(3S)-3-[(2S)-2-[(2S)-4-carbamoyl-2-[(2S)-2-acetamido-3-methylbutanamido]butanamido]-3-methylbutanamido]-3-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}propanoic acid

• ChemBase ID: 106366
• Molecular Formular: C31H39F3N6O10
• Molecular Mass: 712.6707696
• Monoisotopic Mass: 712.26797614
• SMILES: CC(C)[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F
• Canonical SMILES: OC(=O)C[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C(F)(F)F)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)C)CCC(=O)N
• InChI: InChI=1S/C31H39F3N6O10/c1-13(2)25(36-15(5)41)29(48)38-19(8-9-22(35)42)27(46)40-26(14(3)4)30(49)39-20(12-23(43)44)28(47)37-16-6-7-17-18(31(32,33)34)11-24(45)50-21(17)10-16/h6-7,10-11,13-14,19-20,25-26H,8-9,12H2,1-5H3,(H2,35,42)(H,36,41)(H,37,47)(H,38,48)(H,39,49)(H,40,46)(H,43,44)/t19-,20-,25-,26-/m0/s1
• InChIKey: RYVUNXWUXFQDIA-HKDRDPIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-4-carbamoyl-2-[(2S)-2-acetamido-3-methylbutanamido]butanamido]-3-methylbutanamido]-3-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]carbamoyl}propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-4-carbamoyl-2-[(2S)-2-acetamido-3-methylbutanamido]butanamido]-3-methylbutanamido]-3-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]carbamoyl}propanoic acid
• Synonyms: Ac-Val-Gln-Val-Asp-AFC; Ac-VQVD-AFC; Ac-Val-Gln-Val-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105418
• PubChem CID: 25108585

CALCULATED PROPERTIES

• Acid pKa: 3.7849464
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -2.204846
• LogD (pH = 7.4): -3.7573717
• Log P: -0.4880991
• Molar Refractivity: 167.4549 cm^3
• Polarizability: 63.67468 Å^3
• Polar Surface Area: 252.19 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC201

A fluorogenic substrate for Caspase-6.

REFERENCES

• Talanian, R.V. et al., J. Biol. Chem., 272(15):9677 (1997)