Record Information
Version1.0
Creation date2011-09-21 00:20:22 UTC
Update date2015-10-09 22:31:51 UTC
Primary IDFDB022837
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAdenosylcobalamin
DescriptionAdenosylcobalamin is one of two metabolically active forms synthesized upon ingestion of vitamin B12 and is the predominant form in the liver; it acts as a coenzyme in the reaction catalyzed by methylmalonyl-CoA mutase. A cobalamin (cbl) derivative in which the substituent is deoxyadenosyl. It is one of two metabolically active forms synthesized upon ingestion of vitamin B12 and is the predominant form in the liver; it acts as a coenzyme in the reaction catalyzed by methylmalonyl-CoA mutase (MCM; E.C. 5.4.99.2). Inborn errors of vitamin B12 metabolism are autosomal recessive disorders and have been classified into nine distinct complementation classes. Disorders affecting adenosylcobalamin cause methylmalonic acidemia and metabolic acidosis. Methylmalonyl-CoA mutase catalyzes the conversion of L-methylmalonyl-CoA to succinyl-CoA and uses adenosylcobalamin (AdoCbl) as a cofactor. Cbl must be transported into mitochondria, reduced and adenosylated before it can be utilized by MCM. (PMID: 17011224) [HMDB]
CAS Number13870-90-1
Structure
Thumb
Synonyms
SynonymSource
(5,6-Dimethylbenzimidazolyl)cobamide coenzymeKegg
(5'-Deoxy-5'-adenosyl)cobamide coenzymehmdb
5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamideKegg
5,6-Dimethylbenzimidazolyl-CO-5'-deoxy-5'-adenosylcobamideKegg
5'-Deoxy-5'-adenosyl vitamin B12hmdb
5'-Deoxy-5'-adenosyl-5,6-dimethylbenzimidazolylcobamideKegg
5'-Deoxy-5'-adenosylcobalaminhmdb
a-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeGenerator
Adenosylcob(III)alaminKegg
Adenosylcobalamin 5'-ateHMDB
Adenosylcobalamin 5'-phosphatehmdb
alpha-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeKegg
Calomidehmdb
Cobalamin coenzymehmdb
Cobamamidehmdb
Cobamamide 5'-ateHMDB
Cobamamide 5'-phosphatehmdb
Cobamide coenzymehmdb
Coenzyme B12hmdb
Deoxyadenosylcobalaminhmdb
Dibencozidehmdb
DMBC coenzymeKegg
Funacomidehmdb
vitamin B12 coenzymehmdb
Vitamin B12 coenzymeshmdb
α-(5,6-dimethylbenzimidazolyl)cobamide coenzymeGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.069 g/LALOGPS
logP0.37ALOGPS
logS-4.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area598.55 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity408.83 m³·mol⁻¹ChemAxon
Polarizability158.25 ųChemAxon
Number of Rings15ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC72H100CoN18O17P
IUPAC name
InChI IdentifierInChI=1S/C62H89N13O14P.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,(H2,63,77)(H2,64,78)(H2,65,79)(H2,66,80)(H2,67,81)(H2,68,82)(H,69,83)(H,85,86);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q-1;;+2/p-1/b54-32-;;/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57+,59-,60+,61+,62+;4-,6-,7-,10-;/m11./s1
InChI KeySWUYBPRJGLVABK-GONYIQIHSA-M
Isomeric SMILESC1(C)(C)[C@]([H])(CCC(N)=O)C2=[N]3[Co+]456([N]7=CN([C@]8(O[C@]([H])(CO)[C@@](OP(O[C@@](C)([H])CNC(=O)CC[C@]9(C)[C@@](C([C@@]%10([N]4=C(C(=C4[C@](C)([C@]([H])(CCC(N)=O)C(=[N]54)C=C13)CC(N)=O)C)[C@@]([C@]%10(C)CC(N)=O)([H])CCC(N)=O)C)N6C9=C2C)([H])CC(N)=O)(=O)[O-])([C@]8(O)[H])[H])[H])C1=C7C=C(C)C(=C1)C)C[C@]1(O[C@]([C@@]([C@@]1(O)[H])(O)[H])(N1C=NC2=C1N=CN=C2N)[H])[H]
Average Molecular Weight1579.5818
Monoisotopic Molecular Weight1578.65834557
Classification
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassTetrapyrroles and derivatives
Direct ParentCobalamin derivatives
Alternative Parents
Substituents
  • Cobalamin
  • Metallotetrapyrrole skeleton
  • Pentose phosphate
  • 5'-deoxyribonucleoside
  • 6-aminopurine
  • Benzimidazole
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Primary aromatic amine
  • Fatty acyl
  • Imidolactam
  • Pyrimidine
  • Fatty amide
  • Benzenoid
  • Azole
  • Heteroaromatic compound
  • Pyrrolidine
  • Pyrroline
  • Imidazole
  • Oxolane
  • Amino acid or derivatives
  • Primary carboxylic acid amide
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Carboxylic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carboxylic acid amidine
  • Organic transition metal salt
  • Metalloheterocycle
  • Organic metal salt
  • Azacycle
  • Oxacycle
  • Amidine
  • Organic nitrogen compound
  • Organic transition metal moeity
  • Organometallic compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Primary amine
  • Organic zwitterion
  • Organic salt
  • Organic cobalt salt
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Transition metal alkyl
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 ID30791458
ChEMBL IDNot Available
KEGG Compound IDC00194
Pubchem Compound ID6436143
Pubchem Substance IDNot Available
ChEBI ID18408
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02086
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34204
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAdenosylcobalamin
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
Methylmalonyl-CoA mutase, mitochondrialMUTP22033
Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrialMMABQ96EY8
Methylmalonic aciduria type A protein, mitochondrialMMAAQ8IVH4
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference