(2S)-2-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pentanamide

• ChemBase ID: 106318
• Molecular Formular: C30H34F3N7O5
• Molecular Mass: 629.6300696
• Monoisotopic Mass: 629.25735188
• SMILES: N[C@H](Cc1ccccc1)C(=O)N1CCC[C@H]1C(=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]1CCCN1C(=O)[C@@H](Cc1ccccc1)N
• InChI: InChI=1S/C30H34F3N7O5/c31-30(32,33)20-16-25(41)45-24-15-18(10-11-19(20)24)38-26(42)22(8-4-12-37-29(35)36)39-27(43)23-9-5-13-40(23)28(44)21(34)14-17-6-2-1-3-7-17/h1-3,6-7,10-11,15-16,21-23H,4-5,8-9,12-14,34H2,(H,38,42)(H,39,43)(H4,35,36,37)/t21-,22+,23+/m1/s1
• InChIKey: CUTJVUQFEGVBFY-VJBWXMMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]pentanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-1-[(2R)-2-amino-3-phenylpropanoyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]pentanamide
• Synonyms: D-Phe-Pro-Arg-AFC; D-FPR-AFC; D-Phe-Pro-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105394
• PubChem CID: 25108538

CALCULATED PROPERTIES

• Acid pKa: 11.546896
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -3.2847037
• LogD (pH = 7.4): -1.6110706
• Log P: 0.84122515
• Molar Refractivity: 169.8084 cm^3
• Polarizability: 59.66371 Å^3
• Polar Surface Area: 192.73 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC064

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).