Record Information
Version1.0
Creation date2011-09-21 00:20:22 UTC
Update date2015-10-09 22:31:51 UTC
Primary IDFDB022837
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number13870-90-1
Structure
Thumb
Synonyms
SynonymSource
(5,6-Dimethylbenzimidazolyl)cobamide coenzymeChEBI
5'-Deoxy-5'-adenosyl vitamin b12ChEBI
5'-Deoxy-5'-adenosyl-5,6-dimethylbenzimidazolylcobamideChEBI
5'-Deoxy-5'-adenosylcobalaminChEBI
5'-Deoxyadenosyl vitamin b12ChEBI
5'-Deoxyadenosyl-5,6-dimethylbenzimidazolylcobamideChEBI
5'-DeoxyadenosylcobalaminChEBI
5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamideChEBI
5,6-Dimethylbenzimidazolyl-CO-5'-deoxy-5'-adenosylcobamideChEBI
Adenosylcob(III)alaminChEBI
AdoCblChEBI
alpha-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeChEBI
CalomideChEBI
Coalpha-[alpha-(5,6-dimethylbenzimidazolyl)]-cobeta-adenosylcobamideChEBI
Cobalamin coenzymeChEBI
CobamamidChEBI
CobamamidaChEBI
CobamamidumChEBI
Cobamide coenzymeChEBI
Coenzyme b-12ChEBI
Coenzyme b12ChEBI
DBC CoenzymeChEBI
DeoxyadenosylcobalaminChEBI
DibencozideChEBI
DMBC CoenzymeChEBI
FunacomideChEBI
Vitamin b12 coenzymeChEBI
a-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeGenerator
Α-(5,6-dimethylbenzimidazolyl)cobamide coenzymeGenerator
Coalpha-[a-(5,6-dimethylbenzimidazolyl)]-cobeta-adenosylcobamideGenerator
Coalpha-[α-(5,6-dimethylbenzimidazolyl)]-cobeta-adenosylcobamideGenerator
(5'-Deoxy-5'-adenosyl)cobamide coenzymehmdb
5'-Deoxy-5'-adenosyl vitamin B12hmdb
Adenosylcobalamin 5'-ateHMDB
Adenosylcobalamin 5'-phosphatehmdb
Cobamamidehmdb
Cobamamide 5'-ateHMDB
Cobamamide 5'-phosphatehmdb
Coenzyme B12hmdb
DMBC coenzymeKegg
vitamin B12 coenzymehmdb
Vitamin B12 coenzymeshmdb
α-(5,6-dimethylbenzimidazolyl)cobamide coenzymeGenerator
Predicted Properties
PropertyValueSource
logP-15ChemAxon
pKa (Strongest Acidic)1.81ChemAxon
pKa (Strongest Basic)3.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area536.31 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity397.85 m³·mol⁻¹ChemAxon
Polarizability156.67 ųChemAxon
Number of Rings15ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC72H100CoN18O17P
IUPAC name(10S,12R,13S,17R,23R,24R,25R,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-2lambda5,9,19,26,43lambda5,44lambda5,45lambda5-heptaaza-15lambda5-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),3,5,7,27,29(44),32,34(45),37,39(43)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1-triuid-15-olate
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
InChI KeySWUYBPRJGLVABK-GONYIQIHSA-M
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
Classification
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
Substituents
  • Cobalamin
  • Metallotetrapyrrole skeleton
  • Pentose phosphate
  • 5'-deoxyribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Purine
  • Imidazopyrimidine
  • Benzimidazole
  • Aminopyrimidine
  • Organic phosphoric acid derivative
  • Pyrimidine
  • N-substituted imidazole
  • Monosaccharide
  • Benzenoid
  • Fatty amide
  • Imidolactam
  • Fatty acyl
  • Azole
  • Pyrroline
  • Imidazole
  • Heteroaromatic compound
  • Pyrrolidine
  • Tetrahydrofuran
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Organic transition metal salt
  • Azacycle
  • Carboxylic acid derivative
  • Organic metal salt
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Oxacycle
  • Metalloheterocycle
  • Primary amine
  • Transition metal alkyl
  • Organic zwitterion
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic transition metal moeity
  • Carbonyl group
  • Organic salt
  • Organometallic compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Amine
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID30791458
ChEMBL IDNot Available
KEGG Compound IDC00194
Pubchem Compound ID6436143
Pubchem Substance IDNot Available
ChEBI ID18408
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02086
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34204
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAdenosylcobalamin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Methylmalonyl-CoA mutase, mitochondrialMUTP22033
Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrialMMABQ96EY8
Methylmalonic aciduria type A protein, mitochondrialMMAAQ8IVH4
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference