(2S)-2-{4-[hydroxy(4-nitrophenoxy)phosphoryl]butanamido}propanoic acid

• ChemBase ID: 5994
• Molecular Formular: C13H17N2O8P
• Molecular Mass: 360.256441
• Monoisotopic Mass: 360.07225214
• SMILES: [P@@](=O)(Oc1ccc(cc1)[N+](=O)[O-])(O)CCCC(=O)N[C@@H](C)C(=O)O
• Canonical SMILES: O=C(N[C@H](C(=O)O)C)CCC[P@](=O)(Oc1ccc(cc1)[N+](=O)[O-])O
• InChI: InChI=1S/C13H17N2O8P/c1-9(13(17)18)14-12(16)3-2-8-24(21,22)23-11-6-4-10(5-7-11)15(19)20/h4-7,9H,2-3,8H2,1H3,(H,14,16)(H,17,18)(H,21,22)/t9-/m0/s1
• InChIKey: KBXXIYHMPQZHCH-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{4-[hydroxy(4-nitrophenoxy)phosphoryl]butanamido}propanoic acid
• IUPAC Traditional name: (2S)-2-{4-[hydroxy(4-nitrophenoxy)phosphoryl]butanamido}propanoic acid
• Synonyms: PARA-NITROPHENYL PHOSPHONOBUTANOYL L-ALANINE; PARA-NITROPHENYL PHOSPHONOBUTANOYL D-ALANINE

Database IDs

• PubChem SID: 160969419; 99444882; 99444848
• PubChem CID: 5496653

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8105723
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -3.616744
• LogD (pH = 7.4): -5.1824975
• Log P: 0.4583791
• Molar Refractivity: 81.7228 cm^3
• Polarizability: 31.554617 Å^3
• Polar Surface Area: 158.75 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.44
• LOG S: -3.52
• Solubility (Water): 1.08e-01 g/l

DETAILS

DrugBank - DB08377

Drug information: experimental

DrugBank - DB08411

Drug information: experimental