Upload File

sigma metabolic pathways

1
sigma-aldrich.com/pathways 2H+ H+ OXALOACETATE PYRUVATE SUCCINYL-CoA GLUTARATE CITRATE MALATE 2-OXO- ASPARTATE NO2 - NO3 - N2 NH4 CH3COSCoA ACETYL-CoA HOH CO2 NAD T R A N S A M IN A TIO N 2H+ 2H + + CO2 5-Amino- levulinate Glycine H+ H+ H+ H+ H+ H+ c H+ H+ F0 1 F1 β 2 1 α β γ 0c-sub-unit s A D P + P i 3.6.1.34 H + -transporting AT P synth a s e α δ F6 oscp ATP ADP + Pi FUMARATE UQH2 UQ UQH2 NADH+H + CH2COO- C(OH)COO- CH2COO- CH(OH)COO- - 2COO- -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.bL Cyt.bH Cyt.c IV Cu A Cu B Cu A 1.9.3.1 2e- Heme a Heme a3 2H+ 2H+ 4H+ 4H+ 2H+ NAD+ NADH+H+ NAD+ 1.1.1.39 1.2.4.1 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 NDERGONICREACTIO 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 ε a α 1 α ε α β 2 1 3 α α β 3 α 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 N on-cyclic electro n flo w 2e- 2e- Mn 2e- * Protons from Water H2O H+ H+ 2H+ 2H+ γ CO 2 Fixation H+ ADP Pi H+ NADPH+H+ ATP THYLAKOID MEMBRANE CHLOROPLAST OUTER MEMBRANE THYLAKOID LUMEN STROMA (electriccurrent) 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 P OCH CH(NH )COO 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 NH HOC-CH(OH)CH(OH)CH2OP CH COO NH2 COO OH 2 COO COO OCH OOCCH NHCH 2 3 CH (CH ) COS-ACP 3 2 14 CH (CH ) COSCoA 3 2 14 CH (CH ) CH=CHCO-S-ACP 3 22 CH CH=CHCO-S-ACP 3 CH CH(OH)CH COS-ACP 3 2 COSCoA Linoleate Oleoyl-CoA Stearoyl-CoA Dehydrostearoyl-CoA OH-Stearoyl-CoA Oxostearoyl-CoA Palmitoyl-ACP Palmitoyl-CoA ACYL-ACP 2, 3-Enoyl-ACP 3, 4-Decenoyl-ACP 2, 3-Decenoyl-ACP 3-OH-Acyl-ACP 3-Oxoacyl-ACP 3-Oxo-Decanoyl-ACP 3-Oxo-Hexanoyl-ACP 3-OH-Hexanoyl-ACP 2, 3-Hexenoyl-ACP Butanoyl-ACP Crotonoyl-ACP 3-OH-Butanoyl-ACP Acetoacetyl-ACP Hexanoyl-ACP 3-OH-Decanoyl-ACP Decanoyl-ACP Palmitoleoyl-ACP γ-Linolenate Arachidonate Leukotriene B4 COSCoA CO-S-ACP Thromboxane B2 HOOCCH CO-S-ACP 2 Malonyl-ACP HOOCCH CO-SCoA 2 Malonyl-Co-A CH CO-S-ACP 3 Acetyl-ACP CH O-CO-R 2 CH OH 2 R’-CO-OCH FATTY ACID ACYL-CoA (Cytosol) CH O-CO-R 2 CH O 2 R’-CO-OCH P Cardiolipin Phosphatidylglycerol Acetylcholine Glycerophosphocholine Lysolecithin Choline plasmalogen CDP-choline Choline-P Mevaldate CH (CH ) CH=CHCH(OH)CHCH OH 3 2 12 2 Dehydrosphinganin Sphinganin 4-Sphingenin Psychosine Acyl-CoA Acyl-CoA Cerebroside Galactose CH (CH ) CH=CHCH(OH)CHCH O- 3 2 12 2 NHCOR Isopentenyl-PP (C5) Dimethylallyl-PP (C5) Geranyl-geranyl-PP (C20) Farnesyl-PP (C15) Squalene (C30) Geranyl-PP (C10) Desmosterol Zymosterol Lanosterol CH C = CHCH O 3 2 PP 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 CO2 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 OCH2C 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 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 HOCH2COCH2OP 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 2n+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 2NH3 + 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 NH3 + CH (CH ) CH(OH)CHCH OH 3 2 14 2 NH3 + CH (CH ) COCHCH OH 3 2 14 2 NH3 + Galactose CH (CH ) CH=CHCH(OH)CHCH O- 3 2 12 2 NH3 + 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 POOCCH 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 2CH(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 OP~ ~ P O O PO O CH2 N N N N O OH OH NH2 HC CH N N N N 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 2 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 CH2 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 ) + 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 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 UQH2drives the