(2S)-2-[(2S)-2-[(2R)-2-amino-3-phenylpropanamido]-3-phenylpropanamido]-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pentanamide

• ChemBase ID: 106316
• Molecular Formular: C34H36F3N7O5
• Molecular Mass: 679.6887496
• Monoisotopic Mass: 679.27300195
• SMILES: N[C@H](Cc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H](NC(=O)[C@@H](Cc1ccccc1)N)Cc1ccccc1
• InChI: InChI=1S/C34H36F3N7O5/c35-34(36,37)24-19-29(45)49-28-18-22(13-14-23(24)28)42-31(47)26(12-7-15-41-33(39)40)43-32(48)27(17-21-10-5-2-6-11-21)44-30(46)25(38)16-20-8-3-1-4-9-20/h1-6,8-11,13-14,18-19,25-27H,7,12,15-17,38H2,(H,42,47)(H,43,48)(H,44,46)(H4,39,40,41)/t25-,26+,27+/m1/s1
• InChIKey: POSZCLKAGGXYDP-PVHODMMVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2R)-2-amino-3-phenylpropanamido]-3-phenylpropanamido]-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pentanamide
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2R)-2-amino-3-phenylpropanamido]-3-phenylpropanamido]-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]pentanamide
• Synonyms: D-Phe-Phe-Arg-AFC; D-FFR-AFC; D-Phe-Phe-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105393
• PubChem CID: 25108536

CALCULATED PROPERTIES

• Acid pKa: 12.039099
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -1.9072863
• LogD (pH = 7.4): -0.23188388
• Log P: 2.1713
• Molar Refractivity: 186.7383 cm^3
• Polarizability: 66.21218 Å^3
• Polar Surface Area: 201.52 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC060

A fluorogenic substrate for Plasma Kallikrein.