oxos tearoyl-C oA
P almitoyl-A C P P almitoyl-C oA
A C Y L -A C P 2, 3-E noyl-A C P
3, 4-Dec enoyl-A C P
2, 3-Dec enoyl-A C P
3-OH-A c yl-A C P 3-Oxoac yl-A C P
3-Oxo-Dec anoyl-A C P
3-Oxo-Hexanoyl-A C P3-OH-Hexanoyl-A C P2, 3-Hexenoyl-A C P
B utanoyl-A C P C rotonoyl-A C P 3-OH-B utanoyl-A C P A c etoac etyl-A C P
Hexanoyl-A C P
3-OH-Dec anoyl-A C PDec anoyl-A C P
P almitoleoyl-A C P
γ-L inolenate A rac hidonate L eukotriene B 4
C OS C oA
C O-S -AC P
T hromboxane B 2
HOOC C H C O-S -AC P2
Malonyl-A C P
HOOC C H C O-S C oA2
Malonyl-C o-A
C H C O-S -AC P3
A c etyl-A C P
C H O-C O-R2
C H OH2
R ’-C O-OC H
F A T T Y A C IDA C Y L -C oA
(C ytos ol)
C H O-C O-R2
C H O2
R ’-C O-OC H
P
C ardiolipin P hos phatidylglyc erol
A c etylc holineG lyc erophos phoc holine
L ys olec ithin
C holineplas malogen
C DP -c holine C holine-P
Mevaldate
C H (C H ) C H=C HC H(OH)C HC H OH3 2 12 2
Dehydros phinganin S phinganin 4-S phingenin P s yc hos ine
A c yl-C oAA c yl-C oA
C erebros ideG alac tos eC H (C H ) C H=C HC H(OH)C HC H O-3 2 12 2
NHC OR
Is opentenyl-P P(C 5)
Dimethylallyl-P P(C 5)
G eranyl-geranyl-P P(C 20)
F arnes yl-P P(C 15)
S qualene(C 30)
G eranyl-P P(C 10)
Des mos terol Zymos terol L anos terol
C H C = C HC H O3 2 P P
C H3
C eramide
G anglios ides
NHC OR
C H O2 P P
O P P
C H2
C HOL E S T E R OL
C H C (OH)C H C H OH3 2 2
C H C OO2
C H C (OH)C H C HO3 2
C H C OO2
NADP +Dehydroas c orbate
OH
H O
HOC H 2 C C C C C O
OHH OH
OH
H O
HOC H2 C C C O C O C O
H
NA D+P i
A DPA DP
P hytoene(C 40)
L yc opene (C 40)
ß-C A R OT E NE (C 40)
R hodops inMetarhodops in
R etinoate
trans -R etinal
11-c is -R etinoltrans -R etinol(V itamin A )
R etinol es ters
Dark
L ight
Ubiquinone(C oenzyme Q)
Menaquinone
P las toquinone
P hylloquinone(V itamin K )
Ops in
C HO
C H OH2
C HO
C H OH2
C H3C H O3
C H O3 n
O
O
O
O
P hytol (C 20)
α-T oc opherol(V itamin E )
Quinolinate
Quinolinate-nuc leotide
Nic otinate-nuc leotide
Des amino-NA D
5-Hydroxy-tryptophan
5-Hydroxytryptamine(S E R OTONIN)
N-A c etyl-5-O-methyl-s erotonin(ME L A TONIN)
NH
C H C H NHC OC H2 2 3HO
NH
C H C H NHC OC H2 2 3C H O3
+NA D( P )
NIC OT INA T E
N-A c etyl-s erotonin
2.4.2.19
Dopamine Dopa
Dopaquinone
T HY R OXINEME L A NIN
OH
OH
C HOHC H NHC H2 3
OHOH
C HOHC H NH2 2
4-OH-3-Methoxy-phenylglyc ol
C HOHC H NH2 2
OHOC H 3OC H 3
C HOHC H OH2
OH
OC H 3
4-OH-3-Methoxy-D-mandelate
C yc lic A MPA T P
Dephos pho-C oenzyme A
4-P -P antetheine
4-P -P antothenylc ys teine
4-P -P antothenate
P antoate
6.3.2.1
1.1.1.169
3.5.1.22
2.7.1.33
NH
NH
O
O
O
O
C H OH2
OH
OC H 3
C H(OH)C OO
H2
NH3
+C H-C OO
CO
O
C OO
NR ibose- PN+
C OO
NH
C H C OO2
O
OH
