methyl 3-{[(1S)-1-{[(1S)-1-{[(1R)-1-(diphenoxyphosphoryl)-2-phenylethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}propanoate

• ChemBase ID: 106488
• Molecular Formular: C31H36N3O8P
• Molecular Mass: 609.606601
• Monoisotopic Mass: 609.22400176
• SMILES: COC(=O)CCC(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)P(=O)(Oc1ccccc1)Oc1ccccc1
• Canonical SMILES: COC(=O)CCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](P(=O)(Oc1ccccc1)Oc1ccccc1)Cc1ccccc1)C)C
• InChI: InChI=1S/C31H36N3O8P/c1-22(32-27(35)19-20-29(36)40-3)30(37)33-23(2)31(38)34-28(21-24-13-7-4-8-14-24)43(39,41-25-15-9-5-10-16-25)42-26-17-11-6-12-18-26/h4-18,22-23,28H,19-21H2,1-3H3,(H,32,35)(H,33,37)(H,34,38)/t22-,23-,28+/m0/s1
• InChIKey: JTEQJXYVSHQRQN-UXWDXCIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 3-{[(1S)-1-{[(1S)-1-{[(1R)-1-(diphenoxyphosphoryl)-2-phenylethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}propanoate
• IUPAC Traditional name: methyl 3-{[(1S)-1-{[(1S)-1-{[(1R)-1-(diphenoxyphosphoryl)-2-phenylethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}propanoate
• Synonyms: MeOSuc-Ala-Ala-Phep(OPh)2; MeOSuc-AA-Phep(OPh)2; MeOSuc-Ala-Ala-Phep(OPh)2

Database IDs

• PubChem SID: 162105989
• PubChem CID: 25108666

CALCULATED PROPERTIES

• Acid pKa: 11.644596
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.285546
• LogD (pH = 7.4): 3.2855237
• Log P: 3.2855463
• Molar Refractivity: 158.029 cm^3
• Polarizability: 62.52703 Å^3
• Polar Surface Area: 149.13 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03DAP022

A specific Serine protease inhibitor for Cathepsin G and Chymotrypsin.

REFERENCES

• Oleksyszyn, J. and Powers, J.C., Methods in Enzymology, 244:423 (1994).