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Record Information
Version3.6
Creation Date2006-05-22 14:17:35 UTC
Update Date2013-07-24 17:53:32 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
  1. (5'-Deoxy-5'-adenosyl)cobamide coenzyme
  2. 5'-Deoxy-5'-adenosyl vitamin B12
  3. 5'-Deoxy-5'-adenosylcobalamin
  4. Adenosylcobalamin 5'-phosphate
  5. Calomide
  6. Cobalamin coenzyme
  7. Cobamamide
  8. Cobamamide 5'-phosphate
  9. Cobamide coenzyme
  10. Coenzyme B12
  11. Deoxyadenosylcobalamin
  12. Dibencozide
  13. Funacomide
  14. Vitamin B12 coenzyme
  15. Vitamin B12 coenzymes
Chemical FormulaC72H100CoN18O17P
Average Molecular Weight1579.5818
Monoisotopic Molecular Weight1578.65834557
IUPAC Name(10S,12R,13S,17R,23R,24R,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-2$l^{4},9,19,26,43$l^{4},44$l^{4},45$l^{4}-heptaaza-15$l^{5}-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(8),4,6,27,29(44),32,34(45),37,39(43)-decaen-1-ylium-15-olate
Traditional Name(10S,12R,13S,17R,23R,24R,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-unde
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
KingdomOrganic Compounds
Super ClassLipids
ClassPrenol Lipids
Sub ClassTerpene Glycosides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Purine Nucleosides and Analogues
Substituents
  • 1,2 Diol
  • Aminopyrimidine
  • Benzimidazole
  • Carboxamide Group
  • Corrin
  • Diterpene
  • Enamine
  • Imidazole
  • Imidazopyrimidine
  • Imine
  • Lactam
  • Metallotetrapyrrole Skeleton
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Transition Metal Moeity
  • Organometallic Compound
  • Oxolane
  • Phosphoric Acid Ester
  • Primary Alcohol
  • Primary Carboxylic Acid Amide
  • Purine
  • Pyrimidine
  • Pyrrolidine
  • Pyrroline
  • Quaternary Ammonium Salt
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Tetrapyrrole Skeleton
  • Toluene
Direct ParentDiterpene Glycosides
Ontology
StatusExpected and 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 Solubility0.069ALOGPS
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
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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. 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