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

• ChemBase ID: 106377
• Molecular Formular: C23H34N6O9
• Molecular Mass: 538.55086
• Monoisotopic Mass: 538.2387267
• SMILES: CC(C)C[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CC(=O)O)C=O
• Canonical SMILES: O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(C)C)CCC(=O)O)Cc1nc[nH]c1)CC(=O)O
• InChI: InChI=1S/C23H34N6O9/c1-12(2)6-17(26-13(3)31)23(38)28-16(4-5-19(32)33)21(36)29-18(7-14-9-24-11-25-14)22(37)27-15(10-30)8-20(34)35/h9-12,15-18H,4-8H2,1-3H3,(H,24,25)(H,26,31)(H,27,37)(H,28,38)(H,29,36)(H,32,33)(H,34,35)/t15-,16-,17-,18-/m0/s1
• InChIKey: LRHHFDQCXBPQLY-XSLAGTTESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(2S)-1-carboxy-3-oxopropan-2-yl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]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-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: Ac-Leu-Glu-His-Asp-CHO; Ac-LEHD-CHO; Ac-Leu-Glu-His-Asp-Aldehyde

Database IDs

• PubChem SID: 162105421
• PubChem CID: 10256708

CALCULATED PROPERTIES

• Acid pKa: 3.4522417
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -5.462402
• LogD (pH = 7.4): -8.009053
• Log P: -4.14552
• Molar Refractivity: 128.4033 cm^3
• Polarizability: 50.259644 Å^3
• Polar Surface Area: 236.75 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AL022

An inhibitor for Caspase-9.

REFERENCES

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