(2S)-2-[(2S)-3-{[(1R)-1-aminoethyl](hydroxy)phosphoryl}-2-benzylpropanamido]-3-phenylpropanoic acid

• ChemBase ID: 6117
• Molecular Formular: C21H27N2O5P
• Molecular Mass: 418.423241
• Monoisotopic Mass: 418.1657586
• SMILES: O=[P@](O)([C@@H](N)C)C[C@@H](Cc1ccccc1)C(=O)N[C@H](C(=O)O)Cc1ccccc1
• Canonical SMILES: O=C([C@@H](C[P@](=O)([C@@H](N)C)O)Cc1ccccc1)N[C@H](C(=O)O)Cc1ccccc1
• InChI: InChI=1S/C21H27N2O5P/c1-15(22)29(27,28)14-18(12-16-8-4-2-5-9-16)20(24)23-19(21(25)26)13-17-10-6-3-7-11-17/h2-11,15,18-19H,12-14,22H2,1H3,(H,23,24)(H,25,26)(H,27,28)/t15-,18-,19+/m1/s1
• InChIKey: MMWNOZXGYRPSCJ-LZQZEXGQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-3-{[(1R)-1-aminoethyl](hydroxy)phosphoryl}-2-benzylpropanamido]-3-phenylpropanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-3-[(1R)-1-aminoethyl(hydroxy)phosphoryl]-2-benzylpropanamido]-3-phenylpropanoic acid
• Synonyms: N-{(2S)-3-[(1R)-1-aminoethyl](hydroxy)phosphoryl-2-benzylpropanoyl}-L-phenylalanine

Database IDs

• PubChem SID: 160969542; 99444977
• PubChem CID: 10601417

CALCULATED PROPERTIES

JChem

• Acid pKa: -0.03695814
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.8654454
• LogD (pH = 7.4): -2.6447725
• Log P: 0.46244788
• Molar Refractivity: 110.4328 cm^3
• Polarizability: 43.487137 Å^3
• Polar Surface Area: 129.72 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.13
• LOG S: -4.06
• Solubility (Water): 3.62e-02 g/l

DETAILS

DrugBank - DB08506

Drug information: experimental