sodium (2S,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-carboxylate

• ChemBase ID: 155978
• Molecular Formular: C19H18N3NaO5S
• Molecular Mass: 423.41809
• Monoisotopic Mass: 423.08648597
• SMILES: Cc1c(c(no1)c1ccccc1)C(=O)N[C@H]1C2N(C1=O)[C@H](C(S2)(C)C)C(=O)[O-].[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1N2C(=O)[C@H](C2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1.[Na+]
• InChI: InChI=1S/C19H19N3O5S.Na/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);/q;+1/p-1/t13-,14+,17?;/m1./s1
• InChIKey: VDUVBBMAXXHEQP-ZTRPPZFVSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,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-carboxylate
• IUPAC Traditional name: sodium (2S,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-carboxylate
• Synonyms: Oxacillin sodium salt; 苯唑西林 钠盐

Database IDs

• CAS Number: 1173-88-2
• EC Number: 214-636-3
• MDL Number: MFCD00082382
• Beilstein Number: 4098179
• PubChem SID: 24857028; 162250116
• PubChem CID: 23681133

CALCULATED PROPERTIES

• Acid pKa: 3.7509665
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.05194399
• LogD (pH = 7.4): -1.5865542
• Log P: 1.697695
• Molar Refractivity: 112.6694 cm^3
• Polarizability: 39.886116 Å^3
• Polar Surface Area: 115.57 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: XH9100000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ~95% (TLC)
• Impurities: ≤10% water
• Empirical Formula (Hill Notation): C19H18N3NaO5S

DETAILS

Sigma Aldrich - 28221

Application
Oxacillin is used to study mechanisms of penicillinase resistance and antimicrobial susceptibility 1. It has been used to study autolysins2
Biochem/physiol Actions
Oxacillin inhibits bacterial cell wall biosynthesis at the level of transpeptidation (PBP) of peptidoglycan. Used to study mechanisms of penicillinase resistance.