loading...| Preferred Name |
D-cycloserine |
|
| Synonyms |
(4R)-4-aminoisoxazolidin-3-one D-Cycloserine D-4-amino-3-isoxazolidinone cyclo-D-serine orientomycin cicloserina cycloserine alpha-Cycloserine D-4-amino-3-isoxazolidone D-(+)-cycloserine (+)-cycloserine (R)-4-AMINO-ISOXAZOLIDIN-3-ONE cycloserinum (+)-4-amino-3-isoxazolidinone DCS PA 94 PA-94 Ro-1-9213 Seromycin |
|
| Definitions |
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). |
|
| ID |
http://purl.obolibrary.org/obo/CHEBI_40009 |
|
| charge |
0 |
|
| database_cross_reference |
Reaxys:80798 PMID:23438729 PMID:18316423 PMID:22632472 PMID:22892161 Wikipedia:Cycloserine HMDB:HMDB0014405 LINCS:LSM-5932 Beilstein:80798 PMID:18486041 Drug_Central:759 PMID:18930757 CAS:68-41-7 PMID:23542909 Patent:US2840565 LIPID_MAPS_instance:LMPK14000007 PMID:22234379 PMID:4555420 PMID:23523746 PMID:23416058 KEGG:D00877 PMID:23685206 PMID:22368237 MetaCyc:CPD-2482 PMID:23174090 PDBeChem:4AX PMID:23656850 PMID:5006234 PMID:17707326 PMID:12076471 DrugBank:DB00260 Patent:US2772280 |
|
| 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). |
|
| formula |
C3H6N2O2 |
|
| has role |
http://purl.obolibrary.org/obo/CHEBI_33231 http://purl.obolibrary.org/obo/CHEBI_35221 |
|
| has_alternative_id |
CHEBI:4030 |
|
| has_exact_synonym |
(4R)-4-aminoisoxazolidin-3-one D-Cycloserine |
|
| has_obo_namespace |
chebi_ontology |
|
| has_related_synonym |
D-4-amino-3-isoxazolidinone cyclo-D-serine orientomycin cicloserina cycloserine alpha-Cycloserine D-4-amino-3-isoxazolidone D-(+)-cycloserine (+)-cycloserine (R)-4-AMINO-ISOXAZOLIDIN-3-ONE cycloserinum (+)-4-amino-3-isoxazolidinone DCS PA 94 PA-94 Ro-1-9213 Seromycin |
|
| has_RxCUI |
3007 |
|
| id |
CHEBI:40009 |
|
| in_subset | ||
| 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 |
|
| is conjugate base of | ||
| is enantiomer of | ||
| is tautomer of | ||
| label |
D-cycloserine Cycloserine |
|
| mass |
102.09190 |
|
| monoisotopicmass |
102.04293 |
|
| notation |
CHEBI:40009 |
|
| prefLabel |
D-cycloserine |
|
| smiles |
[H][C@@]1(N)CONC1=O |
|
| subClassOf |
http://purl.obolibrary.org/obo/CHEBI_25807 |