(2S)-2-(3-carbamimidamidophenyl)-3-[hydroxy(3-phenylpropyl)phosphoryl]propanoic acid

• ChemBase ID: 4834
• Molecular Formular: C19H24N3O4P
• Molecular Mass: 389.385321
• Monoisotopic Mass: 389.15044289
• SMILES: c1ccccc1CCC[P@](=O)(O)C[C@H](C(=O)O)c1cc(ccc1)NC(=N)N
• Canonical SMILES: NC(=N)Nc1cccc(c1)[C@@H](C(=O)O)C[P@](=O)(CCCc1ccccc1)O
• InChI: InChI=1S/C19H24N3O4P/c20-19(21)22-16-10-4-9-15(12-16)17(18(23)24)13-27(25,26)11-5-8-14-6-2-1-3-7-14/h1-4,6-7,9-10,12,17H,5,8,11,13H2,(H,23,24)(H,25,26)(H4,20,21,22)/t17-/m0/s1
• InChIKey: HFRHWTYCVGKGIE-KRWDZBQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(3-carbamimidamidophenyl)-3-[hydroxy(3-phenylpropyl)phosphoryl]propanoic acid
• IUPAC Traditional name: (2S)-2-(3-carbamimidamidophenyl)-3-[hydroxy(3-phenylpropyl)phosphoryl]propanoic acid
• Synonyms: (2S)-2-(3-{[AMINO(IMINO)METHYL]AMINO}PHENYL)-3-[(S)-HYDROXY(3-PHENYLPROPYL)PHOSPHORYL]PROPANOIC ACID

Database IDs

• PubChem SID: 160968266; 99443653
• PubChem CID: 23653500

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8999628
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 0.7777887
• LogD (pH = 7.4): -1.0260375
• Log P: 1.8340226
• Molar Refractivity: 116.4888 cm^3
• Polarizability: 40.06941 Å^3
• Polar Surface Area: 136.5 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.25
• LOG S: -4.37
• Solubility (Water): 1.66e-02 g/l

DETAILS

DrugBank - DB07182

Drug information: experimental