(2S)-6-amino-2-[(2S)-2-[(2R)-2-amino-3-methylbutanamido]-4-methylpentanamido]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]hexanamide

• ChemBase ID: 106324
• Molecular Formular: C27H38F3N5O5
• Molecular Mass: 569.6163296
• Monoisotopic Mass: 569.282504
• SMILES: CC(C)C[C@H](NC(=O)[C@H](N)C(C)C)C(=O)N[C@@H](CCCCN)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: NCCCC[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@@H](NC(=O)[C@@H](C(C)C)N)CC(C)C
• InChI: InChI=1S/C27H38F3N5O5/c1-14(2)11-20(35-26(39)23(32)15(3)4)25(38)34-19(7-5-6-10-31)24(37)33-16-8-9-17-18(27(28,29)30)13-22(36)40-21(17)12-16/h8-9,12-15,19-20,23H,5-7,10-11,31-32H2,1-4H3,(H,33,37)(H,34,38)(H,35,39)/t19-,20-,23+/m0/s1
• InChIKey: BZABHENLDPLCOR-SXWKCWPCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-[(2S)-2-[(2R)-2-amino-3-methylbutanamido]-4-methylpentanamido]-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]hexanamide
• IUPAC Traditional name: (2S)-6-amino-2-[(2S)-2-[(2R)-2-amino-3-methylbutanamido]-4-methylpentanamido]-N-[2-oxo-4-(trifluoromethyl)chromen-7-yl]hexanamide
• Synonyms: D-Val-Leu-Lys-AFC; D-VLK-AFC; D-Val-Leu-Lys-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105949
• PubChem CID: 25108544

CALCULATED PROPERTIES

• Acid pKa: 11.78771
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -3.3021624
• LogD (pH = 7.4): -1.2097899
• Log P: 2.13877
• Molar Refractivity: 144.0559 cm^3
• Polarizability: 54.811653 Å^3
• Polar Surface Area: 165.64 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC081

HYGROSCOPIC. A fluorogenic substrate for Plasmin.

REFERENCES

• Calvin, S.A. et al., Anal. Biochem., 80:355 (1977).
• Kato, H. et al., Biochem., 88:183 (1980).