C H O2 P
NHC OC H NH2 2
OH
F ormylglyc inamide-R P
Urea
F ormylglyc inamidine-R P
A llantoate A llantoin UR A T E
A DP
Xanthine Hypoxanthine
Inos ine
A denine
A denylo-s uc c inate
5-A minoimidazole-R P
5-A mino-4-imidazolec arboxylate-R P
5-A mino-4-imidazole(N-s uc c inylc arboxamide)-R P
5-A minoimidazolec arboxamide-R P
F ormylamido-imidazole-
c arboxamide-R P
H NC ONH2 2
HNH C2 C HO
NHR P
NH
C
CCO
CC O
OCNH
N H
HN
HN
H
CCO
CC H
OCNH
N
N
HN
C arbamoylß-alanine
Dihydro-urac il Urac il
d-A DP
d-A T P
G T P G DP
XA NT HOS INE -P(XMP )
T T P
T DP
ß-Ureidois obutyrate
Dihydrothymine
T hymine d-UMP d-C MP d-C DP
C DP
C arbamoylas partate
Dihydroorotate
Orotate Orotidine-P Uridine-P(UMP )
UDP
3-A mino-is obutyrate
C HCNH 2
C HOCNH
NC HCO
C HOCN H
HN
C H-C H3CO
OCN H
HN
C H 2
C H2
C H2
CO
OCNH
HN
CO
C HOCN H
HN C C H3
Methylmalonyls emialdehyde
OHC C HC OO
C H3
C H2CO
C H-C OOOCN H
HN C HCO
C -C OOOCN H
HN
H NC ONHC H C H C OO2 2 2
CC
CC H
R PHC
NH
NH
OOC -C H-C H C OO2
N
N
N
C HO
NHR P
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
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
1.3.1.10
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 -C OOH
Oxalate
G lyc olate
HOC H C HO2
G lyc olaldehyde
E thanolamine-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
3.1.4.3
3.1.4.4
2.7.7.15
3.1.1.5 3.1.4.2
2.7.1.32
2.7.1.82
1.2.4.12.3.1.121.8.1.4
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
6.3.5.1
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 1.1.3.221.1.3.22
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
A C E T A T E
2.4.2.4
2.1.1.45
R P
C HCO
C HOC 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
4.1.1.296.3.2.3
6.3.2.2
1.8.1.3
L A C T A T E
A c etaldehyde
2.7.1.24
2.7.7.3
4.1.1.36
B ile A c ids
C H C H C OS C oA3 2
P ropanoyl-C oA
1.1.1.31
2.1.3.14.1.1.415.1.99.1
6.4.1.3
6.3.2.5
2.1.1.14
2.1.1.13
4.6.1.1
C DP -E thanolamine
1.1.1.35 4.2.1.17
+HO S C H C H(NH )C OO2 2 3
3.5.2.7NHHN
C H
OOC C HC H C H C OO2 2
C MP -N-A c etylneuraminate
C DP -diac ylglyc erol
C HOL INE
E thanolamine
G lyoxylate
HIS T A MINE
2.3.1.46Homos erine
T yramine
P lant P igmentsT annins
Maleylac etoac etate
F umarylac etoac etate
5.2.1.2
C H C OO2
OH
OH
OH
C H C H NH2 2 2
OH
OH
C H C H NH2 2 2
Hydroxyphenylpyruvate
α-T oc opherol(V itamin E )
L IG NIN
d-G T P
OH
OH OH
O
HO
OH
P
OP P T
C H3HO
OHOH
O
NA DP H
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
A T P
C H C H 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 C H C H O2 P
H HC OO
NH2
C OO
6.3.5.3 6.3.2.6 4.3.2.2
G uanineDNA
6.3.4.44.3.2.2
CCO
CC H
HCNH
N
N
HN CCO
CC H
