methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1R)-1-(diphenoxyphosphoryl)-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate

• ChemBase ID: 106487
• Molecular Formular: C32H43N4O9P
• Molecular Mass: 658.678981
• Monoisotopic Mass: 658.27676561
• SMILES: COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)P(=O)(Oc1ccccc1)Oc1ccccc1
• Canonical SMILES: COC(=O)CCC(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](P(=O)(Oc1ccccc1)Oc1ccccc1)C(C)C)C)C
• InChI: InChI=1S/C32H43N4O9P/c1-21(2)31(46(42,44-24-13-8-6-9-14-24)45-25-15-10-7-11-16-25)35-30(40)26-17-12-20-36(26)32(41)23(4)34-29(39)22(3)33-27(37)18-19-28(38)43-5/h6-11,13-16,21-23,26,31H,12,17-20H2,1-5H3,(H,33,37)(H,34,39)(H,35,40)/t22-,23-,26-,31+/m0/s1
• InChIKey: HVXLEJKJZYYKKT-PGNPNZOKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1R)-1-(diphenoxyphosphoryl)-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate
• IUPAC Traditional name: methyl 3-{[(1S)-1-{[(2S)-1-[(2S)-2-{[(1R)-1-(diphenoxyphosphoryl)-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-1-oxopropan-2-yl]carbamoyl}ethyl]carbamoyl}propanoate
• Synonyms: MeOSuc-Ala-Ala-Pro-Valp(OPh)2; MeOSuc-AAP-Valp(OPh)2; MeOSuc-Ala-Ala-Pro-Valp(OPh)2

Database IDs

• PubChem SID: 162105481
• PubChem CID: 25108665

CALCULATED PROPERTIES

• Acid pKa: 11.691001
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.363147
• LogD (pH = 7.4): 2.363127
• Log P: 2.3631473
• Molar Refractivity: 167.3369 cm^3
• Polarizability: 66.37035 Å^3
• Polar Surface Area: 169.44 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03DAP020

A specific Serine protease inhibitor for Elastase.

REFERENCES

• Oleksyszyn, J. and Powers, J.C., Biochemistry, 30:485.