(4S)-4-{[(1S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(2S)-3-carboxy-2-acetamidopropanamido]butanoic acid

• ChemBase ID: 106630
• Molecular Formular: C26H34N6O13
• Molecular Mass: 638.58056
• Monoisotopic Mass: 638.21838518
• SMILES: CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(=O)O)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)CC(=O)O)CCC(=O)O
• InChI: InChI=1S/C26H34N6O13/c1-12(2)22(26(43)30-18(11-21(38)39)24(41)28-14-4-6-15(7-5-14)32(44)45)31-23(40)16(8-9-19(34)35)29-25(42)17(10-20(36)37)27-13(3)33/h4-7,12,16-18,22H,8-11H2,1-3H3,(H,27,33)(H,28,41)(H,29,42)(H,30,43)(H,31,40)(H,34,35)(H,36,37)(H,38,39)/t16-,17-,18-,22-/m0/s1
• InChIKey: GGXRLUDNGFFUKI-ORGXJRBJSA-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)-3-carboxy-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)-3-carboxy-2-acetamidopropanamido]butanoic acid
• Synonyms: Ac-Asp-Glu-Val-Asp-PNA; Ac-D-E-V-D-PNA; Ac-Asp-Glu-Val-Asp-paranitroanilide; Ac-DEVD-pNA; N-Acetyl-Asp-Glu-Val-Asp p-nitroanilide

Database IDs

• CAS Number: 189950-66-1
• MDL Number: MFCD00792707
• PubChem SID: 24890668; 162087214
• PubChem CID: 11527474

CALCULATED PROPERTIES

• Acid pKa: 3.3524659
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -6.6413436
• LogD (pH = 7.4): -11.389325
• Log P: -1.7444149
• Molar Refractivity: 149.2921 cm^3
• Polarizability: 57.173653 Å^3
• Polar Surface Area: 303.22 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CASP3(836)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 03PNA138

A colorimetric substrate for caspase-3 (Km = 9.7 μM), CCP-32 and related cysteine proteases. Sequence is based on the P1-P4 tetrapeptide cleavage site of poly(ADP-ribose) polymerase (PARP) and includes Asp216. Caspase-3 is the protease responsible for the cleavage of PARP. Also a substrate for caspase-6, caspase-7, caspase-8, and caspase-10. Cleavage of pNA is monitored colorimetrically at ~405 nm.

Sigma Aldrich - A2559

Amino Acid Sequence
NAc-Asp-Glu-Val-Asp-pNA
Biochem/physiol Actions
Colorimetric substrate for caspase 3, a protease that is rapidly activated when cells are exposed to apoptotic conditions and that cleaves poly(ADP-ribose) polymerase.

REFERENCES

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Nicholson, D.W. et al., Nature, 376:37 (1995).
• Cardone, M.H., et al. 1998. Science 282, 1318.
• Lazebnik, Y.A., et al. 1994. Nature 371, 346.