(4S)-5-[(2S)-2-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}pyrrolidin-1-yl]-4-[(2S,3S)-2-acetamido-3-methylpentanamido]-5-oxopentanoic acid

• ChemBase ID: 106638
• Molecular Formular: C28H38N6O11
• Molecular Mass: 634.63492
• Monoisotopic Mass: 634.25985607
• SMILES: CC[C@H](C)[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N1CCC[C@H]1C(=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)N1CCC[C@H]1C(=O)N[C@H](C(=O)Nc1ccc(cc1)[N+](=O)[O-])CC(=O)O)CCC(=O)O)NC(=O)C)C
• InChI: InChI=1S/C28H38N6O11/c1-4-15(2)24(29-16(3)35)27(42)31-19(11-12-22(36)37)28(43)33-13-5-6-21(33)26(41)32-20(14-23(38)39)25(40)30-17-7-9-18(10-8-17)34(44)45/h7-10,15,19-21,24H,4-6,11-14H2,1-3H3,(H,29,35)(H,30,40)(H,31,42)(H,32,41)(H,36,37)(H,38,39)/t15-,19-,20-,21-,24-/m0/s1
• InChIKey: YXEIIOVAGGAMCZ-NYMCBPKFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-5-[(2S)-2-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}pyrrolidin-1-yl]-4-[(2S,3S)-2-acetamido-3-methylpentanamido]-5-oxopentanoic acid
• IUPAC Traditional name: (4S)-5-[(2S)-2-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}pyrrolidin-1-yl]-4-[(2S,3S)-2-acetamido-3-methylpentanamido]-5-oxopentanoic acid
• Synonyms: Ac-Ile-Glu-Pro-Asp-PNA; Ac-IEPD-PNA; Ac-Ile-Glu-Pro-Asp-paranitroanilide; N-Acetyl-Ile-Glu-Pro-Asp-p-nitroanilide

Database IDs

• MDL Number: MFCD02259221
• PubChem SID: 162087303
• PubChem CID: 2826717

CALCULATED PROPERTIES

• Molar Refractivity: 155.5468 cm^3
• Polarizability: 59.41278 Å^3
• Polar Surface Area: 257.13 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false
• Acid pKa: 3.498307
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -3.6769063
• LogD (pH = 7.4): -6.823064
• Log P: -0.38536876

PROPERTIES

Physical Property

• Solubility: DMSO: soluble
• 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 ... 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: ≥97% (HPLC)
• Shipped in: dry ice

DETAILS

MP Biomedicals - 03PNA153

A colorimetric substrate for Granzyme B (Kcat/Km = 66000 M^-1s^-1). Cleavage of pNA is monitored colorimetrically at ~405 nm (e = 9,160 M^-1cm^-1).

Sigma Aldrich - A6470

Amino Acid Sequence
NAc-Ile-Glu-Pro-Asp-pNA
Substrates
Chromogenic substrate for caspase 8 and granzyme B.

REFERENCES

• Harris, J.L. et al., J. Biol. Chem., 273:27364 (1998).
• Thornberry, N.A. et al., Science, 281:1312 (1998).