MetaCyc Compound: cob(I)alamin

Synonyms: cobalamin, B12s

Superclasses: an organic heterocyclic compoundan organonitrogen heterocyclic compounda polypyrrolecyclic polypyrrolea cyclic tetrapyrrolea corrinoida cobalt-corrinoid hexaamidea cobamidea cobalamin
an organometallic compound

Cobalamin is the term used for a cobamide attached to a 5,6-dimethylbenzimidazole lower axial ligand of the cobalt ion, without specifying the upper axial ligand. It includes several compounds often referred to as vitamin B12, that differ in the upper axial ligand. The functional forms of the B12 vitamin, methylcob(III)alamin and adenosylcobalamin, include either a methyl group or an 5'-deoxyadenosyl group as their upper axial ligand, respectively.

Other forms of cobalamin include hydroxocobalamin (or its conjugated acid aquacobalamin) and cyanocob(III)alamin. Hydroxocobalamin is a naturally produced form synthesized by many bacterial species, while cyanocob(III)alamin is a common semi-synthetic form produced from bacterially-synthesized hydroxocobalamin. Vitamin B12 pills often contain cyanocob(III)alamin, which is converted to the active forms in the body.

The cobalt ion embedded in cobalamin may exist in different charges (+1, +2 or +3), and the different forms of the compound are referred to as cob(I)alamin, cob(II)alamin and cob(III)alamin, respectively.

Chemical Formula: C62H88N13O14PCo

Molecular Weight: 1329.4 Daltons

Monoisotopic Molecular Weight: 1329.5721563439001 Daltons

cob(I)alamin compound structure

SMILES: CC%10(=C(C)C=C9(N8(C%12(OC(CO)C(OP([O-])(=O)OC(C)CNC(=O)CCC1(C)(C(CC(N)=O)[CH]%11(C7(C)(C(C)(CC(N)=O)C(CCC(=O)N)C6(C(C)=C5(C(CC(=O)N)(C)C(CCC(N)=O)C4(C=C3(C(C)(C)C(CCC(N)=O)C2(C(C)=C1N([Co----]([N+]=23)([N+]=45)([N+]=67)[N+](=C8)C9=C%10)%11)))))))))C(O)%12))))

InChI: InChI=1S/C62H90N13O14P.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);/q;+1/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;/m1./s1


Unification Links: CAS:18534-66-2, ChEBI:15982, ChemSpider:4573816, HMDB:HMDB03429, IAF1260:36205, KEGG:C00853, MetaboLights:MTBLC15982, PubChem:5460183

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 478.9465Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

adenosylcobalamin salvage from cobalamin :
ATP + cob(I)alamin → adenosylcobalamin + PPPi

Reactions known to produce the compound:

Not in pathways:
cob(I)alamin + hydrogen cyanide + NADP+ ← cyanocob(III)alamin + NADPH

In Reactions of unknown directionality:

Not in pathways:
cob(I)alamin + S-adenosyl-L-methionine = methylcob(III)alamin + S-adenosyl-L-homocysteine
2 cob(I)alamin + NAD+ + H+ = 2 cob(II)alamin + NADH

In Transport reactions:
ATP + cob(I)alamin[periplasm] + H2O → ADP + cob(I)alamin[cytosol] + phosphate + H+,
cob(I)alamin[extracellular space]cob(I)alamin[cytosol],
cob(I)alamin[extracellular space]cob(I)alamin[periplasm],
a cobalamin[extracellular space] + ATP + H2O ↔ a cobalamin[cytosol] + ADP + phosphate

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: tetrachloroethene reductive dehalogenase, corrinoid protein:5-methyltetrahydrosarcinapterin methyltransferase

This compound has been characterized as an alternative substrate of the following enzymes: cob(I)yrinic acid a,c-diamide adenosyltransferase

Revised 22-Jul-2015 by Caspi R, SRI International


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Barker60a: Barker HA, Smyth RD, Weissbach H, Toohey JI, Ladd JN, Volcani BE (1960). "Isolation and properties of crystalline cobamide coenzymes containing benzimidazole or 5, 6-dimethylbenzimidazole." J Biol Chem 235;480-8. PMID: 13796809

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

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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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