(4S)-4-{[(1S,2S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-4-[(2S)-2-acetamido-3-methylbutanamido]butanoic acid

• ChemBase ID: 106633
• Molecular Formular: C28H40N6O11
• Molecular Mass: 636.6508
• Monoisotopic Mass: 636.27550613
• SMILES: CC[C@H](C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](NC(=O)C)C(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N[C@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])CC(=O)O)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)C)CCC(=O)O)C
• InChI: InChI=1S/C28H40N6O11/c1-6-15(4)24(33-25(40)19(11-12-21(36)37)31-27(42)23(14(2)3)29-16(5)35)28(43)32-20(13-22(38)39)26(41)30-17-7-9-18(10-8-17)34(44)45/h7-10,14-15,19-20,23-24H,6,11-13H2,1-5H3,(H,29,35)(H,30,41)(H,31,42)(H,32,43)(H,33,40)(H,36,37)(H,38,39)/t15-,19-,20-,23-,24-/m0/s1
• InChIKey: VXTVKOWKXXPPNE-PZQVQNRFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S,2S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-4-[(2S)-2-acetamido-3-methylbutanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S,2S)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-methylbutyl]carbamoyl}-4-[(2S)-2-acetamido-3-methylbutanamido]butanoic acid
• Synonyms: Ac-Val-Glu-Ile-Asp-PNA; Ac-VEID-PNA; Ac-Val-Glu-Ile-Asp-paranitroanilide; N-Acetyl-Val-Glu-Ile-Asp-p-nitroanilide

Database IDs

• MDL Number: MFCD01318842
• PubChem SID: 162087215
• PubChem CID: 25108783

CALCULATED PROPERTIES

• Acid pKa: 3.6222174
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -2.8518548
• LogD (pH = 7.4): -6.1014934
• Log P: 0.22946088
• Molar Refractivity: 156.8533 cm^3
• Polarizability: 60.115948 Å^3
• Polar Surface Area: 265.92 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble2 mM
• Apperance: 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 ... CASP6(839)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 03PNA141

A colorimetric substrate for caspase-6 (Mch2). Cleavage is monitored colorimetrically at ~405 nm.

Sigma Aldrich - A5220

Amino Acid Sequence
NAc-Val-Glu-Ile-Asp-pNA
Substrates
Colormetric substrate for caspase 6.

REFERENCES

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