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

• ChemBase ID: 106340
• Molecular Formular: C29H30F3N3O8
• Molecular Mass: 605.5590096
• Monoisotopic Mass: 605.1984996
• SMILES: CC(C)C[C@H](NC(=O)CCC(=O)O)C(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: CC(C[C@@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)Cc1ccc(cc1)O)NC(=O)CCC(=O)O)C
• InChI: InChI=1S/C29H30F3N3O8/c1-15(2)11-21(34-24(37)9-10-25(38)39)28(42)35-22(12-16-3-6-18(36)7-4-16)27(41)33-17-5-8-19-20(29(30,31)32)14-26(40)43-23(19)13-17/h3-8,13-15,21-22,36H,9-12H2,1-2H3,(H,33,41)(H,34,37)(H,35,42)(H,38,39)/t21-,22-/m0/s1
• InChIKey: YDXOCKKOEMXDBL-VXKWHMMOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1S)-1-{[(1S)-2-(4-hydroxyphenyl)-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}propanoic acid
• IUPAC Traditional name: 3-{[(1S)-1-{[(1S)-2-(4-hydroxyphenyl)-1-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}ethyl]carbamoyl}-3-methylbutyl]carbamoyl}propanoic acid
• Synonyms: Suc-Leu-Tyr-AFC; Suc-LY-AFC; Suc-Leu-Tyr-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105402
• PubChem CID: 25108560

CALCULATED PROPERTIES

• Acid pKa: 4.3265214
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 1.8437846
• LogD (pH = 7.4): 0.09664765
• Log P: 3.0435877
• Molar Refractivity: 147.3877 cm^3
• Polarizability: 55.271152 Å^3
• Polar Surface Area: 171.13 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC117

A fluorogenic substrate for Porcine Calpain Isozymes I and II.

REFERENCES

• Sasaki, T. et al., J. Biol. Chem., 259:12489 (1984).
• Woo, K.M. et al., J. Biol. Chem., 264:2088 (1989).