Showing metabocard for Adenosylcobalamin (BMDB0002086)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:51:01 UTC
Update Date2020-04-22 15:09:42 UTC
BMDB IDBMDB0002086
Secondary Accession Numbers
  • BMDB02086
Metabolite Identification
Common NameAdenosylcobalamin
DescriptionAdenosylcobalamin, also known as cobamamid or coenzyme b-12, 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. Adenosylcobalamin is a strong basic compound (based on its pKa). Adenosylcobalamin is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5,6-Dimethylbenzimidazolyl)cobamide coenzymeChEBI
5'-Deoxy-5'-adenosyl vitamin b12ChEBI
5'-Deoxy-5'-adenosyl-5,6-dimethylbenzimidazolylcobamideChEBI
5'-Deoxy-5'-adenosylcobalaminChEBI
5'-Deoxyadenosyl vitamin b12ChEBI
5'-Deoxyadenosyl-5,6-dimethylbenzimidazolylcobamideChEBI
5'-DeoxyadenosylcobalaminChEBI
5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamideChEBI
5,6-Dimethylbenzimidazolyl-CO-5'-deoxy-5'-adenosylcobamideChEBI
Adenosylcob(III)alaminChEBI
AdoCblChEBI
alpha-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeChEBI
CalomideChEBI
Coalpha-[alpha-(5,6-dimethylbenzimidazolyl)]-cobeta-adenosylcobamideChEBI
Cobalamin coenzymeChEBI
CobamamidChEBI
CobamamidaChEBI
CobamamidumChEBI
Cobamide coenzymeChEBI
Coenzyme b-12ChEBI
Coenzyme b12ChEBI
DBC CoenzymeChEBI
DeoxyadenosylcobalaminChEBI
DibencozideChEBI
DMBC CoenzymeChEBI
FunacomideChEBI
Vitamin b12 coenzymeChEBI
a-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeGenerator
Α-(5,6-dimethylbenzimidazolyl)cobamide coenzymeGenerator
Coalpha-[a-(5,6-dimethylbenzimidazolyl)]-cobeta-adenosylcobamideGenerator
Coalpha-[α-(5,6-dimethylbenzimidazolyl)]-cobeta-adenosylcobamideGenerator
Chemical FormulaC72H100CoN18O17P
Average Molecular Weight1579.5818
Monoisotopic Molecular Weight1578.65834557
IUPAC Name(10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-1-{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-46-hydroxy-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[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),3,5,7,27,29(44),32,34(45),37,39(43)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1-triuid-15-olate
Traditional Name(10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-1-{[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-46-hydroxy-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[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),3,5,7,27,29(44),32,34(45),37,39(43)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1-triuid-15-olate
CAS Registry Number13870-90-1
SMILES
[C@H]1(C[Co-3]2345[N+]6=C7C(C)=C8N2[C@]([H])([C@H](CC(=O)N)[C@]8(CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@@H]2[C@@H](CO)O[C@H](N8C=[N+]3C3=CC(C)=C(C)C=C83)[C@@H]2O)C)[C@@]2(C)[C@@](CC(=O)N)([C@H](CCC(=O)N)C(C(C)=C3[N+]4=C(C=C6C([C@@H]7CCC(=O)N)(C)C)[C@@H](CCC(=O)N)[C@@]3(CC(=O)N)C)=[N+]52)C)O[C@@H](N2C3=NC=NC(=C3N=C2)N)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C62H90N13O14P.C10H12N5O3.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;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/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);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1
InChI KeyZIHHMGTYZOSFRC-OUCXYWSSSA-L
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
Substituents
  • Cobalamin
  • Metallotetrapyrrole skeleton
  • Pentose phosphate
  • 5'-deoxyribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Purine
  • Imidazopyrimidine
  • Benzimidazole
  • Aminopyrimidine
  • Organic phosphoric acid derivative
  • Pyrimidine
  • N-substituted imidazole
  • Monosaccharide
  • Benzenoid
  • Fatty amide
  • Imidolactam
  • Fatty acyl
  • Azole
  • Pyrroline
  • Imidazole
  • Heteroaromatic compound
  • Pyrrolidine
  • Tetrahydrofuran
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Organic transition metal salt
  • Azacycle
  • Carboxylic acid derivative
  • Organic metal salt
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Oxacycle
  • Metalloheterocycle
  • Primary amine
  • Transition metal alkyl
  • Organic zwitterion
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic transition metal moeity
  • Carbonyl group
  • Organic salt
  • Organometallic compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Amine
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-15ChemAxon
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area536.31 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity397.85 m³·mol⁻¹ChemAxon
Polarizability156.67 ųChemAxon
Number of Rings15ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
  • Mitochondria
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002086
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022837
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDADENOSYLCOBALAMIN
BiGG IDNot Available
Wikipedia LinkCobamamide
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID18408
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available