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
Diphos pho-mevalonate
Mevalonate
3-Oxopentanoyl-C oA
3-Oxoac yl-C oA3-OH-A c yl-C oA2, 3-E noyl-C oA
2, 3-Hexenoyl-C oA 3-OH-Hexanoyl-C oA
A c etoac etyl-C oA3-OH-B utanoyl-C oAC rotonoyl-C oA
P entanoyl-C oA 3-OH-P entanoyl-C oA
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 F atty ac ids
S uc c inylhomos erine
C O 2
2-OXO A C ID
G lutamyl-P
G lutamine
UR E A
P -C reatineC reatine C reatinine
G lyc ine
C IT R UL L INE
G lutamic s emialdehyde
2-A MINO A C ID
P yrroline-5-c arboxylate
G lyoxylateP yruvate
4-Hydroxy-2-oxoglutarate
4-Hydroxy-glutamate
3-Hydroxy-pyrroline-
5-c arboxylate
P utres c ineH NC H C H C H C H NH2 2 2 2 2 2
S permidine
S permine
N -T rimethyllys ine66N -T rimethyl-3-OH-lys ine
C arnitine
G lutaryl-C oA S ac c haropine2-A minoadipates emialdehyde
2-A minoadipate2-Oxoadipate
A rginino-s uc c inate
G uanidoac etate
Methylmalonyl-C oA
4.1.2.12
A s partylS emialdehyde
2, 3-Dihydro-dipic olinate
1.2.1.11
4.2.1.52 1.3.1.26 P iperideine-2, 6-dic arboxylate
N-S uc c inyl-2-amino-6-oxo-
pimelate
2.6.1.17N-S uc c inyl-2, 6diaminopimelate
Diamino-pimelate
3.5.1.18
3-Methyl-glutac onyl-C oA
(C H ) C HC H C OS C oA3 2 2(C H ) C HC H C OS C oA3 2 2
3-Methyl-c rotonyl-C oA
Is ovaleryl-C oA
OxopantoateHC HO
OOC C H C = C HC OS C oA2
C H3
C H C OC HC OS C oA3
C H3
C H C H=C HC OS C oA3
C H3C H C H(OH)C HC OS C oA3
C H 3
C (OH)C H(OH)C OO
C H C H3 2
C H3
C H = C C OS C oA2
C H3
HOC H C HC OS -C oA-2
C H3
C H C HC O-S C oA3
C H3
C (OH)C H(OH)C OO
C H3
C H3
C H C H C HC OS C oA3 2
C H 3
C H C = C HC OS C oA3
C H3
A T P
4-A minobutyrate(G A B A )
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
1.1.1.85Oxoleuc ine
C OOH
(C H ) C HC HC H(OH)C OO3 2
S -A denos ylmethylthiopropylamine
(Dec arboxylated S A M)
P R OL INE
C oenzyme A
C H C = C HC H3 2
C H 3
OC H
C H
3
3HO
C H3C H3
C H 3
C H C -C H H O3 2 2C P P
C H2
C H C = C HC H O2 2 P P
C H3
3-P -G lyc erol
P hos phatidylethanolamine
C E P HA L IN
3.1.4.12
2.7.8.3
P roges terone
1.5.1.12
2.7.3.2
4.2.1.173.1.2.4
2.6.1.32
4.4.1.15
A c etyls erine 2.7.7.42.7.1.251.8.99.1A denylyls ulphate
(A P S )
2.7.1.39
4.4.1.15
4.1.1.29
4.2.99.8
2.3.1.30
P -R ibos yl-P P
1.1.1.1
1.2.1.4
A s partyl-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
C HOL INE
2.1.1.13
1.3.1.2
NHC H C H S H2 2 NHC H C H C O2 2OC H C (C H ) C H(OH)C O2 3 2P
ADP - NHC H C H S H2 2 NHC H C H C O2 2OC H C (C H ) C H(OH)C O2 3 2
P -ADP - NHC H C H S H2 2 NHC H C H C O2 2OC H C (C H ) C H(OH)C O2 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
+C H C O-OC H C H(NH )C OO2 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
