(3S)-3-{[(1S)-1-{[(1S)-3-carbamoyl-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-6-yl]carbamoyl}ethyl]carbamoyl}propyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-3-acetamidopropanoic acid

• ChemBase ID: 106354
• Molecular Formular: C30H35F3N6O12S
• Molecular Mass: 760.6921096
• Monoisotopic Mass: 760.19857625
• SMILES: CSCC[C@H](NC(=O)[C@H](CC(=O)O)NC(=O)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(c1)c(cc(=O)o2)C(F)(F)F
• Canonical SMILES: CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc2c(c1)c(cc(=O)o2)C(F)(F)F)CC(=O)O)CCC(=O)N)NC(=O)[C@@H](NC(=O)C)CC(=O)O
• InChI: InChI=1S/C30H35F3N6O12S/c1-13(40)35-19(11-23(42)43)29(50)38-18(7-8-52-2)27(48)37-17(4-6-22(34)41)26(47)39-20(12-24(44)45)28(49)36-14-3-5-21-15(9-14)16(30(31,32)33)10-25(46)51-21/h3,5,9-10,17-20H,4,6-8,11-12H2,1-2H3,(H2,34,41)(H,35,40)(H,36,49)(H,37,48)(H,38,50)(H,39,47)(H,42,43)(H,44,45)/t17-,18-,19-,20-/m0/s1
• InChIKey: WOPWHQKXAFMGPD-MUGJNUQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-1-{[(1S)-3-carbamoyl-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)-2H-chromen-6-yl]carbamoyl}ethyl]carbamoyl}propyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-3-acetamidopropanoic acid
• IUPAC Traditional name: (3S)-3-{[(1S)-1-{[(1S)-3-carbamoyl-1-{[(1S)-2-carboxy-1-{[2-oxo-4-(trifluoromethyl)chromen-6-yl]carbamoyl}ethyl]carbamoyl}propyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}-3-acetamidopropanoic acid
• Synonyms: Ac-Asp-Met-Gln-Asp-AFC; Ac-DMQDAFC; Ac-Asp-Met-Gln-Asp-7-Amino-4-trifluoromethylcoumarin

Database IDs

• PubChem SID: 162105692
• PubChem CID: 25108573

CALCULATED PROPERTIES

• Acid pKa: 3.4681933
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -5.6371617
• LogD (pH = 7.4): -8.746961
• Log P: -2.253473
• Molar Refractivity: 172.5878 cm^3
• Polarizability: 65.63738 Å^3
• Polar Surface Area: 289.49 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AFC144

A fluorogenic substrate for Caspase-3 and 6.

REFERENCES

• Ekert, P.G. et al., EMBO, 18(2):330 (1999).