(4S)-4-[(2S)-3-carboxy-2-acetamidopropanamido]-4-{[(1S)-1-{[(2S)-1-carboxy-3-oxopropan-2-yl]carbamoyl}-2-methylpropyl]carbamoyl}butanoic acid

• ChemBase ID: 106373
• Molecular Formular: C20H30N4O11
• Molecular Mass: 502.4724
• Monoisotopic Mass: 502.1911078
• SMILES: CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)NC(=O)C)C(=O)N[C@@H](CC(=O)O)C=O
• Canonical SMILES: O=C[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(=O)O)CCC(=O)O)CC(=O)O
• InChI: InChI=1S/C20H30N4O11/c1-9(2)17(20(35)22-11(8-25)6-15(29)30)24-18(33)12(4-5-14(27)28)23-19(34)13(7-16(31)32)21-10(3)26/h8-9,11-13,17H,4-7H2,1-3H3,(H,21,26)(H,22,35)(H,23,34)(H,24,33)(H,27,28)(H,29,30)(H,31,32)/t11-,12-,13-,17-/m0/s1
• InChIKey: UMBVAPCONCILTL-MRHIQRDNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(2S)-3-carboxy-2-acetamidopropanamido]-4-{[(1S)-1-{[(2S)-1-carboxy-3-oxopropan-2-yl]carbamoyl}-2-methylpropyl]carbamoyl}butanoic acid
• IUPAC Traditional name: ac-devd-cho
• Synonyms: Ac-Asp-Glu-Val-Asp-CHO; Ac-DEVD-CHO; Ac-Asp-Glu-Val-Asp-Aldehyde

Database IDs

• CAS Number: 169332-60-9
• PubChem SID: 162087683
• PubChem CID: 644345

CALCULATED PROPERTIES

• Acid pKa: 3.4770713
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -7.8290443
• LogD (pH = 7.4): -12.740356
• Log P: -3.2773173
• Molar Refractivity: 112.7647 cm^3
• Polarizability: 44.55075 Å^3
• Polar Surface Area: 245.37 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AL010

A very potent, specific, and reversible inhibitor of caspase-3 (IC₅₀ = 200 pM), caspase-6, caspase-7, caspase-8, and caspase-10.

REFERENCES

• Garcia-Calvo, M. et al., J. Biol. Chem., 273:32608 (1998).
• Thornberry, N.A. and Lazebnik, Y. et al., Science, 281:1312 (1998).
• Nicholson, D.W. et al., Nature Biotech., 14:297 (1996).
• Schlegel, J., et al. 1996. J. Biol. Chem. 271, 1841.
• Nicholson, D.W., et al. 1995. Nature 376, 37.