G lyoxylate
2.1.1.6
1.4.3.4
1.14.18.1
1.14.16.2
Hexanoyl-C oA
B utanoyl-C oA
6.3.4.166.3.5.5
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
S O -42
1.14.16.4
NH 2 OOC OOC
4.1.1.25
1.3.1.13
1.3.1.13
2.7.4.6
C Y T IDINE -triphos phate
(C T P )
C ytos ine
2.4.2.9
4.1.1.11
2.6.1.18
4.3.1.3
4.2.1.49
3HS O -
1.1.1.105
2.3.1.41
NA DP H
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
OP P U
C H OH2
C H OH2
HO OH
OH
HO
2.4.1.21
4.2.1.52
1.2.1.18
4.2.1.18
O
C HC
C HOCN
HN
DP
C HCO
C HOCN
HN
R P P P
OC H 2
H
C C
H
OHOH
C H
NHNCH
CP
H
O
OC H2 C C
H
OH
H
OH
C
H
C CC
NH2
CC H
HCN
R P (P P )
N
N
N+
P
NH2H
O
OC H 2 C C
H
OH
H
OH
C
H
C COC
CC H
HCN
R P
N
N
NHP
H
OC H 2 C C
H
OHOH
C O C H2 C
C ONH 2
CC H
HCN
R P
N
N
NHP
+OOC C H N(C H )2 3 3
B etaine
B etainealdehyde
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
C H 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-C oA
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
CC H
OCN R P
N
NH
HN
CCO
CC H
N
N
N
HN
R PH N2 C
2.7.4.6
1.17.4.1
2.7.4.6
2.6.1.13
C arbamoyl-P
2.3.1.9
C arnitine
2.6.1.4 2.6.1.44
C H C (OH)C H C OS C oA3 2
C H C OO2
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
C arnos ine
C H C H NH2 2 2C
NHNC
HC
H
4.1.1.22
4.3.1.3
Ubiquinone
P las toquinone
D-R ibos e-5-P
NH
C H C H(NH )C OO2 3HO+
O
OH
OH
HO
OP P U
C OO -
O
OH
OH
HO OP P U
C OO -
OH
H OH
HOC H 2 C C C O
H
C O C OO -
OC HOH
C HOHAcNH
HO
OP C
OC O -C H OH2
OC HOHC HOHAcNH
HO
OH
C OOC H OH2
O
OHOH HOHO
C H O2 P
O
OHAC NH
HO OH
C H O2 P
O
OOH HOHO P
C H OH2
O
OHOH HOHO
C H OH2
O
OHHO OH
3
C H O2 PO
OHHO O
NHC OC H 3
P
C H OH2C H OH2C H OH2
O
OHHO OH
NH2
C H O2 P
O
OH
HO
OH
OP P U
C H OH2
O
O
HO
OH
OH
HO
P
C H OH2
C H OH2O
OHO
OH
OH
O
OHOH
OH
C H OH2
O
OHHO
OH
OH
C H2C H OP2
OH
H H HOH
C C C C
OH OHH
C OO -HOC H 2
H
OH OHOH
C C C C HO
HH
HOC H 2
H
OH OHH
C C C C HO
HOH
HOC H 2
OH
H OHH
C C C C HO
HOH
HOC H 2
H
OH HOH
C C C C HO
OHH
HOC H 2
OH
H HOH
C C C C HO
OHH
HOC H 2
OH
H OHOH
C C C C HO
HH
HOC H 2
H
OH HOH
C C C C
OHH H
OH
C OO -P OC H2
OH
H OH
C C C O
H
P OC H2 C H OH2
H
OH H
C C C O
OH
HOC H 2 C H OH2
C H OH2P OC H 2
H
OH OH
C C C O
H
C H OH2P OC H2
OH
H H
C C C O
OH
C H OH2P OC H2
H
OH OH
C C C O
H
HOC H 2 C H OH2
OH
H OH
C C C O
H
HOC H 2C H OH2
OH
H H
C C C O
OH
HOC H 2 C H OH2
H
OH OHH
C C C
HOH
HOC H 2 C H OH2
OH
H OHOH
C C C
HH
HOC H 2C H OH2
H
OH HOH
C C C C
OHH H
OH
C H OH2HOC H 2
H
OH OH
C C C HO
H
P OC H 2
H
OH HOH
C C C C O
OHH
HOC H 2C H O2 P
H
OH OHOH
C C C
HH
HOC H 2 C H OH2
H
OH OH
C C C
H
C O
H
HO
P OC H2C H OH2
P
H
OH OH
C C C
H
C O
H
HO
C H O2 POC H 2
H
OH OH
C C
H
C C HO
OH
H
P OC H 2P OC H 2
O
