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Record Information
Version3.6
Creation Date2006-05-22 14:17:35 UTC
Update Date2016-02-11 01:05:16 UTC
HMDB IDHMDB02086
Secondary Accession NumbersNone
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 KeyInChIKey=ZIHHMGTYZOSFRC-QRVZQHAISA-L
Chemical Taxonomy
ClassificationNot classified
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
Water Solubility0.069 mg/mLALOGPS
logP0.37ALOGPS
logS-4.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area598.55 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity408.83 m3·mol-1ChemAxon
Polarizability158.83 Å3ChemAxon
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 LinkKEGG Link
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencySMP00137Not Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencySMP00138Not Available
3-hydroxyisobutyric acid dehydrogenase deficiencySMP00521Not Available
3-hydroxyisobutyric aciduriaSMP00522Not Available
3-Methylcrotonyl Coa Carboxylase Deficiency Type ISMP00237Not Available
3-Methylglutaconic Aciduria Type ISMP00139Not Available
3-Methylglutaconic Aciduria Type IIISMP00140Not Available
3-Methylglutaconic Aciduria Type IVSMP00141Not Available
Beta-Ketothiolase DeficiencySMP00173Not Available
Isobutyryl-coa dehydrogenase deficiencySMP00523Not Available
Isovaleric acidemiaSMP00524Not Available
Isovaleric AciduriaSMP00238Not Available
Malonic AciduriaSMP00198Not Available
Malonyl-coa decarboxylase deficiencySMP00502Not Available
Maple Syrup Urine DiseaseSMP00199Not Available
Methylmalonate Semialdehyde Dehydrogenase DeficiencySMP00384Not Available
Methylmalonic AciduriaSMP00200Not Available
Methylmalonic Aciduria Due to Cobalamin-Related DisordersSMP00201Not Available
Propanoate MetabolismSMP00016map00640
Propionic AcidemiaSMP00236Not Available
Threonine and 2-Oxobutanoate DegradationSMP00452Not Available
Valine, Leucine and Isoleucine DegradationSMP00032map00280
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
NuGOwiki LinkHMDB02086
Metagene LinkHMDB02086
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. [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