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Record Information
Version3.6
Creation Date2006-08-12 20:37:00 UTC
Update Date2013-07-24 17:54:41 UTC
HMDB IDHMDB03429
Secondary Accession Numbers
  • HMDB06470
Metabolite Identification
Common NameCob(I)alamin
DescriptionCob(I)alamin is the substrate of the enzyme ATP:cob(I)alamin adenosyltransferase (EC 2.5.1.17), that converts reduced cob(I)alamin to the adenosylcobalamin co-factor required for the functional activity of methylmalonyl-CoA mutase (EC 5.4.99.2). 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. 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 ).
Structure
Thumb
Synonyms
  1. Cob(I)alamin
  2. Cyanocobalamin
  3. Hydrido-Cobalamin
  4. Hydridocobalamin
  5. Vitamin B12s
Chemical FormulaC62H88CoN13O14P
Average Molecular Weight1329.3478
Monoisotopic Molecular Weight1328.564331295
IUPAC Name3-[(12S,23R,24R,30S,35S,36S,40S,41S,42R)-30,35-bis(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-2$l^{4},9,19,26$l^{4},43$l^{4},44$l^{4},45$l^{4}-heptaaza-15$l^{5}-phospha-1-cobaltadodecacyclo[27.14.1.1^{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(8),4,6,25,27,29(44),32,34(45),37,39(43)-undecaen-40-yl]propanamide
Traditional IUPAC Name3-[(12S,23R,24R,30S,35S,36S,40S,41S,42R)-30,35-bis(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-2$l^{4},9,19,26$l^{4},43$l^{4},44$l^{4},45$l^{4}
CAS Registry Number18534-66-2
SMILES
CC1CNC(=O)CC[C@]2(C)[C@@H](CC(N)=O)C3=[N]4C2=C(C)C2=[N]5C(=CC6=[N]7C(=C(C)C8=[N]([C@]3(C)[C@@](C)(CC(N)=O)[C@@H]8CCC(N)=O)[Co]457[N]3=CN(C4O[C@@H](CO)C(OP(O)(=O)O1)C4O)C1=C3C=C(C)C(C)=C1)[C@@](C)(CC(N)=O)[C@@H]6CCC(N)=O)C(C)(C)[C@@H]2CCC(N)=O
InChI Identifier
InChI=1S/C62H88N13O14P.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;/h20-21,23,28,31,34-37,41,52-53,57,76,84H,12-19,22,24-27H2,1-11H3,(H2,63,77)(H2,64,78)(H2,65,79)(H2,66,80)(H2,67,81)(H2,68,82)(H,69,83)(H,85,86);/b42-23-,54-32-,55-33-;/t31?,34-,35-,36-,37+,41+,52?,53?,57?,59-,60+,61+,62+;/m1./s1
InChI KeySJBNFITWNDPBKE-WJICPROSSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassTetrapyrroles and Derivatives
Sub ClassMetallotetrapyrroles
Other Descriptors
  • Organic Compounds
Substituents
  • Benzimidazole
  • Carboxamide Group
  • Diterpene
  • Imidazole
  • Imine
  • Lactam
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Transition Metal Moeity
  • Organometallic Compound
  • Oxolane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Primary Carboxylic Acid Amide
  • Pyrroline
  • Quaternary Ammonium Salt
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Toluene
Direct ParentMetallotetrapyrroles
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.045 g/LALOGPS
logP1.04ALOGPS
logS-4.5ALOGPS
physiological charge0ChemAxon
hydrogen acceptor count0ChemAxon
hydrogen donor count0ChemAxon
polar surface area492.38ChemAxon
rotatable bond count16ChemAxon
refractivity352.19ChemAxon
polarizability134.58ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0003 (0.00016-0.0005) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00041 (0.00015-0.00067) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000094 (0.000037-0.00015) uMChildren (1-13 years old)BothCobalamin malabsorption details
Associated Disorders and Diseases
Disease References
Cobalamin malabsorption
  1. MetaGene
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021826
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00853
BioCyc IDCOB-I-ALAMIN
BiGG ID36205
Wikipedia LinkCyanocobalamin
NuGOwiki LinkHMDB03429
Metagene LinkHMDB03429
METLIN IDNot Available
PubChem Compound53477772
PDB IDNot Available
ChEBI ID15982
References
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

Enzymes

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:
MTR
Uniprot ID:
Q99707
Molecular weight:
140525.91
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:
MTRR
Uniprot ID:
Q9UBK8
Molecular weight:
77672.995
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
MMAB
Uniprot ID:
Q96EY8
Molecular weight:
27387.975