(6R,7R)-7-[(2S)-2-carboxy-2-(4-hydroxyphenyl)acetamido]-7-methoxy-3-methyl-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 2316
• Molecular Formular: C18H18N2O9
• Molecular Mass: 406.34352
• Monoisotopic Mass: 406.10123017
• SMILES: C1(=O)[C@](OC)([C@@H]2N1C(=C(CO2)C)C(=O)O)NC(=O)[C@@H](C(=O)O)c1ccc(cc1)O
• Canonical SMILES: CO[C@@]1(NC(=O)[C@H](c2ccc(cc2)O)C(=O)O)C(=O)N2[C@@H]1OCC(=C2C(=O)O)C
• InChI: InChI=1S/C18H18N2O9/c1-8-7-29-17-18(28-2,16(27)20(17)12(8)15(25)26)19-13(22)11(14(23)24)9-3-5-10(21)6-4-9/h3-6,11,17,21H,7H2,1-2H3,(H,19,22)(H,23,24)(H,25,26)/t11-,17+,18-/m0/s1
• InChIKey: GYYVEEGHXUADBF-PDSMFRHLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-[(2S)-2-carboxy-2-(4-hydroxyphenyl)acetamido]-7-methoxy-3-methyl-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: (6R,7R)-7-[(2S)-2-carboxy-2-(4-hydroxyphenyl)acetamido]-7-methoxy-3-methyl-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• Synonyms: Moxalactam Derivative

Database IDs

• PubChem SID: 46506599; 160965768
• PubChem CID: 17754085

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.018264
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.8108554
• LogD (pH = 7.4): -6.4108644
• Log P: 0.37256926
• Molar Refractivity: 94.3747 cm^3
• Polarizability: 36.484894 Å^3
• Polar Surface Area: 162.7 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.81
• LOG S: -2.28
• Solubility (Water): 2.13e+00 g/l

DETAILS

DrugBank - DB02588

Drug information: experimental