(2S)-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]-2-[(2S)-3-phenyl-2-[(2R)-pyrrolidin-2-ylformamido]propanamido]pentanamide

• ChemBase ID: 106315
• Molecular Formular: C30H34F3N7O5
• Molecular Mass: 629.6300696
• Monoisotopic Mass: 629.25735188
• SMILES: NC(=N)NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H]1NCCC1)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](Cc1ccccc1)NC(=O)[C@H]1CCCN1
• InChI: InChI=1S/C30H34F3N7O5/c31-30(32,33)20-16-25(41)45-24-15-18(10-11-19(20)24)38-27(43)22(9-5-13-37-29(34)35)39-28(44)23(14-17-6-2-1-3-7-17)40-26(42)21-8-4-12-36-21/h1-3,6-7,10-11,15-16,21-23,36H,4-5,8-9,12-14H2,(H,38,43)(H,39,44)(H,40,42)(H4,34,35,37)/t21-,22+,23+/m1/s1
• InChIKey: MHQPHRLBFDGNQY-VJBWXMMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]-2-[(2S)-3-phenyl-2-[(2R)-pyrrolidin-2-ylformamido]propanamido]pentanamide
• IUPAC Traditional name: (2S)-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]-2-[(2S)-3-phenyl-2-[(2R)-pyrrolidin-2-ylformamido]propanamido]pentanamide
• Synonyms: D-Pro-Phe-Arg-AFC; D-PFR-AFC; D-Pro-Phe-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105392
• PubChem CID: 25108535

CALCULATED PROPERTIES

• Acid pKa: 12.0127735
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -4.1042633
• LogD (pH = 7.4): -3.0033069
• Log P: 0.97811216
• Molar Refractivity: 169.6863 cm^3
• Polarizability: 59.663708 Å^3
• Polar Surface Area: 187.53 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC059

HYGROSCOPIC. A fluorogenic substrate for Thrombin.

REFERENCES

• McRae, B.J. et al., Biochem., 20:7196 (1981).
• Kato, H. et al., Throm. Res., 56:77 (1988).