(6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 3901
• Molecular Formular: C16H16ClN3O4
• Molecular Mass: 349.76894
• Monoisotopic Mass: 349.08293369
• SMILES: N[C@@H](C(=O)N[C@@H]1[C@H]2CCC(=C(N2C1=O)C(=O)O)Cl)c1ccccc1
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1[C@H]2CCC(=C(N2C1=O)C(=O)O)Cl
• InChI: InChI=1S/C16H16ClN3O4/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24)/t10-,11-,12-/m1/s1
• InChIKey: JAPHQRWPEGVNBT-IJLUTSLNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: 7-(2-Amino-2-Phenyl-Acetylamino)-3-Chloro-8-Oxo-1-Aza-Bicyclo[4.2.0]Oct-2-Ene-2-Carboxylic Acid

Database IDs

• PubChem SID: 160967336; 46507072
• PubChem CID: 12897341

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.1261737
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.3995888
• LogD (pH = 7.4): -2.6549032
• Log P: -2.3996444
• Molar Refractivity: 86.6375 cm^3
• Polarizability: 33.446136 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.55
• LOG S: -3.03
• Solubility (Water): 3.25e-01 g/l

DETAILS

DrugBank - DB04293

Drug information: experimental