benzyl N-[(2S)-1-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate

• ChemBase ID: 106311
• Molecular Formular: C38H40F3N7O7
• Molecular Mass: 763.7621096
• Monoisotopic Mass: 763.29413132
• SMILES: NC(=N)NCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: O=C(N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)CCCNC(=N)N)Cc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C38H40F3N7O7/c39-38(40,41)27-21-32(49)55-31-20-25(15-16-26(27)31)45-33(50)28(13-7-17-44-36(42)43)46-34(51)30-14-8-18-48(30)35(52)29(19-23-9-3-1-4-10-23)47-37(53)54-22-24-11-5-2-6-12-24/h1-6,9-12,15-16,20-21,28-30H,7-8,13-14,17-19,22H2,(H,45,50)(H,46,51)(H,47,53)(H4,42,43,44)/t28-,29-,30-/m0/s1
• InChIKey: JVPSZQQPARBPOQ-DTXPUJKBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(2S)-1-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate
• IUPAC Traditional name: benzyl N-[(2S)-1-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate
• Synonyms: Z-Phe-Pro-Arg-AFC; Z-FPR-AFC; Z-Phe-Pro-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105571
• PubChem CID: 25108532

CALCULATED PROPERTIES

• Acid pKa: 11.51084
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): 1.0224702
• LogD (pH = 7.4): 1.0285769
• Log P: 2.981991
• Molar Refractivity: 205.4884 cm^3
• Polarizability: 73.30794 Å^3
• Polar Surface Area: 205.04 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC054

A fluorogenic substrate for Kallikrein.

REFERENCES

• Magihara, M. et al., Clin. Chem., 33:1463 (1987).