tert-butyl N-[(2R)-1-[(2S)-2-{[(R)-(4-carbamimidoylphenyl)(diphenoxyphosphoryl)methyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate

• ChemBase ID: 106486
• Molecular Formular: C39H44N5O7P
• Molecular Mass: 725.769721
• Monoisotopic Mass: 725.2978354
• SMILES: CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=O)N[C@@H](c1ccc(cc1)C(=N)N)P(=O)(Oc1ccccc1)Oc1ccccc1
• Canonical SMILES: O=C(OC(C)(C)C)N[C@@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](P(=O)(Oc1ccccc1)Oc1ccccc1)c1ccc(cc1)C(=N)N)Cc1ccccc1
• InChI: InChI=1S/C39H44N5O7P/c1-39(2,3)49-38(47)42-32(26-27-14-7-4-8-15-27)37(46)44-25-13-20-33(44)35(45)43-36(29-23-21-28(22-24-29)34(40)41)52(48,50-30-16-9-5-10-17-30)51-31-18-11-6-12-19-31/h4-12,14-19,21-24,32-33,36H,13,20,25-26H2,1-3H3,(H3,40,41)(H,42,47)(H,43,45)/t32-,33+,36-/m1/s1
• InChIKey: YEJHEMWKCQGGRY-RWTOGVPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2R)-1-[(2S)-2-{[(R)-(4-carbamimidoylphenyl)(diphenoxyphosphoryl)methyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2R)-1-[(2S)-2-{[(R)-(4-carbamimidoylphenyl)(diphenoxyphosphoryl)methyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate
• Synonyms: Boc-D-Phe-Pro-(4-AmPhGly)p(OPh)2;; Boc-D-Phe-Pro-(4-AmPhGly)p(OPh)2

Database IDs

• PubChem SID: 162105480
• PubChem CID: 25108664

CALCULATED PROPERTIES

• Acid pKa: 11.755722
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 3.287525
• LogD (pH = 7.4): 3.3022497
• Log P: 5.193671
• Molar Refractivity: 206.911 cm^3
• Polarizability: 76.80662 Å^3
• Polar Surface Area: 173.14 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03DAP013

A specific Serine protease inhibitor for Thrombin.

REFERENCES

• Oleksyszyn, J. et al., J. Med. Chem. 1994, 37, 226-231
• Hof, P. et al., EMBO J., 25(20):5481 (1996).