CHEBI:18408 - cobamamide

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ChEBI Name cobamamide
ChEBI ID CHEBI:18408
Definition A member of the class of cobalamins that is vitamin B12 in which the cyano group is replaced by a 5'-deoxyadenos-5'-yl moiety. It is one of the two metabolically active form of vitamin B12.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:13739, CHEBI:23340, CHEBI:3797
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Formula C72H100CoN18O17P
Net Charge 0
Average Mass 1579.58180
Monoisotopic Mass 1578.65834
InChI 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
InChIKey ZIHHMGTYZOSFRC-OUCXYWSSSA-L
SMILES [H][C@]12[C@H](CC(N)=O)[C@@]3(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@@H]4[C@@H](CO)O[C@@H]([C@@H]4O)n4c[n+](c5cc(C)c(C)cc45)[Co-3]456(C[C@H]7O[C@H]([C@H](O)[C@@H]7O)n7cnc8c(N)ncnc78)N1C3=C(C)C1=[N+]4C(=CC3=[N+]5C(=C(C)C4=[N+]6[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)C(C)(C)[C@@H]1CCC(N)=O
Metabolite of Species Details
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
coenzyme
A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
cofactor
An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group).
(via corrinoid )
prosthetic group
A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
water-soluble vitamin (role)
Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine.
(via B vitamin )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
(via B vitamin )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cobamamide (CHEBI:18408) has role Escherichia coli metabolite (CHEBI:76971)
cobamamide (CHEBI:18408) has role coenzyme (CHEBI:23354)
cobamamide (CHEBI:18408) has role cofactor (CHEBI:23357)
cobamamide (CHEBI:18408) has role human metabolite (CHEBI:77746)
cobamamide (CHEBI:18408) has role prosthetic group (CHEBI:26348)
cobamamide (CHEBI:18408) is a cobalamins (CHEBI:23334)
cobamamide (CHEBI:18408) is a corrinoid (CHEBI:33913)
Incoming adenosylcobalamin 5'-phosphate (CHEBI:49100) has functional parent cobamamide (CHEBI:18408)
IUPAC Name
Coα-[α-(5,6-dimethylbenzimidazolyl)]-Coβ-(5'-deoxy-5'-adenosyl)cobamide
INNs Sources
cobamamida ChemIDplus
cobamamide ChemIDplus
cobamamide WHO MedNet
cobamamidum ChemIDplus
Synonyms Sources
(5,6-Dimethylbenzimidazolyl)cobamide coenzyme KEGG COMPOUND
(5,6-dimethylbenzimidazolyl)cobamide coenzyme MetaCyc
5'-Deoxy-5'-adenosyl vitamin B12 KEGG COMPOUND
5'-Deoxy-5'-adenosyl-5,6-dimethylbenzimidazolylcobamide KEGG COMPOUND
5'-Deoxy-5'-adenosylcobalamin KEGG COMPOUND
5'-deoxyadenosyl vitamin B12 MetaCyc
5'-deoxyadenosyl-5,6-dimethylbenzimidazolylcobamide MetaCyc
5'-deoxyadenosylcobalamin MetaCyc
5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamide KEGG COMPOUND
5,6-Dimethylbenzimidazolyl-Co-5'-deoxy-5'-adenosylcobamide KEGG COMPOUND
adenosylcob(III)alamin UniProt
Adenosylcob(III)alamin KEGG COMPOUND
Adenosylcobalamin KEGG COMPOUND
adenosylcobalamin CBN
AdoCbl CBN
alpha-(5,6-Dimethylbenzimidazolyl)cobamide coenzyme KEGG COMPOUND
Calomide KEGG COMPOUND
Coα-[α-(5,6-dimethylbenzimidazolyl)]-Coβ-adenosylcobamide CBN
Cobalamin coenzyme KEGG COMPOUND
cobamamid MetaCyc
Cobamamide KEGG COMPOUND
cobamide coenzyme MetaCyc
coenzyme B-12 CBN
Coenzyme B12 KEGG COMPOUND
DBC coenzyme ChemIDplus
Deoxyadenosylcobalamin KEGG COMPOUND
Dibencozide KEGG COMPOUND
DMBC coenzyme KEGG COMPOUND
Funacomide KEGG COMPOUND
Vitamin B12 coenzyme KEGG COMPOUND
Brand Name Source
Calomide KEGG DRUG
Manual Xrefs Databases
ADENOSYLCOBALAMIN MetaCyc
B1Z PDBeChem
C00194 KEGG COMPOUND
Cobamamide Wikipedia
DB11191 DrugBank
HMDB0002086 HMDB
View more database links
Registry Numbers Types Sources
13870-90-1 CAS Registry Number KEGG COMPOUND
13870-90-1 CAS Registry Number ChemIDplus
4122932 Reaxys Registry Number Reaxys
439994 Gmelin Registry Number Gmelin
Citations Waiting for Citations Types Sources
11792214 PubMed citation Europe PMC
12093296 PubMed citation Europe PMC
17011224 PubMed citation Europe PMC
Last Modified
06 January 2020