[(5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate hydrochloride

• ChemBase ID: 176820
• Molecular Formular: C22H30ClN3O6S
• Molecular Mass: 500.0081
• Monoisotopic Mass: 499.15438438
• SMILES: Cl.[C@H]1(C(=O)N2[C@@H]1SC(C2C(=O)OCOC(=O)C(C)(C)C)(C)C)NC(=O)[C@H](N)c1ccccc1
• Canonical SMILES: O=C([C@@H](c1ccccc1)N)N[C@@H]1C(=O)N2[C@@H]1SC(C2C(=O)OCOC(=O)C(C)(C)C)(C)C.Cl
• InChI: InChI=1S/C22H29N3O6S.ClH/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12;/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26);1H/t13-,14-,15?,18-;/m1./s1
• InChIKey: DQECFVGMGBQCPA-SCMHDDPHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate hydrochloride
• IUPAC Traditional name: [(5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate hydrochloride
• Synonyms: (2S,5R,6R)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (2,2-Dimethyl-1-oxopropoxy)methyl Ester Hydrochloride; Alphacilina; Alphacillin; Ampicillin Pivaloxyoxymethyl Ester Hydrochloride; Berocillin; Centurina; Diancina; Inacilin; Maxifen; Pivaloyloxymethyl D-(-)-α-Aminophenylacetamidopenicillanate Hydrochloride; Pivatil; Pondocil; Pondocillin; Pondocillina; Sanguicillin; Pivampicillin Hydrochloride

Database IDs

• CAS Number: 26309-95-5
• PubChem SID: 164232730
• PubChem CID: 71751713

CALCULATED PROPERTIES

• Acid pKa: 11.707929
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.15542963
• LogD (pH = 7.4): 1.7449553
• Log P: 2.0651925
• Molar Refractivity: 116.2483 cm^3
• Polarizability: 46.953476 Å^3
• Polar Surface Area: 128.03 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P551800

Semi-synthetic antibiotic related to Penicillin (P223500). Antibacterial.

REFERENCES

• von Daehne, et al.: J. Med. Chem., 13, 607 (1970)
• Ehrnebo, M., et al.: J. Pharmacokinet. Biopharm., 7, 429 (1970)