OH
NH2
OH
C H O2 P
C HOHC HOP OC H 2
HOC H2C OC H2OP
O
OH
O OP P
OH
C H O2 P
C HOHC OO PP OC H 2
C HOHP OC H2 C OO
C OO
OH
OHOOH
C OO
C H (C H ) C H(OH)C H C OS -C oA3 2 14 2C H (C H ) C H(OH)C H C OS3 2 14 2
C H (C H ) C OC H C OS -C oA3 2 14 2
C H (C H ) C OC H C OS -C oA3 2 14 2
C H (C H ) C OS -C oA3 2 n+2
C H (C H ) C H=C HC OS -C oA3 2 14
C H (C H )3 2 nC H=C HC OS -C oA
C H (C H )3 2 5 2C H=C HC H C OS AC P
C H (C H )3 2 6C H=C HC OS AC P
C H (C H )3 2 6C OC H C OS AC P2C H (C H )3 2 6 2 2C H C H C OS AC P
C H (C H )3 2 2 2 2C H C H C OS AC P
C H C H C H C OS AC P3 2 2
C H (C H )3 2 6C H(OH)C H C OS AC P2
C H C H=C HC O.S -AC P3
C H (C H )3 2 2 2C OC H C OS AC P
C H3C OC H C OS AC P2
C H (C H )3 2 n 2C OC H C OS AC PC H (C H )3 2 n 2C H(OH)C H C OS AC P
C H (C H )3 2 2 2C H(OH)C H C OS AC P
A C Y L -C oA(Mitoc hondria)
C H (C H ) C H C H C OS C oA3 2 2 2n
C H (C H ) C H=C HC OS C oA3 2 n C H (C H C H(OH)C H C OS C oA3 2n
C H (C H ) C H C H C OS C oA3 2 2 2 2 C H (C H ) C H=C HC OS C oA3 2 2
C H (C H ) C OC H C OS C oA3 2 2n
C H C OC H C OS C oA3 2
C H (C H ) C H(OH)C H C OS C oA3 2 2 2
C H C H(OH)C H C OS C oA3 2C H C H=C HC OS C oA3C H C H C H C OS C oA3 2 2
C H C H C H C H C OS C oA3 2 2 2
P entenoyl-C oAC H C H C H=C HC OS C oA3 2 C H C H C H(OH)C H C OS C oA3 2 2
C H (C H ) C OC H C OS C oA3 2 2 2
C H C H C OC H C OS C oA3 2 2
OH OH
HO OH
O
O-C H O-P O2
C H C HOHC H OH2 2
O
C H2
C H2
R '-C O-OC H
O-C O-R
O-P O
O-
HOC H C H2 2NH 3
+P OC H C H2 2NH3
+C P P - OC H C H2 2 NH3
+
O
-
C H O-C O-R2
C H O P2 OC H C H2 2NH 3
+
C H C OC H C H N(C H )3 2 2 3 3
HOC H C H N(C H )2 2 3 3
+
C H C H 2 C OO(NH )3
+
OHOH
C H C H 2 C OO- (NH )3
+
C O
NH2
C H C H(NH )C OO2 3+
NHOC
C O
NHOC
NH
CH
H N2
HCC H
N
N
C
R PH N2
C HC
C HOCN
N
DP
NH2
R P P P
C HC
C HOCN
N
NH 2
CC
CC H
R P (P )HC
N
N
N
N
NH2
H NC OO2 P
(C H ) NH2 3 2H N(C H ) NH2 2 3 (C H ) NH2 4
(C H ) NH2 3 2H N(C H ) NH2 2 4
C H -S C H C H C HNH3 2 2 2
A denos yl
+
+C H3
C H3
C HC H(NH )C OO3
++C
NHNC
HC
H
C H C H(NH )C H OH2 3 2
+C
NHNC
HC
H
C H C H(NH )C H OP2 3 2C
NHNCH
HC C H C OC H OP2 2
+HS C H C H C H(NH )C OO2 2 3
+
+S C H C H C H(NH )C OO2 2 3
C H C H(NH )C OO2 3
R P
CO
C -C OOOCN
HN C H
2.4.1.23
C H (C H ) C H=C HC H(OH)C HC H OH3 2 12 2
NH 3
+
C H (C H ) C H(OH)C HC H OH3 2 14 2
NH 3
+
C H (C H ) C OC HC H OH3 2 14 2
NH 3
+
G alac tos eC H (C H ) C H=C HC H(OH)C HC H O-3 2 12 2
NH 3+
4.1.1.70
H NC ONH2 2
OHC C H N(C H )2 3 3
+
C -C H3CO
C HOCN DP
HN
DP
C P P -O C H C H N(C H )2 2 3 3
+OC H C H N(C H )2 2 3 3
+
1.2.1.41
UDP -N-A c -Muramate
O
O
C H C H3
C OO-
NHAC
HO OP P U
C H OH2
4.1.3.20
O
OH
C H3
HO HO OP P G
