CHEBI:75592 - L-cycloserine

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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
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Formula C3H6N2O2
Net Charge 0
Average Mass 102.09190
Monoisotopic Mass 102.043
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.
View more via ChEBI Ontology
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
INNs Sources
levcicloserina ChemIDplus
levcyclosérine WHO MedNet
levcycloserine ChemIDplus
levcycloserinum ChemIDplus
Synonyms Sources
(−)-4-amino-3-isoxazolidinone ChemIDplus
(−)-4-aminoisoxazolidin-3-one ChEBI
(−)-cycloserine ChEBI
(4S)-4-aminoisoxazolidin-3-one IUPAC
(S)-(−)-cycloserine ChemIDplus
(S)-4-amino-3-isoxazolidinone ChemIDplus
(S)-4-amino-isoxazolidin-3-one ChEBI
cyclo-L-serine ChemIDplus
L-4-aminoisoxazolidin-3-one ChEBI
L-CS ChEBI
Manual Xrefs Databases
CPD-2483 MetaCyc
D04706 KEGG DRUG
DB00260 DrugBank
HMDB0014405 HMDB
LSM-5639 LINCS
View more database links
Registry Numbers Types Sources
339-72-0 CAS Registry Number ChemIDplus
80799 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19932170 PubMed citation Europe PMC
3430071 PubMed citation Europe PMC
3771514 PubMed citation Europe PMC
4150977 PubMed citation Europe PMC
638858 PubMed citation Europe PMC
6501090 PubMed citation Europe PMC
6723595 PubMed citation Europe PMC
7353584 PubMed citation Europe PMC
8556395 PubMed citation Europe PMC
Last Modified
25 February 2016