(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]-N-[(4-carbamimidoylphenyl)methyl]pyrrolidine-2-carboxamide

• ChemBase ID: 4658
• Molecular Formular: C22H27N5O2
• Molecular Mass: 393.48208
• Monoisotopic Mass: 393.21647513
• SMILES: N1([C@H](C(=O)NCc2ccc(C(=N)N)cc2)CCC1)C(=O)[C@H](N)Cc1ccccc1
• Canonical SMILES: O=C([C@@H]1CCCN1C(=O)[C@@H](Cc1ccccc1)N)NCc1ccc(cc1)C(=N)N
• InChI: InChI=1S/C22H27N5O2/c23-18(13-15-5-2-1-3-6-15)22(29)27-12-4-7-19(27)21(28)26-14-16-8-10-17(11-9-16)20(24)25/h1-3,5-6,8-11,18-19H,4,7,12-14,23H2,(H3,24,25)(H,26,28)/t18-,19+/m1/s1
• InChIKey: VZFTWWJAUZOJDH-MOPGFXCFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2R)-2-amino-3-phenylpropanoyl]-N-[(4-carbamimidoylphenyl)methyl]pyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S)-1-[(2R)-2-amino-3-phenylpropanoyl]-N-[(4-carbamimidoylphenyl)methyl]pyrrolidine-2-carboxamide
• Synonyms: D-phenylalanyl-N-{4-[amino(iminio)methyl]benzyl}-L-prolinamide

Database IDs

• PubChem SID: 160968090; 99443476
• PubChem CID: 46937043; 10453194

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.242097
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.6844647
• LogD (pH = 7.4): -2.0075011
• Log P: 0.87543666
• Molar Refractivity: 123.1068 cm^3
• Polarizability: 43.39849 Å^3
• Polar Surface Area: 125.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.1
• LOG S: -4.51
• Solubility (Water): 1.32e-02 g/l

DETAILS

DrugBank - DB07005

Drug information: experimental