CHEBI:40009 - D-cycloserine

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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 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-/m1/s1
InChIKey DYDCUQKUCUHJBH-UWTATZPHSA-N
SMILES [H][C@@]1(N)CONC1=O
Roles Classification
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.
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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
INNs Sources
cicloserina ChemIDplus
cycloserine ChemIDplus
cyclosérine WHO MedNet
cycloserinum ChemIDplus
Synonyms Sources
(+)-4-amino-3-isoxazolidinone ChemIDplus
(+)-cycloserine ChEBI
(R)-4-AMINO-ISOXAZOLIDIN-3-ONE PDBeChem
α-Cycloserine NIST Chemistry WebBook
cyclo-D-serine ChemIDplus
D-(+)-cycloserine ChEBI
D-4-amino-3-isoxazolidinone ChemIDplus
D-4-amino-3-isoxazolidone ChemIDplus
D-Cycloserine ChemIDplus
D-Cycloserine KEGG COMPOUND
DCS ChemIDplus
orientomycin ChemIDplus
PA 94 ChemIDplus
PA-94 ChemIDplus
Ro-1-9213 ChemIDplus
Brand Name Source
Seromycin ChemIDplus
Database Links Databases
4AX PDBeChem
759 DrugCentral
CPD-2482 MetaCyc
Cycloserine Wikipedia
D00877 KEGG DRUG
DB00260 DrugBank
HMDB0014405 HMDB
LMPK14000007 LIPID MAPS
LSM-5932 LINCS
US2772280 Patent
US2840565 Patent
View more database links
Registry Numbers Types Sources
68-41-7 CAS Registry Number NIST Chemistry WebBook
68-41-7 CAS Registry Number ChemIDplus
80798 Beilstein Registry Number Beilstein
80798 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017