(2S)-3-{[(1S)-1-amino-3-phenylpropyl](hydroxy)phosphoryl}-2-benzylpropanoic acid

• ChemBase ID: 5095
• Molecular Formular: C19H24NO4P
• Molecular Mass: 361.371921
• Monoisotopic Mass: 361.14429488
• SMILES: O[P@@](=O)([C@@H](CCc1ccccc1)N)C[C@H](C(=O)O)Cc1ccccc1
• Canonical SMILES: OC(=O)[C@@H](C[P@](=O)([C@@H](CCc1ccccc1)N)O)Cc1ccccc1
• InChI: InChI=1S/C19H24NO4P/c20-18(12-11-15-7-3-1-4-8-15)25(23,24)14-17(19(21)22)13-16-9-5-2-6-10-16/h1-10,17-18H,11-14,20H2,(H,21,22)(H,23,24)/t17-,18+/m1/s1
• InChIKey: QELOIXSGJMIHBZ-MSOLQXFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-{[(1S)-1-amino-3-phenylpropyl](hydroxy)phosphoryl}-2-benzylpropanoic acid
• IUPAC Traditional name: (2S)-3-[(1S)-1-amino-3-phenylpropyl(hydroxy)phosphoryl]-2-benzylpropanoic acid
• Synonyms: (2S)-3-[(R)-[(1S)-1-amino-3-phenylpropyl](hydroxy)phosphoryl]-2-benzylpropanoic acid

Database IDs

• PubChem SID: 160968525; 99443919
• PubChem CID: 25138289

CALCULATED PROPERTIES

JChem

• Acid pKa: -0.057131555
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.6127633
• LogD (pH = 7.4): -1.1928954
• Log P: 1.4996285
• Molar Refractivity: 97.6812 cm^3
• Polarizability: 38.570847 Å^3
• Polar Surface Area: 100.62 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.11
• LOG S: -3.71
• Solubility (Water): 7.09e-02 g/l

DETAILS

DrugBank - DB07448

Drug information: experimental