(3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-[(2S)-2-acetamido-3-methylbutanamido]propanoic acid

• ChemBase ID: 106634
• Molecular Formular: C29H41N7O12
• Molecular Mass: 679.67554
• Monoisotopic Mass: 679.28131979
• SMILES: CC(C)[C@H](NC(=O)C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](C(C)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](NC(=O)[C@H](C(C)C)NC(=O)C)CC(=O)O)C
• InChI: InChI=1S/C29H41N7O12/c1-13(2)23(31-16(6)37)29(46)34-20(12-22(40)41)27(44)35-24(14(3)4)28(45)30-15(5)25(42)33-19(11-21(38)39)26(43)32-17-7-9-18(10-8-17)36(47)48/h7-10,13-15,19-20,23-24H,11-12H2,1-6H3,(H,30,45)(H,31,37)(H,32,43)(H,33,42)(H,34,46)(H,35,44)(H,38,39)(H,40,41)/t15-,19-,20-,23-,24-/m0/s1
• InChIKey: SIOKOOKURWWOID-PZQVQNRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-[(2S)-2-acetamido-3-methylbutanamido]propanoic acid
• IUPAC Traditional name: (3S)-3-{[(1S)-1-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-3-[(2S)-2-acetamido-3-methylbutanamido]propanoic acid
• Synonyms: Ac-Val-Asp-Val-Ala-Asp-PNA; Ac-VDVAD-PNA; Ac-Val-Asp-Val-Ala-Asp-paranitroanilide; Ac-Val-Asp-Gln-Gln-Asp-PNA; Ac-VDQQD-PNA; Ac-Val-Asp-Gln-Gln-Asp-paranitroanilide

Database IDs

• PubChem SID: 162105725
• PubChem CID: 25108784

CALCULATED PROPERTIES

• Acid pKa: 3.491639
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -4.205281
• LogD (pH = 7.4): -7.368206
• Log P: -1.040288
• Molar Refractivity: 164.7947 cm^3
• Polarizability: 63.25342 Å^3
• Polar Surface Area: 295.02 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA142

A colorimetric substrate for detection of Caspase-2 (ICH-1). Cleavage is monitored colorimetrically at ~405 nm.

REFERENCES

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Talanian, R.V., et al. 1997. J. Biol. Chem. 272, 9677.