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

• ChemBase ID: 106643
• Molecular Formular: C28H38N6O13
• Molecular Mass: 666.63372
• Monoisotopic Mass: 666.24968531
• SMILES: CC(C)C[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: OC(=O)CC[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](NC(=O)C)CC(C)C)CCC(=O)O
• InChI: InChI=1S/C28H38N6O13/c1-14(2)12-20(29-15(3)35)28(45)32-18(8-10-22(36)37)25(42)31-19(9-11-23(38)39)26(43)33-21(13-24(40)41)27(44)30-16-4-6-17(7-5-16)34(46)47/h4-7,14,18-21H,8-13H2,1-3H3,(H,29,35)(H,30,44)(H,31,42)(H,32,45)(H,33,43)(H,36,37)(H,38,39)(H,40,41)/t18-,19-,20-,21-/m0/s1
• InChIKey: JQHHXVRISZLHFQ-TUFLPTIASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-{[(1S)-3-carboxy-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}propyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• IUPAC Traditional name: (4S)-4-{[(1S)-3-carboxy-1-{[(1S)-2-carboxy-1-[(4-nitrophenyl)carbamoyl]ethyl]carbamoyl}propyl]carbamoyl}-4-[(2S)-2-acetamido-4-methylpentanamido]butanoic acid
• Synonyms: Ac-Leu-Glu-Glu-Asp-PNA; Ac-LEED-PNA; Ac-Leu-Glu-Glu-Asp-paranitroanilide

Database IDs

• PubChem SID: 162105560
• PubChem CID: 25108792

CALCULATED PROPERTIES

• Acid pKa: 3.2415442
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -6.2140036
• LogD (pH = 7.4): -10.834873
• Log P: -1.0891387
• Molar Refractivity: 158.7251 cm^3
• Polarizability: 60.797123 Å^3
• Polar Surface Area: 303.22 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA158

A colorimetric substrate for Caspase-13.

REFERENCES

• Humke, E.W. et al., J. Biol. Chem., 273(25):15702 (1998).