CHEBI:40009 - D-cycloserine

ChEBI IDCHEBI:40009
ChEBI NameD-cycloserine
Stars
ASCII NameD-cycloserine
DefinitionA 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).
Secondary ChEBI IDCHEBI:4030
Last Modified22 February 2017
DownloadsMolfile
FormulaC3H6N2O2
Net Charge0
Average Mass102.093
Monoisotopic Mass102.04293
SMILES[H][C@@]1(N)CONC1=O
InChIInChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
InChIKeyDYDCUQKUCUHJBH-UWTATZPHSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
NMDA receptor agonist  An excitatory amino acid agonist which binds to NMDA receptors and triggers a response.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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
INNs  Source
cicloserinaChemIDplus
cycloserinumChemIDplus
cycloserineChemIDplus
cyclosérineWHO MedNet
Synonyms  Source
(R)-4-AMINO-ISOXAZOLIDIN-3-ONEPDBeChem
(+)-4-amino-3-isoxazolidinoneChemIDplus
D-CycloserineChemIDplus
α-CycloserineNIST Chemistry WebBook
DCSChemIDplus
D-4-amino-3-isoxazolidoneChemIDplus
Brand Name  Source
SeromycinChemIDplus
Manual XrefsDatabases
4AXPDBeChem
LMPK14000007LIPID MAPS
CycloserineWikipedia
DB00260DrugBank
US2772280Patent
US2840565Patent
HMDB0014405HMDB
CPD-2482MetaCyc
D00877KEGG DRUG
LSM-5932LINCS
759DrugCentral
Registry NumbersSources
Reaxys:80798Reaxys
CAS:68-41-7ChemIDplus
CAS:68-41-7NIST Chemistry WebBook
Citations