Human Metabolome Database Version 3.5

Showing metabocard for Adenosylcobalamin (HMDB02086)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:35 -0600
Update Date 2013-07-24 11:53:32 -0600
HMDB ID HMDB02086
Secondary Accession Numbers None
Metabolite Identification
Common Name Adenosylcobalamin
Description Adenosylcobalamin 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C72H100CoN18O17P
Average Molecular Weight 1579.5818
Monoisotopic Molecular Weight 1578.65834557
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 IUPAC 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 Number 13870-90-1
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 Key ZIHHMGTYZOSFRC-QRVZQHAISA-L
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Terpene 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 Parent Diterpene Glycosides
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 0.37 ALOGPS
LogS -4.38 ALOGPS
Hydrogen Acceptor Count 0 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 598.55 A2 ChemAxon
Rotatable Bond Count 19 ChemAxon
Refractivity 408.83 ChemAxon
Polarizability 158.83 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022837
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C00194 Link_out
BioCyc ID ADENOSYLCOBALAMIN-5-P Link_out
BiGG ID 34204 Link_out
Wikipedia Link Adenosylcobalamin Link_out
NuGOwiki Link HMDB02086 Link_out
Metagene Link HMDB02086 Link_out
METLIN ID Not Available
PubChem Compound Not Available
PDB ID Not Available
ChEBI ID 18408 Link_out
References
Synthesis Reference Not 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 Link_out

Enzymes
Name: Methylmalonyl-CoA mutase, mitochondrial
Reactions: Not Available
Gene Name: MUT
Uniprot ID: P22033 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrial
Reactions: Not Available
Gene Name: MMAB
Uniprot ID: Q96EY8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Methylmalonic aciduria type A protein, mitochondrial
Reactions: Not Available
Gene Name: MMAA
Uniprot ID: Q8IVH4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA