(3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-4-oxobutanoic acid

• ChemBase ID: 106375
• Molecular Formular: C23H32N4O8
• Molecular Mass: 492.52218
• Monoisotopic Mass: 492.222014
• SMILES: CC(C)[C@H](NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C=O
• Canonical SMILES: O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)C)C)CC(=O)O
• InChI: InChI=1S/C23H32N4O8/c1-12(2)20(23(35)24-13(3)21(33)26-16(11-28)10-19(31)32)27-22(34)18(25-14(4)29)9-15-5-7-17(30)8-6-15/h5-8,11-13,16,18,20,30H,9-10H2,1-4H3,(H,24,35)(H,25,29)(H,26,33)(H,27,34)(H,31,32)/t13-,16-,18-,20-/m0/s1
• InChIKey: LPIARALSGDVZEP-SJVNDZIOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-4-oxobutanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-4-oxobutanoic acid
• Synonyms: Ac-Tyr-Val-Ala-Asp-CHO; Ac-YVAD-CHO; Ac-Tyr-Val-Ala-Asp-Aldehyde

Database IDs

• CAS Number: 174063-88-8
• PubChem SID: 162089086
• PubChem CID: 5311139

CALCULATED PROPERTIES

• Acid pKa: 3.8991659
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -2.5361369
• LogD (pH = 7.4): -4.1470156
• Log P: -0.9295936
• Molar Refractivity: 122.538795 cm^3
• Polarizability: 47.84955 Å^3
• Polar Surface Area: 191.0 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AL013

A potent, specific, and reversible inhibitor of caspase-1 (Ki = 200 pM for human recombinant caspase-1), caspase-4, and caspase-5. Strongly inhibits anti-APO-1 induced apoptosis in L929-APO-1 cells.

REFERENCES

• Thornberry, N.A. et al., Nature, 356:768 (1992).
• Erani, M. et al., Nature, 380:723 (1996).
• Garcia-Calvo, M., et al. 1998. J. Biol. Chem. 273, 32608.
• Hilbi, H., et al. 1998. J. Biol. Chem. 273, 32895.
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.
• Los, M., et al. 1995. Nature 375, 81.
• Walker, N.P.C., et al. 1994. Cell 78, 343.
• Wilson, K.P., et al. 1994. Nature 370, 270.