(2R)-2-[(R)-carboxy[(2R)-2-carboxy-2-(4-hydroxyphenyl)acetamido]methoxymethyl]-5-methylidene-5,6-dihydro-2H-1,3-oxazine-4-carboxylic acid

• ChemBase ID: 4289
• Molecular Formular: C18H18N2O10
• Molecular Mass: 422.34292
• Monoisotopic Mass: 422.09614479
• SMILES: CO[C@](NC(=O)[C@H](C(=O)O)c1ccc(O)cc1)([C@H]1OCC(=C)C(=N1)C(=O)O)C(=O)O
• Canonical SMILES: CO[C@]([C@H]1OCC(=C)C(=N1)C(=O)O)(C(=O)O)NC(=O)[C@@H](c1ccc(cc1)O)C(=O)O
• InChI: InChI=1S/C18H18N2O10/c1-8-7-30-16(19-12(8)15(25)26)18(29-2,17(27)28)20-13(22)11(14(23)24)9-3-5-10(21)6-4-9/h3-6,11,16,21H,1,7H2,2H3,(H,20,22)(H,23,24)(H,25,26)(H,27,28)/t11-,16-,18-/m1/s1
• InChIKey: ZTOQXKUYWZBJLG-XNAIMREJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(R)-carboxy[(2R)-2-carboxy-2-(4-hydroxyphenyl)acetamido]methoxymethyl]-5-methylidene-5,6-dihydro-2H-1,3-oxazine-4-carboxylic acid
• IUPAC Traditional name: @moxalactam (hydrolyzed)
• Synonyms: MOXALACTAM (HYDROLYZED)

Database IDs

• PubChem SID: 46507244; 160967721
• PubChem CID: 5288864

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.480772
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -5.551821
• LogD (pH = 7.4): -8.78602
• Log P: 1.553651
• Molar Refractivity: 95.7544 cm^3
• Polarizability: 37.31048 Å^3
• Polar Surface Area: 192.05 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 1.18
• LOG S: -3.07
• Solubility (Water): 3.62e-01 g/l

DETAILS

DrugBank - DB04740

Drug information: experimental