2.7.7.24
2.4.1.22
2.7.7.12
5.1.3.2
5.3.1.4
S edoheptulos e-P P
3.1.1.28
4.2.1.24
N
C H2
C H2
N
N
N
C H3
C H3
C H
C H
C OO
C HC H
C H2
H C3
H C3H C3
HC
C
C
H
H
F e
C H2
C H2
C OO - -
C H3
C H3
C H2
C H2
C H2
H C3
H C3N
H
NH
NH
NH
C H
C H
H C2
C
CH2
H2
-
C H2
C H2
C OO
C H2
C H2
C OO -
H C2
H C2
C H 2
C H 2
OOC
C OO
H N2
NH
-
-
C H2
H C2
H C2
H C2
H2
H2
C H2
C H2 C H2
C H2
C H2
C H2
NH
NH
NH
NH
C OO
C OO
C OOC OO
C
C
-
-
C H2
C H2
C OO
C H2
C H2
C OO- -
-
-
OOC-
OOC-
C H3
C H3
H C3
H C3
H C2
H2
H2
NH
NH
NH
NH
C H2
C H2
C H2
C H2
C H2
C
C
C OO-
C H2
C H2
C OO
C H2
C H2
C OO- -
C OO-
C OO-
C H C (OH)C H C H O3 2 2 P P
C H C OO2
OHC C OO
HOC H C OO2
NH2
H NC NHC H C OO2 2
+ NH2
H NC N(C H )C H C OO2 3 2
+ NH2
HNC N(C H )C H C OO3 2P -
+ HN CNH C O
N C H 2
C H3
OOC C HC H C OO2
H NC NHC H C H C H C H2 2 2 2
N
(NH )3
+C OO
C HC OOHC
C H2HOC H
N
OOC C H(OH)C H C H(NH )C OO2 3
+
C HC OO
C H2HOC H
H C2NH
NH
C HC OO
C H2C H2
C H2
OOC C H(OH)C H C OC OO2
N
C HC OO
C H2C H2
C H
C H C OC OO3 OHC C OO
+H NC ONHC H C H C H C H2 2 2 2 (NH )3 C OO
H NOC C H C H C H2 2 2 C OO(NH )3
+
R -C O-C OO
+
C OOR -C H(NH )3
+
C OOH NOC C H C H2 2 (NH 3
+
OOC -C H-C OS C oA
C H3
P OOC C H C H2 C OO(NH )3
+
OOC C H C H C HO2 2
OHC C H C H2 C OO(NH )3
+
(C H ) NC H C H(OH)C H C OO3 3 2 2
+
OHC C H C H C H2 2
+C OO(NH )3
P OOC C H C H C H2 2
+C OO(NH )3
OHC C H C H C H C H2 2 2 C OO(NH )3
+NH C HC H C H C OO2 2
C OO
C H C H C H C H C H2 2 2 2 C OO(NH )3
+
H N(C H )2 42 C H(NH )C OO3C H(NH 3++
(C H ) N(C H )3 3 2 3 C H C H(NH )C OO2 3
+ +
C H 2CH
OOC CN
HC
C H-C OO
C H2CH2
C H-C OO OOC CN
H C2
OOC C OC H C H C H C H-C OO2 2 2C H C H2 2 2
OOC C H C H C ONH2 2 OOC C HC H C H C H C H-C OO2 2 2
OOC C H C H C ONH2 2C H2 2
NH3
+OOC C H-C H C H C H C HC OO2 2 2
NH 3
+
NH3
+
(C H ) C HC (OH)C H3 2 2
C OOH
C OO (C H ) C HC H C OC OO3 2 2
+(C H ) C HC H3 2 2 C H(NH )C OO3
HOC H C HC OO2
C H3
C HC OC OO
C H3
C H3C H C OC (OH)C H3 3
C OO
+P OC H C H C H(NH )C OO2 2 3
+HOC H C H C H(NH )C OO2 2 3
+C H C H C H(NH )C OO2 2 3 OOC C H C H2C OO 2
+C H S H2
OOC C H(NH )C H C H C ONHC HC ONHC H C OO3 2 2 2
HOC H C (C H ) C OC OO2 3 2
HOC H C (C H ) C H(OH)C OO2 3 2
NHC H C H C OO2 2HOC H C (C H ) C H(OH)C O3 2)2 3 2
NHC H C H C OO2 2OC H C (C H ) C H(OH)C O2 3 2P
C H C H3 2
C H 3
C H+
C H(NH )C OO3
C H C OC (OH)C H C H3 2 3
C OO C HC OC OO
C H C H3 2
C H3
NHC HC H S H2
C OO
NHC H C H C O2 2OC H C (C H ) C H(OH)C O2 3 2P
+C H S H2
OOC C H(NH )C H C H C ONHC HC OO3 2 2
+AdenosylS C H C H C H(NH )C OO2 2 3
+S C H C H C H(NH )C OO2 2 3
+HO S C H C H(NH )C OO3 2 3
+
+S -C H C H(NH )C OO2 3
S -C H C H(NH )C OO2 3+