translocation of protons from the matrix to the intermembrane space. Theretrolocationof 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 T R A N S L O C A T E D PROTONS 2.7.1.1 ATP 2.7.1.2 Metabolic Pathways Metabolic 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. Free Tel: 800-565-1400 Free Fax: 800-265-3858 Tel: 905-829-9500 Fax: 905-829-9292 China SIGMA-ALDRICH CHINA INC. Tel: 86-21-6386 2766 Fax: 86-21-6386 3966 Czech Republic SIGMA-ALDRICH s.r.o. Tel: 246 003 200 Fax: 246 003 291 Denmark SIGMA-ALDRICH DENMARK A/S Tel: 43 56 59 10 Fax: 43 56 59 05 Finland SIGMA-ALDRICH FINLAND Tel: 358-9-350-92 50 Fax: 358-9-350-92 555 France SIGMA-ALDRICH CHIMIE S.à.r.l. Tel appel gratuit: 0800 211 408 Fax appel gratuit: 0800 031 052 Germany SIGMA-ALDRICH CHEMIE GmbH Free Tel: 0800-51 55 000 Free Fax: 0800-649 00 00 Greece SIGMA-ALDRICH (O.M.) LTD Tel: 30 210 9948010 Fax: 30 210 9943831 Hungary SIGMA-ALDRICH Kft Tel: 06-1-235-9054 Fax: 06-1-269-6470 Ingyenes zöld telefon: 06-80-355-355 Ingyenes zöld fax: 06-80-344-344 India SIGMA-ALDRICH CHEMICALS PRIVATE LIMITED Telephone Bangalore: 91-80-5112-7272 Hyderabad: 91-40-5531 5548 / 2784 2378 Mumbai: 91-22-2579 7588 / 2570 2364 New Delhi: 91-11-2616 5477 / 2619 5360 Fax Bangalore: 91-80-5112-7473 Hyderabad: 91-40-5531 5466 Mumbai: 91-22-2579 7589 New Delhi: 91-11-2616 5611 Ireland SIGMA-ALDRICH IRELAND LTD. Free Tel: 1800 200 888 Free Fax: 1800 600 222 Israel SIGMA-ALDRICH ISRAEL LTD. Tel: 08-948-4100 Fax: 08-948-4200 Italy SIGMA-ALDRICH S.r.l. Telefono: 02 33417310 Fax: 02 38010737 Numero Verde: 800-827018 Japan SIGMA-ALDRICH JAPAN K.K. Tokyo Tel: 03 5821 3111 Tokyo Fax: 03 5821 3170 Korea SIGMA-ALDRICH KOREA Tel: 031-329-9000 Fax: 031-329-9090 Malaysia SIGMA-ALDRICH (M) SDN. BHD Tel: 603-56353321 Fax: 603-56354116 Mexico SIGMA-ALDRICH QUÍMICA, S.A. de C.V. Free Tel: 01-800-007-5300 Free Fax: 01-800-712-9920 The Netherlands SIGMA-ALDRICH CHEMIE BV Tel Gratis: 0800-0229088 Fax Gratis: 0800-0229089 Tel: 078-6205411 Fax: 078-6205421 New Zealand SIGMA-ALDRICH PTY., LIMITED Free Tel: 0800 936 666 Free Fax: 0800 937 777 Norway SIGMA-ALDRICH NORWAY AS Tel: 23 17 60 60 Fax: 23 17 60 50 Poland SIGMA-ALDRICH Sp. z o.o. Tel: (+61) 829 01 00 Fax: (+61) 829 01 20 Portugal SIGMA-ALDRICH QUÍMICA, S.A. Free Tel: 800 20 21 80 Free Fax: 800 20 21 78 Russia SIGMA-ALDRICH RUSSIA TechCare Systems, Inc. (SAF-LAB) Tel: 095-975-1917/3321 Fax: 095-975-4792 Singapore SIGMA-ALDRICH PTE. LTD. Tel: 65-6271 1089 Fax: 65-6271 1571 South Africa SIGMA-ALDRICH SOUTH AFRICA (PTY) LTD. Tel: 27 11 979 1188 Fax: 27 11 979 1119 Spain SIGMA-ALDRICH QUÍMICA S.A. Free Tel: 900101376 Free Fax: 900102028 Sweden SIGMA-ALDRICH SWEDEN AB Tel: 020-350510 Fax: 020-352522 Outside Sweden Tel: +46 8 7424200 Outside Sweden Fax: +46 8 7424243 Switzerland FLUKA CHEMIE GmbH Swiss Free Call: 0800 80 00 80 Tel: +41 81 755 2828 Fax: +41 81 755 2815 United Kingdom SIGMA-ALDRICH COMPANY LTD. Free Tel: 0800 717181 Free Fax: 0800 378785 Tel: 01747 833000 Fax: 01747 833313 United States SIGMA-ALDRICH P.O. Box 14508 St. Louis, Missouri 63178 Toll-free: 800-325-3010 Call Collect: 314-771-5750 Toll-Free Fax: 800-325-5052 Tel: 314-771-5765 Fax: 314-771-5757 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 Product No. M 3907 XXX

Upload: at-eazz

Post on 07-Oct-2014

155 views

Category:

Documents


11 download

Report

TRANSCRIPT

Page 1: Sigma Metabolic Pathways

sigma-aldrich.com/pathways

2H+

H+

OXALOACETATE

PYRUVATE

SUCCINYL-CoA

GLUTARATE

CITRATE

MALATE

2-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+

F0

F1

F1

!2

1 "!

