MetaCyc Compound: carbon monoxide

Synonyms: CO, carbon monooxide

Chemical Formula: CO

Molecular Weight: 29.018 Daltons

Monoisotopic Molecular Weight: 29.0027396542 Daltons

carbon monoxide compound structure

SMILES: [C-]#[O+]

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


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

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

Reactions known to consume the compound:

carbon tetrachloride degradation II , hydrogen production VI :
carbon monoxide + an oxidized unknown electron acceptor + H2O → CO2 + an reduced unknown 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 I , phycoerythrobilin biosynthesis II , phycourobilin biosynthesis , phycoviolobilin biosynthesis , phytochromobilin biosynthesis :
ferroheme b + 3 a reduced [NADPH-hemoprotein reductase] + 3 oxygen + 2 H+ → biliverdin-IX-α + Fe2+ + carbon monoxide + 3 an oxidized [NADPH-hemoprotein reductase] + 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 an reduced unknown electron acceptor + 4 oxygen + 2 H+ → 15-oxo-β-bilirubin + Fe2+ + carbon monoxide + 4 an oxidized unknown electron acceptor + 4 H2O
ferroheme b + 4 an reduced unknown electron acceptor + 4 oxygen + 2 H+ → 5-oxo-δ-bilirubin + Fe2+ + carbon monoxide + 4 an oxidized unknown 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] + H+carbon monoxide + a [methyl-Co(III) corrinoid Fe-S protein] + coenzyme A
carbon monoxide + 2 an oxidized ferredoxin [iron-sulfur] cluster + H2O ↔ CO2 + 2 a reduced ferredoxin [iron-sulfur] cluster + 2 H+

reductive acetyl coenzyme A pathway :
acetyl-CoA + a [Co(I) corrinoid Fe-S protein] + H+carbon monoxide + a [methyl-Co(III) corrinoid Fe-S protein] + coenzyme A
carbon monoxide + 2 an oxidized ferredoxin [iron-sulfur] cluster + H2O ↔ CO2 + 2 a reduced ferredoxin [iron-sulfur] cluster + 2 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[periplasm]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: hydrogen:menaquinone oxidoreductase [Sawers86], nitric oxide dioxygenase [Gardner00, TinajeroTrejo14], (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]


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

Gardner00: Gardner PR, Gardner AM, Martin LA, Dou Y, Li T, Olson JS, Zhu H, Riggs AF (2000). "Nitric-oxide dioxygenase activity and function of flavohemoglobins. sensitivity to nitric oxide and carbon monoxide inhibition." J Biol Chem 275(41);31581-7. PMID: 10922365

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

TinajeroTrejo14: Tinajero-Trejo M, Denby KJ, Sedelnikova SE, Hassoubah SA, Mann BE, Poole RK (2014). "Carbon monoxide-releasing molecule-3 (CORM-3; Ru(CO)3Cl(glycinate)) as a tool to study the concerted effects of carbon monoxide and nitric oxide on bacterial flavohemoglobin Hmp: applications and pitfalls." J Biol Chem 289(43);29471-82. PMID: 25193663

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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