diphenyl [(1R)-1-[(2S)-2-[(2S)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}propanamido]propanamido]-2-phenylethyl]phosphonate

• ChemBase ID: 106489
• Molecular Formular: C36H44N5O7PS
• Molecular Mass: 721.802621
• Monoisotopic Mass: 721.2699064
• SMILES: C[C@H](NC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)P(=O)(Oc1ccccc1)Oc1ccccc1
• Canonical SMILES: O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](P(=O)(Oc1ccccc1)Oc1ccccc1)Cc1ccccc1)C)C)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C36H44N5O7PS/c1-24(37-31(42)21-13-12-20-30-33-29(23-50-30)39-36(45)41-33)34(43)38-25(2)35(44)40-32(22-26-14-6-3-7-15-26)49(46,47-27-16-8-4-9-17-27)48-28-18-10-5-11-19-28/h3-11,14-19,24-25,29-30,32-33H,12-13,20-23H2,1-2H3,(H,37,42)(H,38,43)(H,40,44)(H2,39,41,45)/t24-,25-,29-,30-,32+,33-/m0/s1
• InChIKey: LJEXZMKHWCOTHT-YZVIDYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diphenyl [(1R)-1-[(2S)-2-[(2S)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}propanamido]propanamido]-2-phenylethyl]phosphonate
• IUPAC Traditional name: diphenyl (1R)-1-[(2S)-2-[(2S)-2-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}propanamido]propanamido]-2-phenylethylphosphonate
• Synonyms: Biotin-Ala-Ala-Phep(OPh)2; Biotin-AA-Phep(OPh)2; Biotin-Ala-Ala-Phep(OPh)2

Database IDs

• PubChem SID: 162105499
• PubChem CID: 25108667

CALCULATED PROPERTIES

• Acid pKa: 11.672635
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): 3.921332
• LogD (pH = 7.4): 3.9213114
• Log P: 3.9213324
• Molar Refractivity: 189.7738 cm^3
• Polarizability: 74.91209 Å^3
• Polar Surface Area: 163.96 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03DAP022C

A specific Serine protease inhibitor for Cathepsin G and Chymotrypsin.

REFERENCES

• Abuelyaman, A.S. et al., Arc. Biochem. Biophys., 344(2):271 (1997).