Record Information
Creation date2015-10-09 22:31:51 UTC
Update date2017-01-19 02:36:32 UTC
FoodComEx IDPC000667
FoodDB RecordFDB022837
Chemical Information
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. 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
(5,6-Dimethylbenzimidazolyl)cobamide coenzymeKegg
(5'-Deoxy-5'-adenosyl)cobamide coenzymehmdb
5'-Deoxy-5'-adenosyl vitamin B12hmdb
a-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeGenerator
Adenosylcobalamin 5'-ateHMDB
Adenosylcobalamin 5'-phosphatehmdb
alpha-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeKegg
Cobalamin coenzymehmdb
Cobamamide 5'-ateHMDB
Cobamamide 5'-phosphatehmdb
Cobamide coenzymehmdb
Coenzyme B12hmdb
DMBC coenzymeKegg
vitamin B12 coenzymehmdb
Vitamin B12 coenzymeshmdb
α-(5,6-dimethylbenzimidazolyl)cobamide coenzymeGenerator
Chemical FormulaC72H100CoN18O17P
IUPAC nameNot Available
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
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
Chemical Taxonomy
Description 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
  • 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
Physico-Chemical Properties - Experimental
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 10 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez
Commercial Vendors
AKSci V0102
Cayman Chemical 21571
Toronto Research Chemicals C633130