Record Information
Version1.0
Creation date2011-04-11 17:01:50 UTC
Update date2019-11-26 03:20:55 UTC
Primary IDFDB021826
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number18534-66-2
Structure
Thumb
Synonyms
SynonymSource
Hydrido-cobalaminHMDB
HydridocobalaminHMDB
Vitamin b12SHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.077 g/LALOGPS
logP2.54ALOGPS
logS-4.2ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area462.6 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity409.42 m³·mol⁻¹ChemAxon
Polarizability134.19 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC62H88CoN13O14P
IUPAC namelambda2-cobalt(2+) ion 3-[13-(3-azanidyl-3-oxopropyl)-4-{2-[(2-{[hydroxy({[4-hydroxy-2-(hydroxymethyl)-5-(5-methyl-1-methylidene-3H-1lambda5,3-benzodiazol-3-yl)oxolan-3-yl]oxy})phosphoryl]oxy}propyl)-C-hydroxycarbonimidoyl]ethyl}-18-[2-(C-hydroxycarbonimidoyl)ethyl]-3,14,19-tris[(C-hydroxycarbonimidoyl)methyl]-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]tricosa-5(23),6,10(22),11,15(21),16-hexaen-8-yl]propanecarboximidate
InChI IdentifierInChI=1S/C62H90N13O14P.Co/c1-30-12-16-39-40(22-30)75(29-74(39)11)57-52(84)53(41(28-76)87-57)89-90(85,86)88-31(2)27-69-49(83)20-21-59(7)37(23-46(66)80)56-62(10)61(9,26-48(68)82)36(15-19-45(65)79)51(73-62)33(4)55-60(8,25-47(67)81)34(13-17-43(63)77)38(70-55)24-42-58(5,6)35(14-18-44(64)78)50(71-42)32(3)54(59)72-56;/h12,16,22,24,29,31,34-37,41,52-53,56-57,76,84H,11,13-15,17-21,23,25-28H2,1-10H3,(H15,63,64,65,66,67,68,69,70,71,72,73,77,78,79,80,81,82,83,85,86);/q;+2/p-2
InChI KeyAQRVTLGDEBVZBZ-UHFFFAOYSA-L
Isomeric SMILESCC1CNC(=O)CCC2(C)C(CC(N)=O)C3[N]4=C2C(C)=C2C(CCC(N)=O)C(C)(C)C5=[N]2[Co+]42(C[N]4=CN(C6OC(CO)C(OP([O-])(=O)O1)C6O)C1=CC(C)=CC=C41)N1C(C(CCC(N)=O)C(C)(CC(N)=O)C31C)=C(C)C1=[N]2C(=C5)C(CCC(N)=O)C1(C)CC(N)=O
Average Molecular Weight1329.3478
Monoisotopic Molecular Weight1328.564331295
Classification
Description Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGuaianolides and derivatives
Alternative Parents
Substituents
  • Guaianolide-skeleton
  • Guaiane sesquiterpenoid
  • Sesquiterpenoid
  • Gamma butyrolactone
  • Oxane
  • Cyclic alcohol
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC00853
Pubchem Compound ID53477772
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03429
CRC / DFC (Dictionary of Food Compounds) IDGLB45-G:GLB45-G
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36205
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrialMMABQ96EY8
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference