(3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-3-[(4-nitrophenyl)carbamoyl]propanoic acid

• ChemBase ID: 106629
• Molecular Formular: C29H36N6O10
• Molecular Mass: 628.63034
• Monoisotopic Mass: 628.24929138
• 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)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: OC(=O)C[C@@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])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/C29H36N6O10/c1-15(2)25(34-28(42)22(31-17(4)36)13-18-5-11-21(37)12-6-18)29(43)30-16(3)26(40)33-23(14-24(38)39)27(41)32-19-7-9-20(10-8-19)35(44)45/h5-12,15-16,22-23,25,37H,13-14H2,1-4H3,(H,30,43)(H,31,36)(H,32,41)(H,33,40)(H,34,42)(H,38,39)/t16-,22-,23-,25-/m0/s1
• InChIKey: YDPNOCSPPGFBPX-XNHCRPTKSA-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-nitrophenyl)carbamoyl]propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-(4-hydroxyphenyl)propanamido]-3-methylbutanamido]propanamido]-3-[(4-nitrophenyl)carbamoyl]propanoic acid
• Synonyms: Ac-Tyr-Val-Ala-Asp-PNA; Ac-Y-V-A-D-PNA; Ac-Tyr-Val-Ala-Asp-paranitroanilide

Database IDs

• PubChem SID: 162105972
• PubChem CID: 10484117

CALCULATED PROPERTIES

• Acid pKa: 3.5678482
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -1.3230934
• LogD (pH = 7.4): -2.754098
• Log P: 0.60330874
• Molar Refractivity: 159.0662 cm^3
• Polarizability: 60.48565 Å^3
• Polar Surface Area: 248.85 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA120

A colorimetric substrate for Caspase-1. Sequence is based on the caspase-1 cleavage site of the IL-1b precursor and includes Asp116. Also a substrate for caspase-4. Cleavage of pNA is monitored colorimetrically at ~405 nm (e = 9,160 M^-1cm^-1).

REFERENCES

• Marcelli, M. et al., Cancer Res., 58:76 (1998).
• Thornberry, N.A., and Lazebnik, Y. 1998. Science 281, 1312.
• Reiter, L.A. 1994. Int. J. Pept. Protein Res. 43, 87.
• Thornberry, N.A., et al. 1994. Methods Enzymol. 244, 615.
• Thornberry, N.A., et al. 1992. Nature 356, 768.