HS C H C H(NH )C OO2 3
1.1.1.23
H
C
NHNC
HC C H C HC OO2
NHC OC H C H NH2 2 2
+
H
C
NHNC
HC C H C H(NH )C OO2 3
C HC H C H C OO2 2
NHNC H
O C C C H C HC OO
NHNC H
C H
C H C OO3
NH
OOC
C H-C OOOC
NH2 C H2
H NC H C H C OO2 2 2
H NC H2 2
C H3C HC OO H NC ONHC H C HC OO2 2
C H3
CCO
C H
R PHC N
N
N
HN
C
CCO
C HHC O
N
N
N R P
CC H
N
NH N2
HC
CCO
C H
N
NC
CC H
N
N
R P
H N2
H N2C
O
O
O P~ ~P O
O
O O
P O
O
C H2
N
N
N
N
O
OHOH
NH2
HCC HN
N
N
N O
O
P O O
O
C H2
OH
NH2
HCC H
C OOC O
NHOC
NH
CH
H N2NH2
OOC -C H-C H C OO2
HNC O CC H
N
N
C
R PR PH N2
OOCC
C H
NR P
N
CH N2
C H=C HC OO
OH
C H=C HC OO
C H C OC OO2
C H2
P
C OO
OHO
O
O
C OO
O
C H C OO2O
C H C OO2-OOC
OC H 2 C H2
OHHC
P
HOC H HC OH
OCC OO
C OOHO
OHOHO
NH2C OOOC H
NH
C H C OC OO2NH
C HO
C O
NH2OH
C H C H(NH )C OO2 3
+
N
C OO
C OO
N+
C OO
C OO
R P
O
OH
OH
HO OP P U
C OO
O
OH
NHC OC H 3
HO
OP P U
C OOC H OH2
O
OCC H
2 NHAC
HO OP P U
C OO
C H OH2
O
OHHO OH
OH
C OO
OOC C H N(C H )2 3 2
Dimethylglyc ine
1.1.99.1
1.2.1.8
C OOHO HO
C OO
O
HO OH
C OO
C H(O ) PP OC H2 C OO C H(OH)HOC H2 C OOC OO
C H(O )PHOC H2 C OO
C H =C (O )2 P C OO
C ONH 2
R ibose -O - P - O - P - O- Adenosine(P )
+N
O
O
O
O
+
C OO
NR ibose - O - P - O - P - O -Adenosine
O
O
O
O
II
IIOH
O
C H C H 2 C OO(NH )3
+E pinephrine
(A drenaline)Norepinephrine
(Noradrenaline)
Normetepinephrine(Normetadrenaline)
HOC H C H N (C H )2 2 3 3
+
Adenosyl+
+S C H C H C H(NH )C OO2 2 3
C H 3
(C H ) N(C H )3 3 2 3 C H C H(NH )C OO2 3
+ +OH
OOC C H C H C H C OS C oA2 2 2
OOC C H C H C H NH2 2 2 2
OOC C H C H C H C OC OO2 2 2 OOC C H C H C H C H2 2 2 C OOC OO(NH )3
++
HOH
HOH
HHO
HHO
H
P ros taglandin P G E2
OH
HOC H 2 C C C O C C OO
OHH
OHH H
-
C OO
OR '-C O-OC H
C H O-C O-R2
C H O P OC MP2
O
C H C H N(C H )2 2 3
+OHOC H
C H OP O2
C H OH2
O-
C H OP O2
O
C H OC H=C HR2
C H C H N(C H )2 2 3 3
+
O-C H OP O2
OR '-C O-OC H
C H O-C O-R23.1.1.32
C H C H N(C H )2 2 3 3
+
O-
OHOC H
C H OP O2
C H O-C O-R2
C H C H N(C H )2 2 3 3
+
O-
C H C H(NH )C OO2 3+
+C
NHNC
HC
H
C H C H(NH )C HO2 3
HS
11-c is -R etinal
P i
A DP
NADP +
G DP -Mannuronate
Mannos e-6-PDehydro-s hikimate
S hikimate
R NA
d-G DP
d-C T P
G UA NOS INE -P(G MP )
ß-A lanine
P -R ibos yl-A MP P -R ibulos ylformimino5-aminoimidazole-c arboxamide-R P
Imidazoleac etol-P
HS HS O -
P A NTOT HE NA T E
3-Is opropyl-malate
S uc c inics emialdehyde
2.4.1.17
Diac ylglyc erol
2.3.1.6
1.14.12.1
1.4.4.2
C H C HO3
3.5.4.19
4.2.1.19
3.3.1.1
4.1.1.12
4.1.2.5
C OO-2OHC C H
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
A DP
P -G luc onolac tone
1.1.1.44
O
OOHHO
OH
C H O2 P
P HE NY L A L A NINET Y R OS INE
T R Y P TOP HA N
INOS INE -P(IMP )
T HY MIDINE -P
