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

• ChemBase ID: 106632
• Molecular Formular: C27H38N6O12
• Molecular Mass: 638.62362
• Monoisotopic Mass: 638.25477069
• SMILES: CC[C@H](C)[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H]([C@@H](C)O)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)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])CC(=O)O)[C@H](O)C)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C27H38N6O12/c1-5-13(2)22(28-15(4)35)26(42)30-18(10-11-20(36)37)24(40)32-23(14(3)34)27(43)31-19(12-21(38)39)25(41)29-16-6-8-17(9-7-16)33(44)45/h6-9,13-14,18-19,22-23,34H,5,10-12H2,1-4H3,(H,28,35)(H,29,41)(H,30,42)(H,31,43)(H,32,40)(H,36,37)(H,38,39)/t13-,14+,18-,19-,22-,23-/m0/s1
• InChIKey: FHURKTIGZAIQGR-BQCLNCLCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-4-[(2S,3S)-2-acetamido-3-methylpentanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S,2R)-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}-2-hydroxypropyl]carbamoyl}-4-[(2S,3S)-2-acetamido-3-methylpentanamido]butanoic acid
• Synonyms: Ac-Ile-Glu-Thr-Asp-PNA; Ac-I-E-T-D-PNA; Ac-Ile-Glu-Thr-Asp-paranitroanilide; Ac-IETD-pNA; N-Acetyl-Ile-Glu-Thr-Asp-p-nitroanilide

Database IDs

• MDL Number: MFCD01318840
• PubChem SID: 162105598
• PubChem CID: 25108782

CALCULATED PROPERTIES

• Acid pKa: 3.4586117
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -4.6570654
• LogD (pH = 7.4): -7.7651324
• Log P: -1.2883693
• Molar Refractivity: 153.8202 cm^3
• Polarizability: 58.987675 Å^3
• Polar Surface Area: 286.15 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

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 ... CARD8(22900), CASP8(841), CASP8AP2(9994), CFLAR(8837), GZMB(3002)mouse ... CFLAR(117279), GZMB(171528)rat ... CASP8(12370), CFLAR(12633), GZMB(14939), RGD1561819(502004), RGD1562700(502007)

Product Information

• Purity: ≥95%
• Empirical Formula (Hill Notation): C27H38N6O12

DETAILS

MP Biomedicals - 03PNA140

A colorimetric substrate for the detection of caspase-8 and granzyme B activity.

Sigma Aldrich - A9968

Amino Acid Sequence
NAc-Ile-Glu-Thr-Asp-pNA
Application
Chromogenic substrate for caspase 8 and granzyme B.
Biochem/physiol Actions
IETD is the sequence of amino acid residues 172-175 of procaspase 3, which is cleaved during apoptosis to produce the p12 subunit and a p20 peptide that is further cleaved to form the p17 subunit of mature caspase 3.

REFERENCES

• Thornberry, N.A. et al., Science, 281:1312 (1998).
• Talanian, R.V. et al., J. Biol. Chem., 272:9677 (1997).
• Koeplinger, K.A., et al. 2000. Protein Exp. Purif. 18, 378.