(4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-acetamidopropanamido]butanoic acid

• ChemBase ID: 106636
• Molecular Formular: C25H34N6O11
• Molecular Mass: 594.57106
• Monoisotopic Mass: 594.22855594
• SMILES: CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C)NC(=O)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](C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)C)CCC(=O)O
• InChI: InChI=1S/C25H34N6O11/c1-12(2)21(30-23(38)17(9-10-19(33)34)28-22(37)13(3)26-14(4)32)25(40)29-18(11-20(35)36)24(39)27-15-5-7-16(8-6-15)31(41)42/h5-8,12-13,17-18,21H,9-11H2,1-4H3,(H,26,32)(H,27,39)(H,28,37)(H,29,40)(H,30,38)(H,33,34)(H,35,36)/t13-,17-,18-,21-/m0/s1
• InChIKey: BKZWKAJKSQIGBP-DGJUNBOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-acetamidopropanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-2-acetamidopropanamido]butanoic acid
• Synonyms: Ac-Ala-Glu-Val-Asp-PNA; Ac-AEVD-PNA; Ac-Ala-Glu-Val-Asp-paranitroanilide

Database IDs

• PubChem SID: 162106020
• PubChem CID: 25108786

CALCULATED PROPERTIES

• Acid pKa: 3.5694375
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -4.2713494
• LogD (pH = 7.4): -7.4789
• Log P: -1.102603
• Molar Refractivity: 143.2567 cm^3
• Polarizability: 54.664047 Å^3
• Polar Surface Area: 265.92 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA145

A colorimetric substrate for Caspase-6, 8 and 10.

REFERENCES

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Thornberry, N.A. et al., J. Biol. Chem., 272:17907 (1997).