Metabolic Modeling Tutorial
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: carbon monoxide

Synonyms: CO, carbon monooxide

Chemical Formula: CO

Molecular Weight: 29.018 Daltons

Monoisotopic Molecular Weight: 29.0027396542 Daltons

SMILES: [C-]#[O+]

InChI: InChI=1S/CO/c1-2

InChIKey: InChIKey=UGFAIRIUMAVXCW-UHFFFAOYSA-N

Unification Links: CAS:630-08-0 , ChEBI:17245 , ChemSpider:275 , HMDB:HMDB01361 , KEGG:C00237 , MetaboLights:MTBLC17245 , PubChem:281

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -32.8 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

carbon tetrachloride degradation II , hydrogen production VI :
carbon monoxide + an oxidized electron acceptor + H2O → CO2 + a reduced electron acceptor

Reactions known to produce the compound:

3-methylthiopropanoate biosynthesis :
1,2-dihydroxy-5-(methylthio)pent-1-en-3-one + oxygen → 3-(methylthio)propanoate + formate + carbon monoxide + H+

4-amino-2-methyl-5-diphosphomethylpyrimidine biosynthesis :
5-amino-1-(5-phospho-β-D-ribosyl)imidazole + S-adenosyl-L-methionine → 4-amino-2-methyl-5-phosphomethylpyrimidine + 5'-deoxyadenosine + L-methionine + formate + carbon monoxide + 3 H+

alkane biosynthesis II :
a long-chain aldehyde → an alkane + carbon monoxide

carbon tetrachloride degradation II :
dichlorocarbene + H2O → carbon monoxide + 2 chloride + 2 H+

cuticular wax biosynthesis :
a very-long-chain aldehyde → an alkane + carbon monoxide

heme degradation , phycocyanobilin biosynthesis , phycoerythrobilin biosynthesis , phytochromobilin biosynthesis :
ferroheme b + 3 a reduced electron acceptor + 3 oxygen + 2 H+ → biliverdin-IX-α + Fe2+ + carbon monoxide + 3 an oxidized electron acceptor + 3 H2O

rutin degradation :
quercetin + oxygen → 2-protocatechuoylphloroglucinolcarboxylate + carbon monoxide

Not in pathways:
3-hydroxy-1H-quinolin-4-one + oxygen → carbon monoxide + N-formylanthranilate
3-hydroxy-2-methyl-1H-quinolin-4-one + oxygen → carbon monoxide + N-acetylanthranilate
ferroheme b + 4 a reduced electron acceptor + 4 oxygen + 2 H+ → 15-oxo-β-bilirubin + Fe2+ + carbon monoxide + 4 an oxidized electron acceptor + 4 H2O
ferroheme b + 4 a reduced electron acceptor + 4 oxygen + 2 H+ → 5-oxo-δ-bilirubin + Fe2+ + carbon monoxide + 4 an oxidized electron acceptor + 4 H2O

Reactions known to both consume and produce the compound:

methanogenesis from acetate :
acetyl-CoA + a [Co(I) corrinoid Fe-S protein] ↔ carbon monoxide + a [methyl-Co(III) corrinoid Fe-S protein] + coenzyme A
carbon monoxide + an oxidized ferredoxin + H2O ↔ CO2 + a reduced ferredoxin + H+

reductive acetyl coenzyme A pathway :
acetyl-CoA + a [Co(I) corrinoid Fe-S protein] ↔ carbon monoxide + a [methyl-Co(III) corrinoid Fe-S protein] + coenzyme A
carbon monoxide + an oxidized ferredoxin + H2O ↔ CO2 + a reduced ferredoxin + H+

In Reactions of unknown directionality:

Not in pathways:
carbon monoxide + H2O = CO2 + H2
carbon monoxide + 2 an oxidized cytochrome b561 + H2O = CO2 + 2 a reduced cytochrome b561 + 2 H+

In Transport reactions:
carbon monoxide[periplasmic space]carbon monoxide[cytosol]

Enzymes inhibited by carbon monoxide, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: acetylene hydratase [Meckenstock99]

Inhibitor (Noncompetitive) of: nitrogenase [Davis80, Zumft75, Allen94, Comment 1]

