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

• ChemBase ID: 106380
• Molecular Formular: C22H36N4O9
• Molecular Mass: 500.54264
• Monoisotopic Mass: 500.24822875
• SMILES: CC(C)C[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](C(C)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(C)C)CCC(=O)O)CC(=O)O
• InChI: InChI=1S/C22H36N4O9/c1-11(2)8-16(23-13(5)28)21(34)25-15(6-7-17(29)30)20(33)26-19(12(3)4)22(35)24-14(10-27)9-18(31)32/h10-12,14-16,19H,6-9H2,1-5H3,(H,23,28)(H,24,35)(H,25,34)(H,26,33)(H,29,30)(H,31,32)/t14-,15-,16-,19-/m0/s1
• InChIKey: MXGJLIBJKIIQSF-FPXQBCRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(2S)-1-carboxy-3-oxopropan-2-yl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(2S)-1-carboxy-3-oxopropan-2-yl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: Ac-Leu-Glu-Val-Asp-CHO; Ac-LEVD-CHO; Ac-Leu-Glu-Val-Asp-Aldehyde

Database IDs

• PubChem SID: 162105424
• PubChem CID: 11225800

CALCULATED PROPERTIES

• Acid pKa: 3.75728
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -4.288519
• LogD (pH = 7.4): -7.6307125
• Log P: -1.3813952
• Molar Refractivity: 120.4029 cm^3
• Polarizability: 47.48038 Å^3
• Polar Surface Area: 208.07 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AL026

A reversible inhibitor for Caspase-4.

REFERENCES

• Thornberry, N.A. and Lazebnik, K. et al., Science 281:1312 (1995).
• Talanian, R.V. et al., J. Biol. Chem., 272:9677 (1997).