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CHEBI:18408 - cobamamide

ChEBI IDCHEBI:18408
ChEBI Namecobamamide
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:3797, CHEBI:13739, CHEBI:23340
Last Modified6 January 2020
DownloadsMolfile
FormulaC72H100CoN18O17P
Net Charge0
Average Mass1579.608
Monoisotopic Mass1578.65834
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](O)[C@H](O[C@@H]4CO)n4c[n+](c5cc(C)c(C)cc54)[Co-3]456([CH2][C@H]7O[C@@H](n8cnc9c(N)ncnc98)[C@H](O)[C@@H]7O)[N]1C3=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
InChIInChI=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
InChIKeyZIHHMGTYZOSFRC-OUCXYWSSSA-L
Wikipedia
Species of MetaboliteComponentSourceComments
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Roles Classification
Biological Roles:
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
coenzyme  A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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).
prosthetic group  A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
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).
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.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
cobamamidaChemIDplus
cobamamideWHO MedNet
cobamamideChemIDplus
cobamamidumChemIDplus
Synonyms  Source
5,6-Dimethylbenzimidazolyl-5-deoxyadenosyl-cobamideKEGG COMPOUND
5,6-Dimethylbenzimidazolyl-Co-5'-deoxy-5'-adenosylcobamideKEGG COMPOUND
(5,6-dimethylbenzimidazolyl)cobamide coenzymeMetaCyc
(5,6-Dimethylbenzimidazolyl)cobamide coenzymeKEGG COMPOUND
5'-Deoxy-5'-adenosyl-5,6-dimethylbenzimidazolylcobamideKEGG COMPOUND
5'-Deoxy-5'-adenosylcobalaminKEGG COMPOUND
Brand Name  Source
CalomideKEGG DRUG
UniProt Name  Source
adenosylcob(III)alaminUniProt
Manual XrefsDatabases
ADENOSYLCOBALAMINMetaCyc
B1ZPDBeChem
C00194KEGG COMPOUND
CobamamideWikipedia
DB11191DrugBank
HMDB0002086HMDB
Registry NumbersSources
Reaxys:4122932Reaxys
Gmelin:439994Gmelin
CAS:13870-90-1KEGG COMPOUND
CAS:13870-90-1ChemIDplus
Citations