3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}-2-phenylethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}propanoic acid

• ChemBase ID: 106326
• Molecular Formular: C29H29F3N4O8
• Molecular Mass: 618.5577696
• Monoisotopic Mass: 618.19374857
• SMILES: C[C@H](NC(=O)CCC(=O)O)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: O=C(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)Cc1ccccc1)C)C)CCC(=O)O
• InChI: InChI=1S/C29H29F3N4O8/c1-15(33-23(37)10-11-24(38)39)26(41)34-16(2)27(42)36-21(12-17-6-4-3-5-7-17)28(43)35-18-8-9-19-20(29(30,31)32)14-25(40)44-22(19)13-18/h3-9,13-16,21H,10-12H2,1-2H3,(H,33,37)(H,34,41)(H,35,43)(H,36,42)(H,38,39)/t15-,16-,21-/m0/s1
• InChIKey: FTICUKXBJSUSQK-QYWGDWMGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}-2-phenylethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[(1S)-1-{[(1S)-1-{[(1S)-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}-2-phenylethyl]carbamoyl}ethyl]carbamoyl}ethyl]carbamoyl}propanoic acid
• Synonyms: Suc-Ala-Ala-Phe-AFC; Suc-AAF-AFC; Suc-Ala-Ala-Phe-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105490
• PubChem CID: 25108546

CALCULATED PROPERTIES

• Acid pKa: 4.0904903
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 0.13370167
• LogD (pH = 7.4): -1.5484015
• Log P: 1.5565238
• Molar Refractivity: 149.0306 cm^3
• Polarizability: 55.920208 Å^3
• Polar Surface Area: 180.0 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC084

A fluorogenic substrate for Cathepsin G.

REFERENCES

• Lively, M. O. et al., Biochem. Biophys. Acta., 525:171 (1978).
• Yoshida, N. et al., Biochem., 19:5799 (1980).