(3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-3-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]propanoic acid

• ChemBase ID: 106435
• Molecular Formular: C33H39N5O10
• Molecular Mass: 665.69026
• Monoisotopic Mass: 665.26969247
• 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)Nc1ccc2c(c1)oc(=O)cc2C
• Canonical SMILES: OC(=O)C[C@@H](C(=O)Nc1ccc2c(c1)oc(=O)cc2C)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)C)C
• InChI: InChI=1S/C33H39N5O10/c1-16(2)29(38-32(46)24(35-19(5)39)13-20-6-9-22(40)10-7-20)33(47)34-18(4)30(44)37-25(15-27(41)42)31(45)36-21-8-11-23-17(3)12-28(43)48-26(23)14-21/h6-12,14,16,18,24-25,29,40H,13,15H2,1-5H3,(H,34,47)(H,35,39)(H,36,45)(H,37,44)(H,38,46)(H,41,42)/t18-,24-,25-,29-/m0/s1
• InChIKey: YGLOALWHJIANIH-PQTMRPCPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-3-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-3-[(4-methyl-2-oxochromen-7-yl)carbamoyl]propanoic acid
• Synonyms: Ac-Tyr-Val-Ala-Asp-AMC; Ac-YVAD-AMC; Ac-Tyr-Val-Ala-Asp-7-Amino-4-Methylcoumarin

Database IDs

• CAS Number: 149231-65-2
• PubChem SID: 162089021
• PubChem CID: 11125214

CALCULATED PROPERTIES

• Acid pKa: 3.697657
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -1.0282798
• LogD (pH = 7.4): -2.5369918
• Log P: 0.77283293
• Molar Refractivity: 171.5141 cm^3
• Polarizability: 65.76104 Å^3
• Polar Surface Area: 229.33 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03AMC120

A fluorogenic substrate for Caspase-1 (ICE). (Km = 8 μM for human recombinant caspase-1). Also a substrate for caspase-4.

REFERENCES

• Marcelli, M. et al., Cancer Res., 58:76 (1998).
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.
• Walker, N.P.C., et al. 1994. Cell 78, 343.
• Thornberry, N.A., et al. 1992. Nature 356, 768.