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 244.08816
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:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Homo sapiens (NCBI:txid9606) Found in saliva (UBERON:0001836). See: Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Homo sapiens (NCBI:txid9606) Found in cerebrospinal fluid (UBERON:0001359). See: PubMed
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606) Found in urine (BTO:0001419). See: Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606) From MetaboLights See: MetaboLights Study
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).
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).
fundamental metabolite
Any metabolite produced by all living cells.
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.
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 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 coenzyme (CHEBI:23354)
biotin (CHEBI:15956) has role cofactor (CHEBI:23357)
biotin (CHEBI:15956) has role fundamental metabolite (CHEBI:78675)
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 a vitamin B7 (CHEBI:176841)
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
biotin WHO MedNet
biotina WHO MedNet
biotine WHO MedNet
biotinum WHO MedNet
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 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
Manual Xrefs Databases
149962 ChemSpider
373 DrugCentral
Biotin Wikipedia
BIOTIN MetaCyc
BTN PDBeChem
C00000756 KNApSAcK
C00120 KEGG COMPOUND
D00029 KEGG DRUG
DB00121 DrugBank
FDB014510 FooDB
HMDB0000030 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 ChemIDplus
58-85-5 CAS Registry Number NIST Chemistry WebBook
86838 Beilstein Registry Number Beilstein
86838 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 July 2021