biotin (CHEBI:15956)

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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

Supplier Information	ChemicalBook:CB6441658, eMolecules:530918

Download	Molfile XML SDF

more structures >>

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32 33 0 0 0 0 999 V2000

1.3784 -7.1456 0.2533 C 0 0 0 0 0 0 0 0 0 0 0 0

4.7644 -3.6708 2.6866 C 0 0 2 0 0 0 0 0 0 0 0 0

7.2198 -2.0042 1.0779 C 0 0 0 0 0 0 0 0 0 0 0 0

5.8747 -2.6222 2.8463 C 0 0 2 0 0 0 0 0 0 0 0 0

5.3852 -1.2557 2.2608 C 0 0 2 0 0 0 0 0 0 0 0 0

3.9691 -1.4214 1.6815 C 0 0 0 0 0 0 0 0 0 0 0 0

5.3610 -5.0709 2.5126 C 0 0 0 0 0 0 0 0 0 0 0 0

4.2658 -6.1437 2.5628 C 0 0 0 0 0 0 0 0 0 0 0 0

3.3183 -6.0367 1.3634 C 0 0 0 0 0 0 0 0 0 0 0 0

2.2874 -7.1640 1.4606 C 0 0 0 0 0 0 0 0 0 0 0 0

6.3260 -0.9667 1.1650 N 0 0 0 0 0 0 0 0 0 0 0 0

7.0218 -2.9976 2.0026 N 0 0 0 0 0 0 0 0 0 0 0 0

0.4307 -6.1781 0.1302 O 0 0 0 0 0 0 0 0 0 0 0 0

1.4991 -7.9852 -0.6095 O 0 0 0 0 0 0 0 0 0 0 0 0

8.1065 -2.0392 0.2558 O 0 0 0 0 0 0 0 0 0 0 0 0

3.8454 -3.1615 1.2215 S 0 0 0 0 0 0 0 0 0 0 0 0

4.2444 -3.7748 3.6629 H 0 0 0 0 0 0 0 0 0 0 0 0

6.1791 -2.5837 3.9141 H 0 0 0 0 0 0 0 0 0 0 0 0

5.3754 -0.4203 2.9932 H 0 0 0 0 0 0 0 0 0 0 0 0

3.8786 -0.7302 0.8163 H 0 0 0 0 0 0 0 0 0 0 0 0

3.2473 -1.1230 2.4716 H 0 0 0 0 0 0 0 0 0 0 0 0

6.0917 -5.2580 3.3284 H 0 0 0 0 0 0 0 0 0 0 0 0

5.8791 -5.1252 1.5312 H 0 0 0 0 0 0 0 0 0 0 0 0

3.6793 -6.0174 3.4979 H 0 0 0 0 0 0 0 0 0 0 0 0

4.7427 -7.1471 2.5569 H 0 0 0 0 0 0 0 0 0 0 0 0

3.8949 -6.1366 0.4191 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8011 -5.0536 1.3799 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8105 -8.1432 1.5049 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6745 -7.0292 2.3773 H 0 0 0 0 0 0 0 0 0 0 0 0

6.3557 -0.1281 0.5273 H 0 0 0 0 0 0 0 0 0 0 0 0

7.6217 -3.8626 2.0537 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3340 -5.4703 0.8471 H 0 0 0 0 0 0 0 0 0 0 0 0

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4 12 1 0 0 0 0

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3 15 2 0 0 0 0

3 12 1 0 0 0 0

3 11 1 0 0 0 0

2 16 1 0 0 0 0

2 7 1 0 0 0 0

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1 14 2 0 0 0 0

1 13 1 0 0 0 0

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Wikipedia	License
Theophylline, also known as 1,3-dimethylxanthine, is a drug that inhibits phosphodiesterase and blocks adenosine receptors. It is used to treat chronic obstructive pulmonary disease (COPD) and asthma. Its pharmacology is similar to other methylxanthine drugs (e.g., theobromine and caffeine). Trace amounts of theophylline are naturally present in tea, coffee, chocolate, yerba maté, guarana, and kola nut. The name 'theophylline' derives from "Thea"—the former genus name for tea + Legacy Greek φύλλον (phúllon, "leaf") + -ine.
Read full article at Wikipedia

Formula

C10H16N2O3S

Net Charge

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	Reaxys Registry Number	Reaxys

Citations

Last Modified

22 July 2021

CHEBI:15956 - biotin

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