"

#

0 c-sub-units

AD

P+ Pi

3.6.1.34

H

+-transporting ATP synthase

"

$F6

oscp

ATP

ADP +Pi

FUMARATE

UQH2

UQ

UQH2

NADH+H+CH2COO-

C(OH)COO-

CH2COO-

CH(OH)COO--

2COO-

-OOCCOCH2CH2COO-

-OOCCH2CH2CO.SCoA

-OOCCOCH2COO-

CH3CH(OH)CH2CO.SCoA

-OOCCH=CHCOO-

Glyoxylate Cycle

-OOCCHO

GTP

GDPATP

+

HEME Protoporphyrinogen Coproporphyrinogen Uroporphyrinogen Porphobilinogen

5-Amino-levulinate

COO-

CH2

CH2H2NCH2C=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

5.1.99.1

5.4.99.2

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

#

%$

!

33 !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

2!

88

H+c

32

%

a

32

"1

"

%

"

!2

1

3

"

"!

3

"

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+

#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

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 2

3-OH-ButyrateAcetone

Acetoacetate

KETONE BODIES

HYALURONIC ACID DERMATAN BLOOD GROUPSUBSTANCES

PEPTIDO-GLYCAN

N-Ac-Neuraminate(Sialate)

UDP-Iduronate

UDP-N-Ac-Galactosamine UDP-

Galacturonate

GDP-Fucose

TDP-Rhamnose

ADP-Glucose

UDP-Glucose

TDP-4-Oxo-6-deoxyglucose

MANNOSE

CHITIN CHONDROITIN PECTIN

ALGINATES

INULIN CELLULOSE

O-ANTIGENS STARCH GLYCOGEN

LACTOSE

GALACTOSE

O

OH

HO

OH

OH

CH3 O

OPPTO

OH

OH

O

OHACNH

HO OH

O

OHHO OPPU

NHAC

OH

OH OH

OH

HO

OH

NHCOCH

OH HO

O

OPPG

CH OH2

HO

P

UDP-N-Ac-Glucosamine

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

GDP-Mannose

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

Sorbitol

Fructose-1-P

Erythrose-4-P

3-Dehydrogulonate

L-Xylose

L-Lyxose

D-Xylulose

D-Ribose

RibitolL-Arabitol L-Xylulose

L-Ribulose L-Ribulose-5-P

L-Xylulose-5-P

L-Arabinose Xylitol D-Xylose

D-Arabinose D-Ribulose

ASCORBATE

2, 3-Dioxogulonate

N-Ac-Glucosamine-1-P

Inositol-PInositolGlucuronateGulonate

Gulonolactone 2-Oxogulonolactone

Fructose

6-P-Gluconate

D-Ribulose-5-P

D-Xylulose-5-P

Mannose-1-P

GDP-Glucose

TDP-Glucose

UDP-Galactose

Galactose-P

Glucose-1-P

Glucose-6-P

Fructose-6-P

Fructose-1:6-bis-P

OH

H H HO

HOCH2 C C C C CO

OH OHH OH

H HO

HOCH2 C C C CO CO

OHH

H

OH H

C C

OH

CO

P-Ribosylamine

Glycerate2, 3-Diphospho-glycerate

3-P-Glyceraldehyde

1:3-bis-P-Glycerate

3-P-Glycerate

2-P-Glycerate

P-enolpyruvate

Inositol

CH OH2

CH OH2

HOCH

CH OH2

CH O2

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

NH

Indole-acetaldehyde

NH

CH CHO2

Indolepyruvate

NH

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

2-Aminomuconate-6-semialdehyde

CH CH NH2 2 2

NH

1.2.3.7

4.1.1.43

3.5.1.9 3.7.1.3

4.2.1.20

1.13.11.6 4.1.1.45

2.4.2.18

4.6.1.4

4.1.1.48

1.14.13.9

4.6.1.3 Dehydro-quinate

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

ChorismatePEP

2.7.1.71

1.4.1.19

Homogentisate Phenylpyruvate

Cinnamate

Coumarate

Prephenate

2-Aminomuconate

Fumarate Aspartate

GLYCINE

Sarcosine

Hydroxy-pyruvate

P-Hydroxy-pyruvate

SERINE

Imidazoleglycerol-P

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

Formiminoglutamate

Imidazolonepropionate

Urocanate

Cystathionine Homocysteine

Phosphoadenylyl-sulphate

(PAPS)

