(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[2-(2H5)phenoxyacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 176264
• Molecular Formular: C16H18N2O5S
• Molecular Mass: 350.38952
• Monoisotopic Mass: 350.09364269
• SMILES: [C@H]1(C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)NC(=O)COc1ccccc1
• Canonical SMILES: O=C(N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)COc1ccccc1
• InChI: InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
• InChIKey: BPLBGHOLXOTWMN-MBNYWOFBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[2-(^2H₅)phenoxyacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[2-(^2H₅)phenoxyacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Synonyms: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(2-phenoxy-d5-acetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid; 6-(Phenoxy-d5-acetamido)penicillanic Acid; Phenoxymethylpenicillin-d5; Phenospen-d5; Oracilline-d5; V-Cillin-d5; Penicillin V-d5

Database IDs

• PubChem SID: 164232174
• PubChem CID: 45040190

CALCULATED PROPERTIES

• Acid pKa: 3.390268
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.3336357
• LogD (pH = 7.4): -2.6421306
• Log P: 0.7632417
• Molar Refractivity: 85.768 cm^3
• Polarizability: 34.092434 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 118-121°C (dec)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - P223502

Antibacterial.

REFERENCES

• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)
• Dunham, J.M., et al.: Anal. Profiles Drug Subs., 1, 249 (1971)