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

• ChemBase ID: 162746
• Molecular Formular: C16H18BrN3O4S
• Molecular Mass: 428.30082
• Monoisotopic Mass: 427.02013907
• SMILES: c1(ccc(cc1)[C@H](C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C)N)Br
• Canonical SMILES: N[C@H](c1ccc(cc1)Br)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
• InChI: InChI=1S/C16H18BrN3O4S/c1-16(2)11(15(23)24)20-13(22)10(14(20)25-16)19-12(21)9(18)7-3-5-8(17)6-4-7/h3-6,9-11,14H,18H2,1-2H3,(H,19,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
• InChIKey: YHGWQHFZQZNZCJ-NJBDSQKTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-[(2R)-2-amino-2-(4-bromophenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: (2S,5R,6R)-6-[(2R)-2-amino-2-(4-bromophenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Synonyms: (2S,5R,6R)-6-[[(2R)-2-Amino-2-(4-bromophenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid; 4'-Bromo Ampicillin

Database IDs

• CAS Number: 1356019-52-7
• PubChem SID: 162256881
• PubChem CID: 71314212

CALCULATED PROPERTIES

• Acid pKa: 3.2166853
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.2370328
• LogD (pH = 7.4): -1.5104793
• Log P: -1.2375087
• Molar Refractivity: 95.1463 cm^3
• Polarizability: 37.77193 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B679625

Antibacterial penicillin derivative.