3-{[(2S)-1-[(2S)-2-{[(2S)-1-(benzylsulfanyl)-1-oxo-3-phenylpropan-2-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}propanoic acid

• ChemBase ID: 106673
• Molecular Formular: C28H33N3O6S
• Molecular Mass: 539.64312
• Monoisotopic Mass: 539.20900679
• SMILES: C[C@H](NC(=O)CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1ccccc1)C(=O)SCc1ccccc1
• Canonical SMILES: O=C(N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)SCc1ccccc1)Cc1ccccc1)C)CCC(=O)O
• InChI: InChI=1S/C28H33N3O6S/c1-19(29-24(32)14-15-25(33)34)27(36)31-16-8-13-23(31)26(35)30-22(17-20-9-4-2-5-10-20)28(37)38-18-21-11-6-3-7-12-21/h2-7,9-12,19,22-23H,8,13-18H2,1H3,(H,29,32)(H,30,35)(H,33,34)/t19-,22-,23-/m0/s1
• InChIKey: NQEVGMPXBFRBPE-VJBMBRPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(2S)-1-[(2S)-2-{[(2S)-1-(benzylsulfanyl)-1-oxo-3-phenylpropan-2-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[(2S)-1-[(2S)-2-{[(2S)-1-(benzylsulfanyl)-1-oxo-3-phenylpropan-2-yl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}propanoic acid
• Synonyms: Suc-Ala-Pro-Phe-Thiobenzyl Ester; Suc-APF-Thiobenzyl Ester; Suc-Ala-Pro-Phe-Thiobenzyl Ester

Database IDs

• PubChem SID: 162106023
• PubChem CID: 25108818

CALCULATED PROPERTIES

• Acid pKa: 4.063712
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.99375296
• LogD (pH = 7.4): -0.6792309
• Log P: 2.4421706
• Molar Refractivity: 143.4639 cm^3
• Polarizability: 56.013103 Å^3
• Polar Surface Area: 132.88 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

REFERENCES

• Odeegard, O.R., Try, K. et al., Homeostasis, 17:109 (1987).
• Yoshida, N. et al., Biochem., 19:5799 (1980).