4-[(2R,3R)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoic acid

• ChemBase ID: 5208
• Molecular Formular: C15H16Cl2N2O8
• Molecular Mass: 423.20214
• Monoisotopic Mass: 422.02837084
• SMILES: C(Cl)(Cl)C(=O)N[C@H](COC(=O)CCC(=O)O)[C@H](O)c1ccc([N+](=O)[O-])cc1
• Canonical SMILES: OC(=O)CCC(=O)OC[C@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
• InChI: InChI=1S/C15H16Cl2N2O8/c16-14(17)15(24)18-10(7-27-12(22)6-5-11(20)21)13(23)8-1-3-9(4-2-8)19(25)26/h1-4,10,13-14,23H,5-7H2,(H,18,24)(H,20,21)/t10-,13-/m1/s1
• InChIKey: LIRCDOVJWUGTMW-ZWNOBZJWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2R,3R)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoic acid
• IUPAC Traditional name: 4-[(2R,3R)-2-(2,2-dichloroacetamido)-3-hydroxy-3-(4-nitrophenyl)propoxy]-4-oxobutanoic acid
• Synonyms: CHLORAMPHENICOL SUCCINATE

Database IDs

• PubChem SID: 160968638; 99444036
• PubChem CID: 656580

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6750705
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -0.6805518
• LogD (pH = 7.4): -2.3224185
• Log P: 1.1446916
• Molar Refractivity: 93.2455 cm^3
• Polarizability: 36.007523 Å^3
• Polar Surface Area: 158.75 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.34
• LOG S: -3.58
• Solubility (Water): 1.12e-01 g/l

DETAILS

DrugBank - DB07565

Drug information: experimental