Oxacillin (CED0002165)

Record Information
Version1.0
Creation Date2016-05-25 18:22:28 UTC
Update Date2026-08-20 02:39:30 UTC
Accession NumberCHEM022166
Identification
Common NameOxacillin
ClassSmall Molecule
Description
Oxacillin is an organic compound with the formula C19H19N3O5S and an average molecular weight of 401.44 g/mol. Oxacillin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. This compound is identified as a binder, inhibitor, or substrate for nine recorded protein targets, including penicillin-binding protein 1A (pbpA), serine-type D-Ala-D-Ala carboxypeptidase (pbp3), penicillin-binding protein 2a (pbp2a), and penicillin-binding protein 2B (penA), among five other proteins. It is found in or released from 18 recorded sources across various categories. Within healthcare, pharmaceuticals, and veterinary products, it is associated with antibiotics and penicillins. It is also found in drinking water and water supply systems. Other sources include food, food processing, and cookware, specifically in food preservation and the processing of fish and meats. Additionally, it is recorded in electrical and electronic equipment, such as video games, television systems, electrodes, hybrid capacitors, and electrically stimulated smoking devices. Household cleaning and consumer products also serve as sources, including soap detergents, perfumes within detergents and soaps, pipe accessories, other smoking requisites, and non-electric simulated smoking devices. Recorded exposure routes for the compound include oral, intravenous, intramuscular, and inhalation.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(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 acidChEBI
(5-Methyl-3-phenyl-4-isoxazolyl)penicillinChEBI
5-Methyl-3-phenyl-4-isoxazolyl-penicillinChEBI
6beta-(5-Methyl-3-phenylisoxazol-4-yl)penicillanic acidChEBI
OxazocillinChEBI
OxacilinaKegg
(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-carboxylateGenerator
6b-(5-Methyl-3-phenylisoxazol-4-yl)penicillanateGenerator
6b-(5-Methyl-3-phenylisoxazol-4-yl)penicillanic acidGenerator
6beta-(5-Methyl-3-phenylisoxazol-4-yl)penicillanateGenerator
6Β-(5-methyl-3-phenylisoxazol-4-yl)penicillanateGenerator
6Β-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acidGenerator
Oxacillin sodiumHMDB
Oxacillin, monosodium salt, anhydrousHMDB
OxazocillineHMDB
Penicillin, methylphenylisoxazolylHMDB
ProstaphlinHMDB
Methylphenylisoxazolyl penicillinHMDB
Oxacillin, sodiumHMDB
Sodium oxacillinHMDB
Oxacillin, monosodium salt, monohydrateHMDB
Sodium, oxacillinHMDB
Chemical FormulaC19H19N3O5S
Average Molecular Mass401.436 g/mol
Monoisotopic Mass401.105 g/mol
CAS Registry Number66-79-5
IUPAC Name(2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Nameoxacillin
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1)C(O)=O
InChI IdentifierInChI=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
InChI KeyUWYHMGVUTGAWSP-JKIFEVAISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Penam
  • Benzenoid
  • Monocyclic benzene moiety
  • Isoxazole
  • Tertiary carboxylic acid amide
  • Azole
  • Thiazolidine
  • Heteroaromatic compound
  • Beta-lactam
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Azetidine
  • Oxacycle
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP2.05ALOGPS
logP1.7ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-0.12ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area112.74 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.83 m³·mol⁻¹ChemAxon
Polarizability39.61 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9756000000-f6bf977e3f72e4a53dafNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00dr-9422200000-f8a5f80c92e02cdcee18Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-79c009ac45201875c809Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1290000000-4d46550a2c9c9f77458aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-8890000000-4a47690fda1171ea9191Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00e9-9530000000-81bb9ec609f6a7e8c6ddNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00e9-9410000000-b5c01a94c4b433924722Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00e9-9200000000-4bfc7a848a77bc668c0aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01b9-9000000000-927fa2d2be3c33adb44cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-3661f69f0fee17d6a499Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-f568ba02b1720f9fd951Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-0980000000-62551643a67b5e9a21f8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-0920000000-69978fc6eeaa10c71f81Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-92b22bc2f96b5f612718Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-1900000000-4dceea173f6174da433dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-3900000000-3ee73f5cb610870dbdb1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ikj-9800000000-fbc9b294222787b35a80Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0k92-9200000000-a405a812cf5f1a2f17e1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-9100000000-451b59b916ee627de317Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-9000000000-21eb1aa369a09320f715Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-8890000000-be778bbb3e94437c3383Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00e9-9530000000-f551b73da96839b2ad75Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1290000000-282a4aa84e02f3e39071Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0090000000-783cf1cfc09e840058beNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-0980000000-1980586b20bea662e02cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-0920000000-2df57f0b63f3bf629932Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-1900000000-0778ddbcfb5653fd277eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-9a2e14bcdd0d49762e3bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ikc-1972400000-1b4711e093e9f42ab804Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03du-1930000000-b12c4b362713b4bb04ccNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0903-3910000000-8b5cc5bea864dcaf596dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0091000000-b65dbdc0c5b20e629677Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0692000000-6c32b8616abd8c887bd9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1910000000-2ad85244337188941840Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0200900000-85e5a936f161b7328675Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0w2i-0940200000-1a859fcd154937dfcb9dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06ri-0900000000-a0b811ac80c6b23835ebNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0130900000-c2eb094f3b2e178c3a36Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9310100000-caba719d9d7d7f291f79Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-9831000000-3c42810817d011b3ac6cNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
6291.0Log mg/kg[3500:11000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
340PenicillinsHealthcare, pharmaceuticals & veterinary productsNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
564Soap DispensersHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.0778492
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)16.8154
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.0778492
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.0778492
Click to view 3D structureNucleoproteinP15682Influenza A virus (strain A/Wilson-Smith/1933 H1N1)Predicted (SEA)6.53933
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)64.3813
Click to view 3D structureShort transient receptor potential channel 4Q9QUQ5Mus musculusPredicted (SEA)131.565
Click to view 3D structureHexokinase HKDC1Q2TB90HumansPredicted (SEA)37.9126
Mucolipin-3 structureClick to view 3D structureMucolipin-3Q8TDD5HumansPredicted (SEA)13.5458
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP00811Escherichia coli (strain K12)Predicted (SEA)6.30579
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)2.72472
Click to view 3D structureIon channel NompCQ7T1G6Danio rerioPredicted (SEA)9.03051
Click to view 3D structureATP-dependent molecular chaperone HSP82C4YTQ8Candida albicans (strain WO-1) (Yeast)Predicted (SEA)625.986
Prostaglandin G/H synthase 2 structureClick to view 3D structureProstaglandin G/H synthase 2P35354HumansPredicted (SEA)944.545
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)5179.78
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)4826.65
Gastrin/cholecystokinin type B receptor structureClick to view 3D structureGastrin/cholecystokinin type B receptorP32239HumansPredicted (SEA)434.321
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)3963.69
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)4839.89
Click to view 3D structureCholecystokinin receptor type AP30551Rattus norvegicusPredicted (SEA)311.008
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)4540.56
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)5815.1
Substance-K receptor structureClick to view 3D structureSubstance-K receptorP21452HumansPredicted (SEA)1085.53
Neuromedin-K receptor structureClick to view 3D structureNeuromedin-K receptorP29371HumansPredicted (SEA)802.081
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)3805.19
Concentrations
Not Available
External Links
DrugBank IDDB00713
HMDB IDHMDB0014851
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOxacillin
Chemspider ID5961
ChEBI ID7809
PubChem Compound ID6196
Kegg Compound IDC07334
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14010809
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20407237
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24295979
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24936596
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=8566082