tolbutamide (CHEBI:27999)

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ChEBI Name	tolbutamide

ChEBI ID	CHEBI:27999

Definition	An N-sulfonylurea that consists of 1-butylurea having a tosyl group attached at the 3-position.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:9616, CHEBI:27019

Supplier Information	ChemicalBook:CB61390339, eMolecules:10526940, ZINC000005846414

Download	Molfile XML SDF

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Wikipedia	License
Proline (symbol Pro or P) is an organic acid classed as a proteinogenic amino acid (used in the biosynthesis of proteins), although it does not contain the amino group -NH2 but is rather a secondary amine. The secondary amine nitrogen is in the protonated form (NH2+) under biological conditions, while the carboxyl group is in the deprotonated −COO− form. The "side chain" from the α carbon connects to the nitrogen forming a pyrrolidine loop, classifying it as a aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it from the non-essential amino acid L-glutamate. It is encoded by all the codons starting with CC (CCU, CCC, CCA, and CCG). Proline is the only proteinogenic amino acid which is a secondary amine, as the nitrogen atom is attached both to the α-carbon and to a chain of three carbons that together form a five-membered ring.
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Formula

C12H18N2O3S

Net Charge

Average Mass

270.34800

Monoisotopic Mass

270.10381

InChI

InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)

InChIKey

JLRGJRBPOGGCBT-UHFFFAOYSA-N

SMILES

CCCCNC(=O)NS(=O)(=O)c1ccc(C)cc1

Metabolite of Species	Details
Homo sapiens (NCBI:txid9606)	See: DOI

Roles Classification
Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). insulin secretagogue A secretagogue that causes the secretion of insulin. potassium channel blocker An agent that inhibits cell membrane glycoproteins that are selectively permeable to potassium ions.

Application(s):	hypoglycemic agent A drug which lowers the blood glucose level.

ChEBI Ontology
Outgoing	tolbutamide (CHEBI:27999) has role human metabolite (CHEBI:77746) tolbutamide (CHEBI:27999) has role hypoglycemic agent (CHEBI:35526) tolbutamide (CHEBI:27999) has role insulin secretagogue (CHEBI:90415) tolbutamide (CHEBI:27999) has role potassium channel blocker (CHEBI:50509) tolbutamide (CHEBI:27999) is a N-sulfonylurea (CHEBI:76983)

IUPAC Name

N-[(butylamino)carbonyl]-4-methylbenzenesulfonamide

Synonyms	Sources
1-Butyl-3-(p-methylphenylsulfonyl)urea	ChemIDplus
1-Butyl-3-(p-tolylsulfonyl)urea	ChemIDplus
1-Butyl-3-tosylurea	ChemIDplus
1-p-Toluenesulfonyl-3-butylurea	ChemIDplus
3-(p-Tolyl-4-sulfonyl)-1-butylurea	ChemIDplus
N-(4-Methylbenzenesulfonyl)-N'-butylurea	ChemIDplus
N-(4-Methylphenylsulfonyl)-N'-butylurea	ChemIDplus
N-(p-Methylbenzenesulfonyl)-N'-butylurea	NIST Chemistry WebBook
N-(Sulfonyl-p-methylbenzene)-N'-N-butylurea	NIST Chemistry WebBook
N-Butyl-N'-(4-methylphenylsulfonyl)urea	ChemIDplus
N-Butyl-N'-(p-tolylsulfonyl)urea	ChemIDplus
N-Butyl-N'-p-toluenesulfonylurea	ChemIDplus
N-n-Butyl-N'-tosylurea	ChemIDplus
Orinase (TN)	KEGG DRUG
Tolbutamide	KEGG COMPOUND
Tolylsulfonylbutylurea	NIST Chemistry WebBook

Last Modified

22 February 2017