HIS T IDINE
UR IDINE -triphos phate
(UT P )
C Y S T INE C Y S T E INE
IS OL E UC INE
L E UC INE
LY S INE
OR NIT HINE
A R G ININEHY DR OXYP R OL INE
P HOS P HA T IDY LS E R INE P hos phatidyl
inos itol
L E C IT HIN
S P HING OMY E L IN
S T E R OIDS
P regnenolone
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
C O
OH
C
H
H
OH
P OC H2 C H O2 P
5.4.2.1
A DP
4.2.1.11
E ndoplas mic R etic ulum
1.1.1.100
3.1.1.3
P hos phatidate
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
P O
O
C H (C H ) C H=C HC H(OH)C HC H O3 2 12 2
NHAcyl
C H C H N(C H )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
ME T HIONINE
4.1.3.27
4.2.1.51
1.14.17.1
1.14.18.1
1.14.13.11
G lyc inamide-ribos yl-P
4.2.1.22
3-Oxohexanoyl-C oA
T HR E ONINE
1.2.1.25
1.2.1.25
1.2.1.25
1.5.1.7 - 10
G L UT A MA T E
2.3.1.38
A T P
NA DH
S UC R OS E
A DE NOS INE -P(A MP )
T riac ylglyc erolF A T
R NA
C H 3
C H2
OC -C OOOH
C OO
C H C H 2 C OO(NH )3
+
G LY C OP R OT E INSG A NG L IOS IDE S
MUC INS
4.1.2.-
2.6.1.-
G L UC OS E
O-A c yl-c arnitine
O-A c yl-c arnitine
OH
O-
-
R -C O-OC H
R '-C O-OC H
R '-C O-OC H
O HC O-C O-R
C H C H(OH)C H O-P -OC H2 2 2
C H O-C O-R ’2
OR '-C O-OC H
O -
C H O-C O-R2
C H O-P O2O-
2.7.8.11
H NC H C H C H C H2 2 2 2 C OO(NH )3
+
2.3.1.20 3.1.3.4 2.7.1.107
NH2
+
+H NC NHC H C H C H C H2 2 2 2 C OO(NH )3
H
OH HOH
C C C C O
OHH
HOC H 2C H OH2
R -C H2C OO
C H O-C O-R2
C H O-C O-R "2
R ’-C O-OC H
OH
O
C H C HNH2 3+
OR '-C O-OC H
O-
C H O-C O-R2
C H O P O2
C OO
OOC C H C H C H2 2 C OO(NH )3
+C H C H(OH)C H(NH )C OO3 3
O
OHHO
OH
OH
C H OH2C H OH2
NH
C H O-C O-R2
1.3.1.13
4.1.1.28
Malonics emi-
aldehyde
2.7.2.4
2.1.3.3
3.5.1.26.3.1.2
6.3.5.
5
C arbohydratesB iosynthes is
Degradation
A mino A c idsB iosynthes is
Degradation
L ipidsB iosynthes is
Degradation
P urines &P yrimidines
B iosynthes is
Degradation
B iosynthes is DegradationV itamins C o-enzymes & Hormones
P entos e P hos phate P athway
P hotos ynthes is Dark R eac tions
C OMP A R T ME NT A T IONT he "B ackbone" of metabolism involves
G LY C OLY S IS in the C Y T OP LAS M,
the T C A C Y C LE (mainly) in the Mitochondrial matrix
and AT P F OR MAT ION spanning the
MIT OC HONDR IAL INNE R ME MB R ANE
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
E lectron F low P roton F low
S mall Numbers ( eg. 2.4.6.7) refer to the IUB MB E nzyme
C ommiss ion (E C ) R eference Numbers of E nzymes
L E G E ND
Human Metabolism is identified as far poss ible by black arrows
B iosynthes is Degradation
HE MOG L OB IN C HL OR OP HY L L
A T P
TR
AN
SL
OC
AT E D P R OTONS
2.7.1.1
A T P2.7.1.2
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