CHEBI:7809 - oxacillin

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ChEBI Name oxacillin
ChEBI ID CHEBI:7809
Definition A penicillin antibiotic carrying a 5-methyl-3-phenylisoxazole-4-carboxamide group at position 6β.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C19H19N3O5S
Net Charge 0
Average Mass 401.43600
Monoisotopic Mass 401.105
InChI InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1
InChIKey UWYHMGVUTGAWSP-JKIFEVAISA-N
SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)c1c(C)onc1-c1ccccc1)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
antibacterial agent
A substance that kills or slows the growth of bacteria.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via heterocyclic antibiotic )
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing oxacillin (CHEBI:7809) has role antibacterial agent (CHEBI:33282)
oxacillin (CHEBI:7809) has role antibacterial drug (CHEBI:36047)
oxacillin (CHEBI:7809) is a penicillin (CHEBI:17334)
oxacillin (CHEBI:7809) is conjugate acid of oxacillin(1−) (CHEBI:52132)
Incoming cloxacillin (CHEBI:49566) has functional parent oxacillin (CHEBI:7809)
oxacillin(1−) (CHEBI:52132) is conjugate base of oxacillin (CHEBI:7809)
IUPAC Name
2,2-dimethyl-6β-(5-methyl-3-phenyl-1,2-oxazole-4-carboxamido)penam-3α-carboxylic acid
Synonyms Sources
(2S,5R,6R)-3,3-dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid IUPAC
(5-methyl-3-phenyl-4-isoxazolyl)penicillin ChemIDplus
5-methyl-3-phenyl-4-isoxazolyl-penicillin ChemIDplus
6β-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acid ChEBI
Oxacillin KEGG COMPOUND
oxazocillin ChemIDplus
Manual Xrefs Databases
2006 DrugCentral
C07334 KEGG COMPOUND
D08307 KEGG DRUG
DB00713 DrugBank
HMDB0014851 HMDB
LSM-6005 LINCS
Oxacillin Wikipedia
US2996501 Patent
View more database links
Registry Numbers Types Sources
1093589 Beilstein Registry Number Beilstein
1093589 Reaxys Registry Number Reaxys
66-79-5 CAS Registry Number KEGG COMPOUND
66-79-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
14010809 PubMed citation Europe PMC
20407237 PubMed citation Europe PMC
24295979 PubMed citation Europe PMC
24936596 PubMed citation Europe PMC
29017833 PubMed citation Europe PMC
8566082 PubMed citation Europe PMC
Last Modified
15 March 2018