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

• ChemBase ID: 106641
• Molecular Formular: C34H37N9O11
• Molecular Mass: 747.71128
• Monoisotopic Mass: 747.26125305
• SMILES: CC(=O)N[C@@H](Cc1c[nH]c2c1cccc2)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)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])CC(=O)O)Cc1c[nH]cn1)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)C
• InChI: InChI=1S/C34H37N9O11/c1-18(44)38-26(12-19-15-36-24-5-3-2-4-23(19)24)33(51)40-25(10-11-29(45)46)31(49)41-27(13-21-16-35-17-37-21)34(52)42-28(14-30(47)48)32(50)39-20-6-8-22(9-7-20)43(53)54/h2-9,15-17,25-28,36H,10-14H2,1H3,(H,35,37)(H,38,44)(H,39,50)(H,40,51)(H,41,49)(H,42,52)(H,45,46)(H,47,48)/t25-,26-,27-,28-/m0/s1
• InChIKey: FDGCMTAKGVLJGO-LJWNLINESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-acetamido-3-(1H-indol-3-yl)propanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-(1H-imidazol-4-yl)ethyl]carbamoyl}-4-[(2S)-2-acetamido-3-(1H-indol-3-yl)propanamido]butanoic acid
• Synonyms: Ac-Trp-Glu-His-Asp-PNA; Ac-WEHD-PNA; Ac-Trp-Glu-His-Asp-paranitroanilide

Database IDs

• PubChem SID: 162105559
• PubChem CID: 25108790

CALCULATED PROPERTIES

• Acid pKa: 3.3459187
• H Acceptors: 12
• H Donor: 9
• LogD (pH = 5.5): -3.4354436
• LogD (pH = 7.4): -5.9786954
• Log P: -2.1333184
• Molar Refractivity: 186.9626 cm^3
• Polarizability: 72.00979 Å^3
• Polar Surface Area: 310.39 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA156

A colorimetric substrate for Caspase-1.

REFERENCES

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