L-cycloserine (CHEBI:75592)

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ChEBI Name	L-cycloserine

ChEBI ID	CHEBI:75592

ChEBI ASCII Name	L-cycloserine

Definition	A 4-amino-1,2-oxazolidin-3-one that has S configuration. An antibiotic isolated from Erwinia uredovora.

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

Supplier Information

Download	Molfile XML SDF

Formula

C3H6N2O2

Net Charge

Average Mass

102.09190

Monoisotopic Mass

102.04293

InChI

InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m0/s1

InChIKey

DYDCUQKUCUHJBH-REOHCLBHSA-N

SMILES

[H][C@]1(N)CONC1=O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor An EC 2.3.1.* (acyltransferase transferring other than amino-acyl group) inhibitor that interferes with the action of serine palmitoyltransferase (EC 2.3.1.50). anti-HIV agent An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.

Application(s):	anticonvulsant A drug used to prevent seizures or reduce their severity.

ChEBI Ontology
Outgoing	L-cycloserine (CHEBI:75592) has role anti-HIV agent (CHEBI:64946) L-cycloserine (CHEBI:75592) has role anticonvulsant (CHEBI:35623) L-cycloserine (CHEBI:75592) has role EC 2.3.1.50 (serine C-palmitoyltransferase) inhibitor (CHEBI:59647) L-cycloserine (CHEBI:75592) is a 4-amino-1,2-oxazolidin-3-one (CHEBI:23503) L-cycloserine (CHEBI:75592) is enantiomer of D-cycloserine (CHEBI:40009)

Incoming	DL-cycloserine (CHEBI:27792) has part L-cycloserine (CHEBI:75592) D-cycloserine (CHEBI:40009) is enantiomer of L-cycloserine (CHEBI:75592)

IUPAC Name

(4S)-4-amino-1,2-oxazolidin-3-one

Last Modified

25 February 2016