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

• ChemBase ID: 106341
• Molecular Formular: C31H42F3N7O7
• Molecular Mass: 681.7030896
• Monoisotopic Mass: 681.30978138
• SMILES: CC(C)[C@H](NC(=O)OC(C)(C)C)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](C(C)C)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C31H42F3N7O7/c1-16(2)24(40-29(46)48-30(3,4)5)27(45)41-13-7-9-21(41)26(44)39-20(8-6-12-37-28(35)36)25(43)38-17-10-11-18-19(31(32,33)34)15-23(42)47-22(18)14-17/h10-11,14-16,20-21,24H,6-9,12-13H2,1-5H3,(H,38,43)(H,39,44)(H,40,46)(H4,35,36,37)/t20-,21-,24-/m0/s1
• InChIKey: JKZJETOUASXVSN-HFMPRLQTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2S)-1-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2S)-1-[(2S)-2-{[(1S)-4-carbamimidamido-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}butyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
• Synonyms: Boc-Val-Pro-Arg-AFC; Boc-VPR-AFC; Boc-Val-Pro-Arg-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105956
• PubChem CID: 25108561

CALCULATED PROPERTIES

• Acid pKa: 11.463695
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -0.41686743
• LogD (pH = 7.4): -0.41022587
• Log P: 1.5318793
• Molar Refractivity: 179.058 cm^3
• Polarizability: 63.482937 Å^3
• Polar Surface Area: 205.04 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC118

A specific fluorogenic substrate for Thrombin.

REFERENCES

• Mizuno, K. et al., Biochem. Biophys. Res. Comm., 159:305 (1989).
• Kawabata, S. et al., Eur. J. Biochem., 172:17 (1988).