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CHEBI:15956 - biotin

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ChEBI Name biotin
ChEBI ID CHEBI:15956
Definition An organic heterobicyclic compound that consists of 2-oxohexahydro-1H-thieno[3,4-d]imidazole having a valeric acid substituent attached to the tetrahydrothiophene ring. The parent of the class of biotins.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41236, CHEBI:13905, CHEBI:22882, CHEBI:22884, CHEBI:3108
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Formula C10H16N2O3S
Net Charge 0
Average Mass 244.31172
Monoisotopic Mass 244.088
InChI InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
InChIKey YBJHBAHKTGYVGT-ZKWXMUAHSA-N
SMILES [H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:562) See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): prosthetic group
A tightly bound, specific nonpolypeptide unit in a protein determining and involved in its biological activity.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
B vitamin
Any of the group of eight water-soluble vitamins originally thought to be a single compound (vitamin B) that play important roles in cell metabolism. The group comprises vitamin B1, B2, B3, B5, B6, B7, B9, and B12. (Around 20 other compounds were once thought to be B vitamins but are no longer classified as such.)
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).
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
Application(s): B vitamin
Any of the group of eight water-soluble vitamins originally thought to be a single compound (vitamin B) that play important roles in cell metabolism. The group comprises vitamin B1, B2, B3, B5, B6, B7, B9, and B12. (Around 20 other compounds were once thought to be B vitamins but are no longer classified as such.)
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing biotin (CHEBI:15956) has role Escherichia coli metabolite (CHEBI:76971)
biotin (CHEBI:15956) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
biotin (CHEBI:15956) has role B vitamin (CHEBI:75769)
biotin (CHEBI:15956) has role coenzyme (CHEBI:23354)
biotin (CHEBI:15956) has role human metabolite (CHEBI:77746)
biotin (CHEBI:15956) has role mouse metabolite (CHEBI:75771)
biotin (CHEBI:15956) has role nutraceutical (CHEBI:50733)
biotin (CHEBI:15956) has role prosthetic group (CHEBI:26348)
biotin (CHEBI:15956) is a biotins (CHEBI:51570)
biotin (CHEBI:15956) is conjugate acid of biotinate (CHEBI:57586)
Incoming biocytin (CHEBI:27870) has functional parent biotin (CHEBI:15956)
biotin amide (CHEBI:16615) has functional parent biotin (CHEBI:15956)
biotinyl-5'-AMP (CHEBI:3110) has functional parent biotin (CHEBI:15956)
biotinyl-CoA (CHEBI:15516) has functional parent biotin (CHEBI:15956)
GCB (CHEBI:74858) has functional parent biotin (CHEBI:15956)
vitamin B complex (CHEBI:75782) has part biotin (CHEBI:15956)
biotinate (CHEBI:57586) is conjugate base of biotin (CHEBI:15956)
biotinyl group (CHEBI:22885) is substituent group from biotin (CHEBI:15956)
IUPAC Name
5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
INNs Sources
biotina ChemIDplus
biotine ChemIDplus
biotinum ChemIDplus
Synonyms Sources
(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acid HMDB
(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-valeric acid HMDB
5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid HMDB
Biotin KEGG COMPOUND
BIOTIN PDBeChem
cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid HMDB
cis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acid HMDB
cis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid HMDB
Coenzyme R KEGG COMPOUND
D-(+)-biotin NIST Chemistry WebBook
D-Biotin KEGG COMPOUND
vitamin B7 NIST Chemistry WebBook
Vitamin H KEGG COMPOUND
Database Links Databases
Biotin Wikipedia
BIOTIN MetaCyc
BTN PDBeChem
C00000756 KNApSAcK
C00120 KEGG COMPOUND
D00029 KEGG DRUG
DB00121 DrugBank
HMDB00030 HMDB
LSM-3994 LINCS
MOL000144 COMe
View more database links
Registry Numbers Types Sources
1918703 Gmelin Registry Number Gmelin
58-85-5 CAS Registry Number KEGG COMPOUND
58-85-5 CAS Registry Number NIST Chemistry WebBook
58-85-5 CAS Registry Number ChemIDplus
86838 Reaxys Registry Number Reaxys
86838 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11435506 PubMed citation Europe PMC
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Last Modified
07 March 2016