D-cycloserine (CHEBI:40009)

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ChEBI Name	D-cycloserine

ChEBI ID	CHEBI:40009

ChEBI ASCII Name	D-cycloserine

Definition	A 4-amino-1,2-oxazolidin-3-one that has R configuration. It is an antibiotic produced by Streptomyces garyphalus or S. orchidaceus and is used as part of a multi-drug regimen for the treatment of tuberculosis when resistance to, or toxicity from, primary drugs has developed. An analogue of D-alanine, it interferes with bacterial cell wall synthesis in the cytoplasm by competitive inhibition of L-alanine racemase (which forms D-alanine from L-alanine) and D-alanine—D-alanine ligase (which incorporates D-alanine into the pentapeptide required for peptidoglycan formation and bacterial cell wall synthesis).

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

Secondary ChEBI IDs	CHEBI:4030

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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-/m1/s1

InChIKey

DYDCUQKUCUHJBH-UWTATZPHSA-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):	antimetabolite A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. NMDA receptor agonist An excitatory amino acid agonist which binds to NMDA receptors and triggers a response. antitubercular agent A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis. antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. (via heterocyclic antibiotic )

Application(s):	NMDA receptor agonist An excitatory amino acid agonist which binds to NMDA receptors and triggers a response. antiinfective agent A substance used in the prophylaxis or therapy of infectious diseases. antitubercular agent A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.

ChEBI Ontology
Outgoing	D-cycloserine (CHEBI:40009) has role antiinfective agent (CHEBI:35441) D-cycloserine (CHEBI:40009) has role antimetabolite (CHEBI:35221) D-cycloserine (CHEBI:40009) has role antitubercular agent (CHEBI:33231) D-cycloserine (CHEBI:40009) has role metabolite (CHEBI:25212) D-cycloserine (CHEBI:40009) has role NMDA receptor agonist (CHEBI:64571) D-cycloserine (CHEBI:40009) is a 4-amino-1,2-oxazolidin-3-one (CHEBI:23503) D-cycloserine (CHEBI:40009) is a organonitrogen heterocyclic antibiotic (CHEBI:25558) D-cycloserine (CHEBI:40009) is a organooxygen heterocyclic antibiotic (CHEBI:25807) D-cycloserine (CHEBI:40009) is conjugate base of D-cycloserine(1+) (CHEBI:75929) D-cycloserine (CHEBI:40009) is enantiomer of L-cycloserine (CHEBI:75592) D-cycloserine (CHEBI:40009) is tautomer of D-cycloserine zwitterion (CHEBI:74159)

Incoming	DL-cycloserine (CHEBI:27792) has part D-cycloserine (CHEBI:40009) D-cycloserine(1+) (CHEBI:75929) is conjugate acid of D-cycloserine (CHEBI:40009) L-cycloserine (CHEBI:75592) is enantiomer of D-cycloserine (CHEBI:40009) D-cycloserine zwitterion (CHEBI:74159) is tautomer of D-cycloserine (CHEBI:40009)

IUPAC Name

(4R)-4-aminoisoxazolidin-3-one

Brand Name	Source
Seromycin	ChemIDplus

Last Modified

22 February 2017