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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:35 UTC
Update Date2017-10-23 19:03:56 UTC
HMDB IDHMDB0002086
Secondary Accession Numbers
  • HMDB02086
Metabolite Identification
Common 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 ).
Structure
Thumb
Synonyms
ValueSource
Adenosylcob(III)alaminKegg
DeoxyadenosylcobalaminKegg
CobamamideKegg
Vitamin b12 coenzymeKegg
5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamideKegg
(5'-Deoxy-5'-adenosyl)cobamide coenzymeKegg
(5,6-Dimethylbenzimidazolyl)cobamide coenzymeKegg
alpha-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeKegg
5'-Deoxy-5'-adenosylcobalaminKegg
5'-Deoxy-5'-adenosyl vitamin b12Kegg
5'-Deoxy-5'-adenosyl-5,6-dimethylbenzimidazolylcobamideKegg
5,6-Dimethylbenzimidazolyl-CO-5'-deoxy-5'-adenosylcobamideKegg
CalomideKegg
Cobalamin coenzymeKegg
Coenzyme b12Kegg
DMBC CoenzymeKegg
DibencozideKegg
FunacomideKegg
a-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeGenerator
α-(5,6-dimethylbenzimidazolyl)cobamide coenzymeGenerator
Adenosylcobalamin 5'-phosphateHMDB
Cobamamide 5'-phosphateHMDB
Cobamide coenzymeHMDB
Vitamin b12 coenzymesHMDB
Chemical FormulaC72H100CoN18O17P
Average Molecular Weight1579.5818
Monoisotopic Molecular Weight1578.65834557
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number13870-90-1
SMILES
C[C@@]12[C@H](C3N4C1=C(C1=[N]5C(=CC6=[N]7[Co+]45([N]4=CN(C5=C4C=C(C(C)=C5)C)[C@H]4O[C@H](CO)[C@@H](OP([O-])(O[C@@H](CNC(=O)CC2)C)=O)[C@H]4O)([N]2=C([C@H]([C@](C)(CC(=O)N)[C@]32C)CCC(=O)N)C(C)=C7[C@](C)([C@@H]6CCC(=O)N)CC(=O)N)C[C@@H]2[C@@H](O)[C@@H](O)[C@H](N3C4=C(C(N)=NC=N4)N=C3)O2)C([C@@H]1CCC(=O)N)(C)C)C)CC(N)=O
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-QRVZQHAISA-L
Chemical Taxonomy
DescriptionThis compound 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
  • 6-aminopurine
  • Benzimidazole
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Fatty amide
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Benzenoid
  • Imidolactam
  • Fatty acyl
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Pyrroline
  • Pyrrolidine
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • Lactam
  • Primary carboxylic acid amide
  • Azacycle
  • Organic metal salt
  • Organic transition metal salt
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carboxylic acid amidine
  • Carboxylic acid derivative
  • Oxacycle
  • Metalloheterocycle
  • Amidine
  • Primary alcohol
  • Organopnictogen compound
  • Organic cobalt salt
  • Organic oxide
  • Organic zwitterion
  • Organic nitrogen compound
  • Transition metal alkyl
  • Organic salt
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Amine
  • Organic transition metal moeity
  • Organometallic compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

Biological role:

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 Solubility0.069 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
Polarizability158.83 ųChemAxon
Number of Rings15ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencyPw000061Pw000061 greyscalePw000061 simpleNot Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencyPw000063Pw000063 greyscalePw000063 simpleNot Available
3-Methylcrotonyl Coa Carboxylase Deficiency Type IPw000065Pw000065 greyscalePw000065 simpleNot Available
3-Methylglutaconic Aciduria Type IPw000066Pw000066 greyscalePw000066 simpleNot Available
3-Methylglutaconic Aciduria Type IIIPw000067Pw000067 greyscalePw000067 simpleNot Available
Displaying entries 1 - 5 of 22 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022837
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00194
BioCyc IDADENOSYLCOBALAMIN-5-P
BiGG ID34204
Wikipedia LinkAdenosylcobalamin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID18408
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Moras E, Hosack A, Watkins D, Rosenblatt DS: Mitochondrial vitamin B12-binding proteins in patients with inborn errors of cobalamin metabolism. Mol Genet Metab. 2007 Feb;90(2):140-7. Epub 2006 Sep 29. [PubMed:17011224 ]

Enzymes

General function:
Involved in isomerase activity
Specific function:
Involved in the degradation of several amino acids, odd-chain fatty acids and cholesterol via propionyl-CoA to the tricarboxylic acid cycle. MCM has different functions in other species.
Gene Name:
MUT
Uniprot ID:
P22033
Molecular weight:
83133.755
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
MMAB
Uniprot ID:
Q96EY8
Molecular weight:
27387.975
General function:
Involved in nucleotide binding
Specific function:
Probable GTPase. May function as chaperone. May be involved in the transport of cobalamin (Cbl) into mitochondria for the final steps of adenosylcobalamin (AdoCbl) synthesis
Gene Name:
MMAA
Uniprot ID:
Q8IVH4
Molecular weight:
46537.9