Inhibitor (Mechanism unknown) of: hydrogenase [Sawers86] , (R)-limonene 6-monooxygenase [Boumeester99] , quercetin 6-hydroxylase [Schlangen09] , quercetin 6-hydroxylase [Halbwirth04] , quercetin 6-hydroxylase [Halbwirth04] , autumnaline cytochrome P-450 oxidase [Nasreen96] , O-methylandrocymbine cytochrome P450 oxidase [Rueffer98] , β-phenylalanoyl baccatin III-2'-hydroxylase [Long05] , farnesyl methyl ester epoxidase [Hammock75] , benzoic acid 2-hydroxylase [Leon95] , calcitriol 24-hydroxylase [Ohyama91] , 25-hydroxyvitamin D3 1α-hydroxylase [Paulson85] , 5-β-cholestane-3α,7α,12α-triol 27-hydroxylase [Okuda88] , cholesterol 7α-hydroxylase [Ogishima87] , tryptophan dioxygenase [Brady75] , benzophenone-3'-hydroxylase [Schmidt97] , tryptophan dioxygenase [Matsumura84] , xanthone synthase [Peters98] , xanthone-6-hydroxylase [Schmidt00] , xanthone-6-hydroxylase [Schmidt00] , xanthone synthase [Peters98] , nitrogenase , salutaridine synthase [Gerardy93] , deoxypodophyllotoxin 6-hydroxylase [Molog01] , Piperitol synthase [Jiao98] , Sesamin synthase [Jiao98] , marmesin synthase [Hamerski88] , psoralen synthase [Hamerski88] , psoralen 5-monooxygenase [Hamerski88a]

Inhibitor (Other types) of: abieta-7,13-diene hydroxylase [Funk94] , C-22 sterol desaturase [Kelly95]


References

Allen94: Allen RM, Chatterjee R, Madden MS, Ludden PW, Shah VK (1994). "Biosynthesis of the iron-molybdenum cofactor of nitrogenase." Crit Rev Biotechnol 1994;14(3);225-49. PMID: 7954845

Boumeester99: Boumeester HJ, Konings MCJM, Gershenzon J, Karp F, Croteau R (1999). "Cytochrome P-450 dependent (+)-limonene-6-hydroxylation in fruits of caraway (Carum carvi)." Phytochemistry 50:243-248.

Brady75: Brady FO (1975). "Tryptophan 2,3-dioxygenase: a review of the roles of the heme and copper cofactors in catalysis." Bioinorg Chem 5(2);167-82. PMID: 178384

Davis80: Davis LC, Wang YL (1980). "In vivo and in vitro kinetics of nitrogenase." J Bacteriol 1980;141(3);1230-8. PMID: 6988410

Funk94: Funk C, Croteau R (1994). "Diterpenoid resin acid biosynthesis in conifers: characterization of two cytochrome P450-dependent monooxygenases and an aldehyde dehydrogenase involved in abietic acid biosynthesis." Arch Biochem Biophys 308(1);258-66. PMID: 8311462

Gerardy93: Gerardy, Roswitha, Zenk, Meinhart (1993). "Formation of salutaridine from (R)reticuline by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum." Phytochemistry, 32(1): 79-86.

Halbwirth04: Halbwirth H, Forkmann G, Stich K (2004). "The A-ring specific hydroxylation of flavonols in position 6 in Tagetes sp. is catalyzed by a cytochrome P450 dependent monooxygenase." Plant Science 167: 129-135.

Hamerski88: Hamerski D, Matern U (1988). "Elicitor-induced biosynthesis of psoralens in Ammi majus L. suspension cultures. Microsomal conversion of demethylsuberosin into (+)marmesin and psoralen." Eur J Biochem 171(1-2);369-75. PMID: 2828055

Hamerski88a: Hamerski D, Matern U (1988). "Biosynthesis of psoralens. Psoralen 5-monooxygenase activity from elicitor-treated Ammi majus cells." FEBS Lett 239(2);263-5. PMID: 3181429

Hammock75: Hammock BD (1975). "NADPH dependent epoxidation of methyl farnesoate to juvenile hormone in the cockroach Blaberus giganteus L." Life Sci 17(3);323-8. PMID: 1160503

Jiao98: Jiao Y, Davin LB, Lewis NG (1998). "Furanofuran lignan metabolism as a function of seed maturation in Sesamum indicum: Methylenedioxy bridge formation." Phytochemistry, 49(2), 387-394.

Kelly95: Kelly SL, Lamb DC, Corran AJ, Baldwin BC, Parks LW, Kelly DE (1995). "Purification and reconstitution of activity of Saccharomyces cerevisiae P450 61, a sterol delta 22-desaturase." FEBS Lett 377(2);217-20. PMID: 8543054

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Leon95: Leon J, Shulaev V, Yalpani N, Lawton MA, Raskin I (1995). "Benzoic acid 2-hydroxylase, a soluble oxygenase from tobacco, catalyzes salicylic acid biosynthesis." Proc Natl Acad Sci U S A 92(22);10413-7. PMID: 7479795

Long05: Long RM, Croteau R (2005). "Preliminary assessment of the C13-side chain 2'-hydroxylase involved in taxol biosynthesis." Biochem Biophys Res Commun 338(1);410-7. PMID: 16137660

Matsumura84: Matsumura M, Osada K, Aiba S (1984). "L-tryptophan 2,3-dioxygenase of a moderate thermophile, Bacillus brevis. Purification, properties and a substrate-mediated stabilization of the quaternary structure." Biochim Biophys Acta 786(1-2);9-17. PMID: 6712960

Meckenstock99: Meckenstock RU, Krieger R, Ensign S, Kroneck PM, Schink B (1999). "Acetylene hydratase of Pelobacter acetylenicus. Molecular and spectroscopic properties of the tungsten iron-sulfur enzyme." Eur J Biochem 1999;264(1);176-82. PMID: 10447686

Molog01: Molog GA, Empt U, Kuhlmann S, van Uden W, Pras N, Alfermann AW, Petersen M (2001). "Deoxypodophyllotoxin 6-hydroxylase, a cytochrome P450 monooxygenase from cell cultures of Linum flavum involved in the biosynthesis of cytotoxic lignans." Planta 214(2);288-94. PMID: 11800394

Nasreen96: Nasreen, A., Rueffer, M, Zenk, M.H (1996). "Cytochrome P-450-dependent fromation of isoandrocymbine from autumnaline in colchicine biosynthesis." tetrahedron Letters, 37, 8161-8164.

Ogishima87: Ogishima T, Deguchi S, Okuda K (1987). "Purification and characterization of cholesterol 7 alpha-hydroxylase from rat liver microsomes." J Biol Chem 262(16);7646-50. PMID: 3584134

Ohyama91: Ohyama Y, Okuda K (1991). "Isolation and characterization of a cytochrome P-450 from rat kidney mitochondria that catalyzes the 24-hydroxylation of 25-hydroxyvitamin D3." J Biol Chem 266(14);8690-5. PMID: 2026586

Okuda88: Okuda K, Masumoto O, Ohyama Y (1988). "Purification and characterization of 5 beta-cholestane-3 alpha,7 alpha,12 alpha-triol 27-hydroxylase from female rat liver mitochondria." J Biol Chem 263(34);18138-42. PMID: 2848026

Paulson85: Paulson SK, DeLuca HF (1985). "Subcellular location and properties of rat renal 25-hydroxyvitamin D3-1 alpha-hydroxylase." J Biol Chem 260(21);11488-92. PMID: 4044567

Peters98: Peters S, Schmidt W, Beerhues L (1998). "Regioselective oxidative phenol couplings of 2,3',4,6-tetrahydroxybenzophenone in cell cultures of Centaurium erythraea RAFN and Hypericum androsaemum L." Planta, 204: 64-69.

Rueffer98: Rueffer, M, Zenk, M.H (1998). "Microsome-mediated transformation of O-methylandrocymbine to demecolcine and colchicine." FEBS letters, 438, 111-113.

Sawers86: Sawers RG, Boxer DH (1986). "Purification and properties of membrane-bound hydrogenase isoenzyme 1 from anaerobically grown Escherichia coli K12." Eur J Biochem 1986;156(2);265-75. PMID: 3516689

Schlangen09: Schlangen K, Miosic S, Castro A, Freudmann K, Luczkiewicz M, Vitzthum F, Schwab W, Gamsjager S, Musso M, Halbwirth H (2009). "Formation of UV-honey guides in Rudbeckia hirta." Phytochemistry 70(7);889-98. PMID: 19477473

Schmidt00: Schmidt W, Peters S, Beerhues L (2000). "Xanthone 6-hydroxylase from cell cultures of Centaurium erythraea RAFN and Hypericum androsaemium L." Phytochemistry 53(4);427-31. PMID: 10731018

Schmidt97: Schmidt W, Beerhues L (1997). "Alternative pathways of xanthone biosynthesis in cell cultures of Hypericum androsaemum L." FEBS Lett 420(2-3);143-6. PMID: 9459298

Zumft75: Zumft WG, Mortenson LE (1975). "The nitrogen-fixing complex of bacteria." Biochim Biophys Acta 1975;416(1);1-52. PMID: 164247


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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