FComEx: Adenosylcobalamin (PC000667)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:51 UTC

Update date

2017-01-19 02:36:32 UTC

FoodComEx ID

PC000667

FoodDB Record

FDB022837

Chemical Information

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) [HMDB]

CAS Number

13870-90-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(5,6-Dimethylbenzimidazolyl)cobamide coenzyme	Kegg
(5'-Deoxy-5'-adenosyl)cobamide coenzyme	hmdb
5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamide	Kegg
5,6-Dimethylbenzimidazolyl-CO-5'-deoxy-5'-adenosylcobamide	Kegg
5'-Deoxy-5'-adenosyl vitamin B12	hmdb
5'-Deoxy-5'-adenosyl-5,6-dimethylbenzimidazolylcobamide	Kegg
5'-Deoxy-5'-adenosylcobalamin	hmdb
a-(5,6-Dimethylbenzimidazolyl)cobamide coenzyme	Generator
Adenosylcob(III)alamin	Kegg
Adenosylcobalamin 5'-ate	HMDB
Adenosylcobalamin 5'-phosphate	hmdb
alpha-(5,6-Dimethylbenzimidazolyl)cobamide coenzyme	Kegg
Calomide	hmdb
Cobalamin coenzyme	hmdb
Cobamamide	hmdb
Cobamamide 5'-ate	HMDB
Cobamamide 5'-phosphate	hmdb
Cobamide coenzyme	hmdb
Coenzyme B12	hmdb
Deoxyadenosylcobalamin	hmdb
Dibencozide	hmdb
DMBC coenzyme	Kegg
Funacomide	hmdb
vitamin B12 coenzyme	hmdb
Vitamin B12 coenzymes	hmdb
α-(5,6-dimethylbenzimidazolyl)cobamide coenzyme	Generator

Chemical Formula

C72H100CoN18O17P

IUPAC name

Not Available

InChI Identifier

InChI=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 Key

SWUYBPRJGLVABK-GONYIQIHSA-M

Isomeric SMILES

C1(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 Weight

1579.5818

Monoisotopic Molecular Weight

1578.65834557

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Corrinoids

Direct Parent

Cobalamin derivatives

Alternative Parents