CH (NH )COOH2 3+

Histidinol-PHistidinolHistidinal3.1.3.15 2.6.1.91.1.1.23

3.6.1.31

5.3.1.162.4.2.17

Asparagine

ALANINE

3-Sulphinylpyruvate

Oxobutyrate

2-Aceto-2-hydroxy-butyrate

O-Phospho-homoserine

HO SCH CH NH2 2 2 2

HypotaurineHO SCH CH NH3 2 2 2

Taurine

Glutamate

#-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

#-Linolenate Arachidonate Leukotriene B4

COSCoA

CO-S-ACP

Thromboxane B2

HOOCCH CO-S-ACP2Malonyl-ACP

HOOCCH CO-SCoA2

Malonyl-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

AcetylcholineGlycerophosphocholine

Lysolecithin

Cholineplasmalogen

CDP-choline Choline-P

Mevaldate

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

Dehydrosphinganin Sphinganin 4-Sphingenin Psychosine

Acyl-CoAAcyl-CoA

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

NHCOR

Isopentenyl-PP(C5)

Dimethylallyl-PP(C5)

Geranyl-geranyl-PP(C20)

Farnesyl-PP(C15)

Squalene(C30)

Geranyl-PP(C10)

Desmosterol Zymosterol Lanosterol

CH C = CHCH O3 2 PP

CH3

Ceramide

Gangliosides

NHCOR

CH O2 PP

OPPCH2

CHOLESTEROL

CH C(OH)CH CH OH3 2 2

CH COO2

CH C(OH)CH CHO3 2

CH COO2

NADP+Dehydroascorbate

OH

H O

HOCH2 C C C C CO

OHH OH

OH

H O

HOCH2 C C CO CO CO

H

NAD+Pi

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)

Opsin

CHO

CH OH2

CHO

CH OH2

CH3CH O3

CH O3 n

O

O

O

O

Phytol (C20)

"-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 P

NHCOCH NH2 2

OHFormyl

glycinamide-R P

Urea

Formylglycinamidine-R P

Allantoate Allantoin URATE

ADP

Xanthine Hypoxanthine

Inosine

Adenine

Adenylo-succinate

5-Aminoimidazole-R P

5-Amino-4-imidazolecarboxylate-R P

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

5-Aminoimidazolecarboxamide-R P

Formylamido-imidazole-

carboxamide-R P

H NCONH2 2

HNH C2 CHO

NHRP

NH

C

CCO

CCO

OCNH

NH

HN

HN

H

CCO

CCH

OCNH

N

N

HN

Carbamoylß-alanine

Dihydro-uracil Uracil

d-ADP

d-ATP

GTP GDP

XANTHOSINE-P(XMP)

TTP

TDP

ß-Ureidoisobutyrate

Dihydrothymine

Thymine d-UMP d-CMP d-CDP

CDP

Carbamoylaspartate

Dihydroorotate

Orotate Orotidine-P Uridine-P(UMP)

UDP

3-Amino-isobutyrate

CHCNH2

CHOCNH

NCHCO

CHOCN H

HN

CH-CH3CO

OCNH

HNCH2

CH2CH2

CO

OCNH

HN

CO

CHOCNH

HN C CH3

Methylmalonylsemialdehyde

OHCCHCOOCH3

CH2CO

CH-COOOCNH

HN CHCO

C-COOOCNH

HN

H NCONHCH CH COO2 2 2

CC

CCH

RPHC

NH

NH OOC-CH-CH COO2

N

N

N

CHO

NH RP

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

1.3.1.101.3.1.9

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

3.1.4.3

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

6.3.5.16.3.1.5

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

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

"-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

2.7.7.62.7.7.6

2.7.7.6

2.7.7.6

2.7.4.62.7.4.32.7.4.4

2.7.4.6

2.4.2.15

1.1.1.205

6.3.4.16.3.5.2

2.7.4.4

3.5.4.3

3.2.2.2

2.4.2.1

3.1.3.5

3.1.4.6

6.3.4.2

1.17.4.1

1.17.4.1

3.5.4.12

2.7.4.8

2.7.4.9

2.7.4.6

2.4.2.4

1.3.1.2

3.5.2.23.5.1.6

3.5.1.6 3.5.2.2 3.5.4.1

Diphospho-mevalonate

Mevalonate

3-Oxopentanoyl-CoA

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

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

Acetoacetyl-CoA3-OH-Butanoyl-CoACrotonoyl-CoA

Pentanoyl-CoA 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

1.2.1.11

4.2.1.52 1.3.1.26 Piperideine-2, 6-dicarboxylate

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

pimelate

2.6.1.17N-Succinyl-2, 6diaminopimelate

Diamino-pimelate

3.5.1.18

3-Methyl-glutaconyl-CoA

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

3-Methyl-crotonyl-CoA

Isovaleryl-CoA

OxopantoateHCHO

OOCCH C = CHCOSCoA2

CH3

CH COCHCOSCoA3

CH3

CH CH=CHCOSCoA3

CH3CH CH(OH)CHCOSCoA3

CH3

C(OH)CH(OH)COOCH CH3 2

CH3

CH = CCOSCoA2

CH3HOCH CHCOS-CoA-2

CH3

CH CHCO-SCoA3

CH3

C (OH)CH(OH)COOCH3

CH3

CH CH CHCOSCoA3 2

CH3

CH C = CHCOSCoA3

CH3

ATP

4-Aminobutyrate(GABA)

1.3.99.7

1.5.1.2

1.14.11.2

2.6.1.39 1.2.1.31

1.14.11.8

2.5.1.16

2.5.1.22

4.1.3.16

2.6.1.23

1.5.99.8

1.5.1.2

6.4.1.4 1.3.99.10

4.2.1.33

2.6.1.6

1.1.1.85Oxoleucine

COOH

(CH ) CHCHCH(OH)COO3 2

S-Adenosylmethylthiopropylamine

(Decarboxylated SAM)

PROLINE

Coenzyme A

CH C= CHCH3 2

CH3

OCH

CH

3

3HO

CH3CH3

CH3

CH C-CH H O3 2 2C PP

CH2

CH C= CHCH O2 2 PP

CH3

3-P-Glycerol

Phosphatidylethanolamine

CEPHALIN

3.1.4.12

2.7.8.3

Progesterone

1.5.1.12

2.7.3.2

4.2.1.173.1.2.4

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

1.4.3.4

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

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

4.2.1.52

1.2.1.18

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 C

CONH2

CCH

HCN

RP

N

N

NHP

+OOCCH N(CH )2 3 3

Betaine

Betainealdehyde

2.4.1.16

5.1.3.6

2.4.1.33

2.7.7.13

5.4.2.8

5.3.1.8

O

OH

CH OH2

HO

O PHO

2.7.1.28

2.7.1.31

6.3.4.13

5.3.1.1

2.2.1.1

4.1.1.9

3.1.2.11

ß-OH-ß-Methyl-glutaryl-CoA

6.3.4.5

5.3.1.6

2.5.1.21

2.1.1.2

3.5.2.10

6.3.2.136.3.2.7-10

2.7.7.27

2.7.7.9

3.5.4.10

CCO

CCH

OCN RP

N

NH

HN

CCO

CCH

N

N

N

HN

RPH N2 C

2.7.4.6

1.17.4.1

2.7.4.6

2.6.1.13

Carbamoyl-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

OH

OPPU

CH OH2

O

O

HO

OH

OH

HO

P

CH OH2

CH OH2O

OHO

OH

OH

O

OHOH

OH

CH OH2

O

OHHO

OH

OH

CH2CH OP2

OH

H H HOH

C C C C

OH OHH

COO-HOCH2

H

OH OHOH

C C C CHO

HH

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 OH

C 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 2

Pentenoyl-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-PO

O-

HOCH CH2 2NH3+POCH CH2 2NH3

+CPP- OCH CH2 2NH3

+

O

-

CH O-CO-R2

CH O P2 OCH CH2 2NH3+

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

HOCH CH N(CH )2 2 3 3

+

CH CH 2 COO(NH )3+

OHOH

CH CH 2 COO-(NH )3+

CO

NH2

CH CH(NH )COO2 3+

NHOC

CO

NHOC

NH

CH

H N2

HCCH

N

N

C

RPH N2

CHC

CHOCN

N

DP

NH2

RPPP

CHC

CHOCN

N

NH2

CC

CCH

RP(P)HC

N

N

N

N

NH2

H NCOO2 P

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

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

CH -SCH CH CHNH3 2 2 2

Adenosyl

+

+CH3

CH3

CHCH(NH )COO3

++C

NHNC

HC

H

CH CH(NH )CH OH2 3 2

+C

NHNC

HC

H

CH CH(NH )CH OP2 3 2C

NHNCH

HC CH COCH OP2 2

+HSCH CH CH(NH )COO2 2 3

+

+SCH CH CH(NH )COO2 2 3

CH CH(NH )COO2 3

RP

CO

C-COOOCN

HN CH

2.4.1.23

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

O

CH CH3

COO-

NHAC

HO OPPU

CH OH2

4.1.3.20

O

OH

CH3

HO HO OPPG

2.7.7.24

2.4.1.22

2.7.7.12

5.1.3.2

5.3.1.4

Sedoheptulose-PP

3.1.1.28

4.2.1.24

N

CH2

CH2

N

N

N

CH3

CH3

CH

CH

COO

CHCH

CH2

H C3

H C3H C3

HC

C

C

H

H

Fe

CH2

CH2

COO- -

CH3

CH3

CH2

CH2

CH2

H C3

H C3N

H

NH

NH

NH

CH

CH

H C2

C

CH2

H2

-

CH2

CH2

COO

CH2

CH2

COO -

H C2

H C2

CH 2

CH 2

OOC

COO

H N2

NH

-

-

CH2

H C2

H C2

H C2

H2

H2

CH2

CH2 CH2

CH2

CH2

CH2

NH

NH

NH

NH

COO

COO

COOCOO

C

C

--

CH2

CH2

COO

CH2

CH2

COO- -

-

-

OOC-

OOC-

CH3

CH3

H C3

H C3

H C2

H2

H2

NH

NH

NH

NH

CH2

CH2

CH2

CH2

CH2

C

C

COO-

CH2

CH2

COO

CH2

CH2

COO- -

COO-

COO-

CH C(OH)CH CH O3 2 2 PP

CH COO2

OHCCOO

HOCH COO2

NH2

H NCNHCH COO2 2

+ NH2

H NCN(CH )CH COO2 3 2

+ NH2

HNCN(CH )CH COO3 2P-

+ HN CNH CO

N CH2

CH3

OOCCHCH COO2

H NCNHCH CH CH CH2 2 2 2

N(NH )3+

COO

CHCOOHC

CH2HOCH

N

OOCCH(OH)CH CH(NH )COO2 3

+

CHCOO

CH2HOCH

H C2NH

NH

CHCOO

CH2CH2

CH2

OOCCH(OH)CH COCOO2

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 2

NH3+

NH3+

(CH ) CHC(OH)CH3 2 2

COOH

COO (CH ) CHCH COCOO3 2 2

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

HOCH CHCOO2

CH3

CHCOCOO

CH3

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

CH3

CH+

CH(NH )COO3

CH COC(OH)CH CH3 2 3

COO CHCOCOO

CH CH3 2

CH3

NHCHCH SH2

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

+ CH SH2 OOCCH(NH )CH CH CONHCHCOO3 2 2

+AdenosylSCH CH CH(NH )COO2 2 3

+SCH CH CH(NH )COO2 2 3

+HO SCH CH(NH )COO3 2 3

+

+S-CH CH(NH )COO2 3

S-CH CH(NH )COO2 3+

HSCH CH(NH )COO2 3

1.1.1.23

H

C

NHNC

HC CH CHCOO2

NHCOCH CH NH2 2 2+

H

C

NHNC

HC CH CH(NH )COO2 3

CHCH CH COO2 2

NHNCH

OC C CH CHCOO

NHNCH

CH

CH COO3

NH

OOC

CH-COOOCNH2 CH2

H NCH CH COO2 2 2

H NCH2 2

CH3CHCOO H NCONHCH CHCOO2 2

CH3

CCO

CH

RPHC N

N

N

HN

C

CCO

CHHCO

N

N

N RP

CCH

N

NH N2

HC

CCO

CH

N

NC

CCH

N

N

RP

H N2

H N2C

O

O

O P~ ~P O

O

O O

P O

O

CH2

N

N

N

N

O

OHOH

NH2

HCCHN

N

N

N O

O

P O O

O

CH2

OH

NH2

HCCH

COOCO

NHOC

NH

CH

H N2NH2

OOC-CH-CH COO2

HNCO CCH

N

N

C

RPRPH N2

OOCC

CH

NRP

N

CH N2

CH=CHCOO

OH

CH=CHCOO

CH COCOO2

CH2

P

COO

OHO

O

O

COO

O

CH COO2OCH COO2-OOC

OCH2 CH2

OHHC

P

HOCH HCOH

OCCOO

COOHO

OHOHO

NH2COOOCH

NH

CH COCOO2NH

CHO

CO

NH2OH

CH CH(NH )COO2 3+

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 2

Dimethylglycine

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 CH 2 COO(NH )3+Epinephrine

(Adrenaline)Norepinephrine

(Noradrenaline)

Normetepinephrine(Normetadrenaline)

HOCH CH N(CH )2 2 3 3+

Adenosyl+

+SCH CH CH(NH )COO2 2 3

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 POCMP2

O

CH CH N(CH )2 2 3+

OHOCH

CH OPO2

CH OH2

O-

CH OPO2

O

CH OCH=CHR2

CH CH N(CH )2 2 3 3+

O-CH OPO2

OR'-CO-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

4.2.1.46

2.7.1.7

2.4.1.29

2.4.1.21

2.4.1.13

2.4.1.1etc.

5.4.2.2

2.7.1.6

2.7.7.10

3.1.1.18

4.1.1.34

2.7.1.47

2.7.1.16

3.1.3.9

ADP

P-Gluconolactone

1.1.1.44

O

OOHHO

OH

CH O2 P

PHENYLALANINETYROSINE

TRYPTOPHAN

INOSINE-P(IMP)

THYMIDINE-P

HISTIDINE

URIDINE-triphosphate

(UTP)

