Record Information
Version1.0
Creation date2015-10-09 22:31:51 UTC
Update date2017-01-19 02:36:32 UTC
FoodComEx IDPC000667
FoodDB RecordFDB022837
Chemical Information
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 coenzymeKegg
(5'-Deoxy-5'-adenosyl)cobamide coenzymehmdb
5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamideKegg
5,6-Dimethylbenzimidazolyl-CO-5'-deoxy-5'-adenosylcobamideKegg
5'-Deoxy-5'-adenosyl vitamin B12hmdb
5'-Deoxy-5'-adenosyl-5,6-dimethylbenzimidazolylcobamideKegg
5'-Deoxy-5'-adenosylcobalaminhmdb
a-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeGenerator
Adenosylcob(III)alaminKegg
Adenosylcobalamin 5'-ateHMDB
Adenosylcobalamin 5'-phosphatehmdb
alpha-(5,6-Dimethylbenzimidazolyl)cobamide coenzymeKegg
Calomidehmdb
Cobalamin coenzymehmdb
Cobamamidehmdb
Cobamamide 5'-ateHMDB
Cobamamide 5'-phosphatehmdb
Cobamide coenzymehmdb
Coenzyme B12hmdb
Deoxyadenosylcobalaminhmdb
Dibencozidehmdb
DMBC coenzymeKegg
Funacomidehmdb
vitamin B12 coenzymehmdb
Vitamin B12 coenzymeshmdb
α-(5,6-dimethylbenzimidazolyl)cobamide coenzymeGenerator
Chemical FormulaNot Available
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
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
Chemical Taxonomy
ClassificationNot classified
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
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
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci V0102
Cayman Chemical 21571
Toronto Research Chemicals C633130