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Record Information
StatusDetected and Quantified
Creation Date2006-08-12 20:37:00 UTC
Update Date2020-02-26 21:24:36 UTC
Secondary Accession Numbers
  • HMDB0006470
  • HMDB03429
  • HMDB06470
Metabolite Identification
Common NameCob(I)alamin
DescriptionCob(I)alamin is the substrate of the enzyme ATP:cob(I)alamin adenosyltransferase (EC, that converts reduced cob(I)alamin to the adenosylcobalamin co-factor required for the functional activity of methylmalonyl-CoA mutase (EC Mutations in the human MMAB gene result in a block in adenosylcobalamin synthesis and are responsible for the cblB complementation group of inherited vitamin B12 disorders, such as cobalamin malabsorption, which is an inborn error of metabolism. Vitamin B12 (cobalamin) is a complex cobalt-containing molecule that is essential to human health. It is synthesized in bacteria where it catalyzes numerous methyl transfer and intramolecular rearrangement reactions. In mammals, it is the co-factor of only two enzymes: methionine synthase, which catalyzes the transfer of a methyl group from methyltetrahydrofolate to homocysteine to form methionine, and methylmalonyl-CoA mutase, which catalyzes the rearrangement of methylmalonyl-CoA to form succinyl-CoA. For both enzymes, the vitamin must be modified through intracellular metabolism to co-factor forms: methylcobalamin (MeCbl)1 for methionine synthase and adenosylcobalamin (AdoCbl) for methylmalonyl-CoA mutase (PMID: 16439175 ).
Vitamin b-12SChEBI
Vitamin b12SChEBI
Chemical FormulaC62H89CoN13O14P
Average Molecular Weight1330.378
Monoisotopic Molecular Weight1329.572151
IUPAC Name(10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-15,46-dihydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2lambda5,9,19,26,43lambda5,44lambda5,45lambda5-heptaaza-15lambda5-phospha-1-cobaltadodecacyclo[^{1,34}.1^{2,9}.1^{10,13}.0^{1,26}.0^{3,8}.0^{23,27}.0^{25,42}.0^{32,44}.0^{39,43}.0^{37,45}]heptatetraconta-2(47),3,5,7,27,29(44),32,34(45),37,39(43)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1,1-tetrauide
Traditional Name(10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-15,46-dihydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2lambda5,9,19,26,43lambda5,44lambda5,45lambda5-heptaaza-15lambda5-phospha-1-cobaltadodecacyclo[^{1,34}.1^{2,9}.1^{10,13}.0^{1,26}.0^{3,8}.0^{23,27}.0^{25,42}.0^{32,44}.0^{39,43}.0^{37,45}]heptatetraconta-2(47),3,5,7,27,29(44),32,34(45),37,39(43)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1,1-tetrauide
CAS Registry Number18534-66-2
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as cobalamin derivatives. These are organic compounds containing a corrin ring, a cobalt atom, an a nucleotide moiety. Cobalamin Derivatives are actually derived from vitamin B12.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassCorrinoids
Direct ParentCobalamin derivatives
Alternative Parents
  • Cobalamin
  • Metallotetrapyrrole skeleton
  • 1-ribofuranosylbenzimidazole
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Benzimidazole
  • Dialkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Pyrrolidine
  • Pyrroline
  • Tetrahydrofuran
  • Secondary alcohol
  • Ketimine
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid
  • Secondary amine
  • Carboximidic acid derivative
  • Secondary aliphatic amine
  • Enamine
  • Oxacycle
  • Azacycle
  • Organic transition metal salt
  • Organic 1,3-dipolar compound
  • Primary alcohol
  • Imine
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic zwitterion
  • Organic oxygen compound
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic cobalt salt
  • Organic salt
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physiological effect

Health effect:


Biological location:


Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.045 g/LALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)-0.55ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area414.17 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity338.59 m³·mol⁻¹ChemAxon
Polarizability134.39 ųChemAxon
Number of Rings12ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q0-0097000000-0021927d06a72e6704c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xu-0093000000-2a92353bd428991e480fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-0090000000-93430347c6ecec5d8cd3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01ti-0089000000-f49f5ec60e91e3af0114Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-1094000000-2defa0906339d10ef64dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-8092000000-345ba89e7a43d9592f0fSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Normal Concentrations
BloodDetected and Quantified0.0003 (0.00016-0.0005) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.000150-0.000400 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.000407 (0.000336-0.000540) uMChildren (1 - 13 years old)BothNormal details
Abnormal Concentrations
BloodDetected and Quantified0.00041 (0.00015-0.00067) uMAdult (>18 years old)BothCobalamin malabsorption
    • MetaGene: Metabol...
BloodDetected and Quantified0.000094 (0.000037-0.00015) uMChildren (1-13 years old)BothCobalamin malabsorption
    • MetaGene: Metabol...
BloodDetected and Quantified0.000222 uMAdult (>18 years old)MaleDimethylglycinuria details
Associated Disorders and Diseases
Disease References
Cobalamin malabsorption
  1. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: METAGENE consortium.
Dimethylglycine Dehydrogenase Deficiency
  1. Moolenaar SH, Poggi-Bach J, Engelke UF, Corstiaensen JM, Heerschap A, de Jong JG, Binzak BA, Vockley J, Wevers RA: Defect in dimethylglycine dehydrogenase, a new inborn error of metabolism: NMR spectroscopy study. Clin Chem. 1999 Apr;45(4):459-64. [PubMed:10102904 ]
Associated OMIM IDs
  • 605850 (Dimethylglycine Dehydrogenase Deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021826
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00853
BioCyc IDNot Available
BiGG ID36205
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477772
PDB IDNot Available
ChEBI ID15982
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhang J, Dobson CM, Wu X, Lerner-Ellis J, Rosenblatt DS, Gravel RA: Impact of cblB mutations on the function of ATP:cob(I)alamin adenosyltransferase in disorders of vitamin B12 metabolism. Mol Genet Metab. 2006 Apr;87(4):315-22. Epub 2006 Jan 24. [PubMed:16439175 ]


General function:
Involved in cobalamin binding
Specific function:
Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in oxidoreductase activity
Specific function:
Involved in the reductive regeneration of cob(I)alamin cofactor required for the maintenance of methionine synthase in a functional state.
Gene Name:
Uniprot ID:
Molecular weight:
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
Uniprot ID:
Molecular weight: