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

• ChemBase ID: 106490
• Molecular Formular: C36H43N4O9P
• Molecular Mass: 706.721781
• Monoisotopic Mass: 706.27676561
• 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](Cc1ccccc1)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)Cc1ccccc1)C)C
• InChI: InChI=1S/C36H43N4O9P/c1-25(37-31(41)21-22-33(42)47-3)34(43)38-26(2)36(45)40-23-13-20-30(40)35(44)39-32(24-27-14-7-4-8-15-27)50(46,48-28-16-9-5-10-17-28)49-29-18-11-6-12-19-29/h4-12,14-19,25-26,30,32H,13,20-24H2,1-3H3,(H,37,41)(H,38,43)(H,39,44)/t25-,26-,30-,32+/m0/s1
• InChIKey: RIMFVOKAUXRHHL-SPBNXANVSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162105623
• PubChem CID: 25108668

CALCULATED PROPERTIES

• Acid pKa: 11.643019
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.0387716
• LogD (pH = 7.4): 3.0387492
• Log P: 3.0387719
• Molar Refractivity: 183.0155 cm^3
• Polarizability: 72.23866 Å^3
• Polar Surface Area: 169.44 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03DAP023

A specific Serine protease inhibitor for Chymotrypsin.

REFERENCES

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