CYSTINE CYSTEINE

ISOLEUCINE

LEUCINE

LYSINE

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

PO

O

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

NHAcyl

CH CH N(CH )2 2 3 3+

O-

3.5.1.23

1.13.11.21

2.5.1.32

1.1.1.105

2.4.2.19

1.2.1.32

METHIONINE

4.1.3.27

4.2.1.51

1.14.17.1

1.14.18.1

1.14.13.11

Glycinamide-ribosyl-P

4.2.1.22

3-Oxohexanoyl-CoA

THREONINE

1.2.1.25

1.2.1.25

1.2.1.25

1.5.1.7 - 10

GLUTAMATE

2.3.1.38

ATP

NADH

SUCROSE

ADENOSINE-P(AMP)

TriacylglycerolFAT

RNA

CH3

CH2

OC-COOOH

COO

CH CH 2 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’2

OR'-CO-OCH

O-

CH O-CO-R2

CH O-PO2O-

2.7.8.11

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

+

2.3.1.20 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

LOC

ATED PROTONS

2.7.1.1

ATP2.7.1.2

Metabolic PathwaysMetabolic Pathways

ArgentinaSIGMA-ALDRICH DE ARGENTINA, S.A.Tel: 54 11 4556 1472Fax: 54 11 4552 1698

AustraliaSIGMA-ALDRICH PTY., LIMITEDFree Tel: 1800 800 097 Free Fax: 1800 800 096Tel: 612 9841 0555Fax: 612 9841 0500

AustriaSIGMA-ALDRICH HANDELS GmbHTel: 43 1 605 81 10Fax: 43 1 605 81 20

BelgiumSIGMA-ALDRICH NV/SA.Free Tel: 0800-14747Free Fax: 0800-14745Tel: 03 899 13 01Fax: 03 899 13 11

BrazilSIGMA-ALDRICH BRASIL LTDA.Tel: 55 11 3732-3100Fax: 55 11 3733-5151

CanadaSIGMA-ALDRICH CANADA LTD.Free Tel: 800-565-1400Free Fax: 800-265-3858Tel: 905-829-9500Fax: 905-829-9292

ChinaSIGMA-ALDRICH CHINA INC.Tel: 86-21-6386 2766Fax: 86-21-6386 3966

Czech RepublicSIGMA-ALDRICH s.r.o.Tel: 246 003 200Fax: 246 003 291

DenmarkSIGMA-ALDRICHDENMARK A/STel: 43 56 59 10Fax: 43 56 59 05

FinlandSIGMA-ALDRICH FINLANDTel: 358-9-350-92 50Fax: 358-9-350-92 555

FranceSIGMA-ALDRICH CHIMIE S.à.r.l.Tel appel gratuit: 0800 211 408Fax appel gratuit: 0800 031 052

GermanySIGMA-ALDRICH CHEMIE GmbHFree Tel: 0800-51 55 000Free Fax: 0800-649 00 00

GreeceSIGMA-ALDRICH (O.M.) LTDTel: 30 210 9948010Fax: 30 210 9943831

HungarySIGMA-ALDRICH KftTel: 06-1-235-9054Fax: 06-1-269-6470Ingyenes zöld telefon: 06-80-355-355Ingyenes zöld fax: 06-80-344-344

IndiaSIGMA-ALDRICH CHEMICALS PRIVATE LIMITEDTelephoneBangalore: 91-80-5112-7272Hyderabad:91-40-5531 5548 / 2784 2378Mumbai:91-22-2579 7588 / 2570 2364New Delhi:91-11-2616 5477 / 2619 5360FaxBangalore: 91-80-5112-7473Hyderabad: 91-40-5531 5466Mumbai: 91-22-2579 7589New Delhi: 91-11-2616 5611

IrelandSIGMA-ALDRICH IRELAND LTD.Free Tel: 1800 200 888Free Fax: 1800 600 222

IsraelSIGMA-ALDRICH ISRAEL LTD.Tel: 08-948-4100Fax: 08-948-4200

ItalySIGMA-ALDRICH S.r.l.Telefono: 02 33417310Fax: 02 38010737Numero Verde: 800-827018

JapanSIGMA-ALDRICH JAPAN K.K.Tokyo Tel: 03 5821 3111Tokyo Fax: 03 5821 3170

KoreaSIGMA-ALDRICH KOREATel: 031-329-9000Fax: 031-329-9090

MalaysiaSIGMA-ALDRICH (M) SDN. BHDTel: 603-56353321Fax: 603-56354116

MexicoSIGMA-ALDRICH QUÍMICA,S.A. de C.V.Free Tel: 01-800-007-5300Free Fax: 01-800-712-9920

The NetherlandsSIGMA-ALDRICH CHEMIE BVTel Gratis: 0800-0229088Fax Gratis: 0800-0229089Tel: 078-6205411Fax: 078-6205421

New ZealandSIGMA-ALDRICH PTY., LIMITEDFree Tel: 0800 936 666Free Fax: 0800 937 777

NorwaySIGMA-ALDRICH NORWAY ASTel: 23 17 60 60Fax: 23 17 60 50

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

PortugalSIGMA-ALDRICH QUÍMICA, S.A.Free Tel: 800 20 21 80Free Fax: 800 20 21 78

RussiaSIGMA-ALDRICH RUSSIATechCare Systems, Inc.(SAF-LAB)Tel: 095-975-1917/3321Fax: 095-975-4792

