sodium (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-5-(13C)methyl(4,5-13C2)-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate

• ChemBase ID: 167177
• Molecular Formular: C19H18Cl2N3NaO6S
• Molecular Mass: 514.29410935
• Monoisotopic Mass: 513.0325253
• SMILES: O.N12[C@H](SC([C@@H]1C(=O)[O-])(C)C)[C@@H](C2=O)N[13C](=O)[13c]1[13c](onc1c1c(cccc1Cl)Cl)[13CH3].[Na+]
• Canonical SMILES: [O-]C(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)N[13C](=O)[13c]1[13c]([13CH3])onc1c1c(Cl)cccc1Cl.O.[Na+]
• InChI: InChI=1S/C19H17Cl2N3O5S.Na.H2O/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24;;/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1/i1+1,7+1,10+1,15+1
• InChIKey: SIGZQNJITOWQEF-VKFSRZSYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-5-(^1^3C)methyl(4,5-^1^3C₂)-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate
• IUPAC Traditional name: sodium (2S,5R,6R)-6-[3-(2,6-dichlorophenyl)-5-(^1^3C)methyl(4,5-^1^3C₂)-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate
• Synonyms: (2S,5R,6R)-6-[[[3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid-13C4 Sodium Salt Hydrate; 3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolyl Penicillin-13C4 Sodium Salt Monohydrate; Dichlorstapenor-13C4 Sodium; Dicloxacillin-13C4 Sodium Hydrate; P 1011-13C4; Sodium Dicloxacillin-13C4 Hydrate; Sodium Dicloxacillin-13C4 Monohydrate; Dicloxacillin-13C4 Sodium Salt Monohydrate

Database IDs

• PubChem SID: 162261310
• PubChem CID: 71316001

CALCULATED PROPERTIES

• Acid pKa: 3.7486086
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.1539227
• LogD (pH = 7.4): -0.3794561
• Log P: 2.9057844
• Molar Refractivity: 122.279 cm^3
• Polarizability: 43.778053 Å^3
• Polar Surface Area: 115.57 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 195-199°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D436652

Labelled Dicloxacillin (D436650). A semi-synthetic antibiotic related to Penicillin. Antibacterial.

REFERENCES

• Chalikian, T., et al.: J. Mol. Biol., 260, 588 (1996)
• Kharakoz, D., et al.: Biochemistry, 36, 10276 (1996)
• Taboada, P., et al.: Langmuir, 16, 3175 (1996)