(3S)-3-{[(1S)-3-carbamoyl-1-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}propyl]carbamoyl}-3-acetamidopropanoic acid

• ChemBase ID: 106635
• Molecular Formular: C26H35N7O12S
• Molecular Mass: 669.6608
• Monoisotopic Mass: 669.2064406
• SMILES: CSCC[C@H](NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)O)NC(=O)C)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: CSCC[C@@H](C(=O)N[C@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])CC(=O)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(=O)O)CCC(=O)N
• InChI: InChI=1S/C26H35N7O12S/c1-13(34)28-18(11-21(36)37)26(43)30-16(7-8-20(27)35)23(40)31-17(9-10-46-2)24(41)32-19(12-22(38)39)25(42)29-14-3-5-15(6-4-14)33(44)45/h3-6,16-19H,7-12H2,1-2H3,(H2,27,35)(H,28,34)(H,29,42)(H,30,43)(H,31,40)(H,32,41)(H,36,37)(H,38,39)/t16-,17-,18-,19-/m0/s1
• InChIKey: JKYQLEISVBYLOC-VJANTYMQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-3-carbamoyl-1-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}propyl]carbamoyl}-3-acetamidopropanoic acid
• IUPAC Traditional name: (3S)-3-{[(1S)-3-carbamoyl-1-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-3-(methylsulfanyl)propyl]carbamoyl}propyl]carbamoyl}-3-acetamidopropanoic acid
• Synonyms: Ac-Asp-Gln-Met-Asp-PNA; Ac-DQMD-PNA; Ac-Asp-Gln-Met-Asp-paranitroanilide

Database IDs

• PubChem SID: 162105557
• PubChem CID: 25108785

CALCULATED PROPERTIES

• Acid pKa: 3.4297748
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -6.2638345
• LogD (pH = 7.4): -9.329577
• Log P: -2.7874243
• Molar Refractivity: 159.2074 cm^3
• Polarizability: 60.86617 Å^3
• Polar Surface Area: 309.01 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA144

A colorimetric substrate for Caspase-3 and 6.

REFERENCES

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Thornberry, N.A. et al., J. Biol. Chem., 272:17907 (1997).