SingaporeSIGMA-ALDRICH PTE. LTD.Tel: 65-6271 1089Fax: 65-6271 1571

South AfricaSIGMA-ALDRICHSOUTH AFRICA (PTY) LTD.Tel: 27 11 979 1188Fax: 27 11 979 1119

SpainSIGMA-ALDRICH QUÍMICA S.A.Free Tel: 900101376Free Fax: 900102028

SwedenSIGMA-ALDRICH SWEDEN ABTel: 020-350510Fax: 020-352522Outside Sweden Tel: +46 8 7424200Outside Sweden Fax: +46 8 7424243

SwitzerlandFLUKA CHEMIE GmbHSwiss Free Call: 0800 80 00 80Tel: +41 81 755 2828Fax: +41 81 755 2815

United KingdomSIGMA-ALDRICH COMPANY LTD.Free Tel: 0800 717181Free Fax: 0800 378785Tel: 01747 833000Fax: 01747 833313

United StatesSIGMA-ALDRICHP.O. Box 14508St. Louis, Missouri 63178Toll-free: 800-325-3010Call Collect: 314-771-5750Toll-Free Fax: 800-325-5052Tel: 314-771-5765Fax: 314-771-5757Internet: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-AldrichProduct No. M 3907

XXX

Organizing and Computing Metabolic Pathways

necrophorum: biofilms, glycans and metabolic pathways

Variations in metabolic pathways create challenges for ...biology.polytechnique.fr/biocomputing/papers/Comp6_Crecy_Folate.pdf · Mini Review Variations in metabolic pathways create

Topic 2: Molecular Biology 2.1 – 2.4 The background is just a small part of the IUBMB-Sigma-Nicholson Metabolic Pathways Chart aims to show all the metabolic

38 Metabolic Pathways 2

Topic guide 1.7: Metabolic pathways - contentextra.com

Pathways & Molecules M.A. Ott (CMBI). Contents Pathways and Molecules M.A. Ott Enzymes and Metabolites Metabolic Pathways: Cholesterol Biosynthesis Metabolic

19. ENZYMES AND METABOLIC PATHWAYS

CATABOLIC PATHWAYS AND METABOLIC CONTROLS IN …

Metabolic Pathways 2003 - Georgia Institute of Technologyturk/bio_sim/articles/metabolic_pathways_2006.pdf · Title: Metabolic Pathways 2003 Author: Sigma-Aldrich Subject: Optimized

METABOLIC PATHWAYS AFFECTING MITOCHONDRIAL …

Metabolic Pathways Chart

Metabolic Pathways Exploring pathways and compoundsNavigate to the search page for Identify Metabolic Pathways based on Pathway Name/ID. − Metabolic pathway and compound searches

Revision Metabolic Pathways

Visual Understanding of Metabolic Pathways Across

Compartmentalisation of metabolic pathways

Cellular Pathways Metabolic pathways occur in small steps, each catalyzed by a specific enzyme. Metabolic pathways are often compartmentalized and are

Metabolic pathways of_diseased_potato

Three Metabolic Pathways. Pathways of Cell Respiration 2 234

Typical network of metabolic pathways

Reconstruction of Metabolic Pathways by Combining ...calla.rnet.missouri.edu/cheng_courses/metabolic_pathway_v12.pdf · Reconstruction of Metabolic Pathways by Combining Probabilistic

Syntactic Model of Metabolic Pathways

Phytochemistry - Evolution of Metabolic Pathways

CORRELATION BETWEEN METABOLIC PATHWAYS

Metabolic Pathways and Energy Production - … 18 Metabolic Pathways ... Chapter 18 Metabolic Pathways and Energy Production . 18.4 . ... Reaction 4: Oxidative

Library of Apicomplexan Metabolic Pathways: a manually ... · Library of Apicomplexan Metabolic Pathways: a manually curated database for metabolic pathways of apicomplexan parasites

Metabolic Pathways in Methanococcus jannaschii and

Homomorphism Mapping in Metabolic Pathways

Types of Metabolic Pathways

Metabolism Energy of Life. Metabolic Pathways Anabolic PathwaysCatabolic Pathways

Metabolic Pathways

Mapping Dysregulated Metabolic Pathways in Cancer …digitalassets.lib.berkeley.edu/etd/ucb/text/Benjamin_berkeley_0028... · Mapping Dysregulated Metabolic Pathways in Cancer Using

Altered metabolic energy pathways and cancer

METABOLIC PATHWAYS - Jiwaji University · 2020. 4. 7. · Metabolic pathways are mostly irreversible 2. Every metabolic pathway has a committed first step. 3. All metabolic pathways

Bioenergetics and metabolic pathways · Bioenergetics and metabolic pathways ... • Introduction to Bioenergetics • Metabolism • Metabolic Pathways ... Principles of Anatomy