(3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-(1H-indol-3-yl)propanamido]-3-methylbutanamido]propanamido]-3-[(4-nitrophenyl)carbamoyl]propanoic acid

• ChemBase ID: 106650
• Molecular Formular: C31H37N7O9
• Molecular Mass: 651.66698
• Monoisotopic Mass: 651.2652758
• SMILES: CC(C)[C@H](NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)C)C(=O)N[C@@H](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](NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)C)C
• InChI: InChI=1S/C31H37N7O9/c1-16(2)27(37-30(44)24(34-18(4)39)13-19-15-32-23-8-6-5-7-22(19)23)31(45)33-17(3)28(42)36-25(14-26(40)41)29(43)35-20-9-11-21(12-10-20)38(46)47/h5-12,15-17,24-25,27,32H,13-14H2,1-4H3,(H,33,45)(H,34,39)(H,35,43)(H,36,42)(H,37,44)(H,40,41)/t17-,24-,25-,27-/m0/s1
• InChIKey: HSKHBBWGMHIMEG-KTIISADKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-(1H-indol-3-yl)propanamido]-3-methylbutanamido]propanamido]-3-[(4-nitrophenyl)carbamoyl]propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-2-[(2S)-2-acetamido-3-(1H-indol-3-yl)propanamido]-3-methylbutanamido]propanamido]-3-[(4-nitrophenyl)carbamoyl]propanoic acid
• Synonyms: Ac-Trp-Val-Ala-Asp-PNA; Ac-WVAD-PNA; Ac-Trp-Val-Ala-Asp-paranitroanilide

Database IDs

• PubChem SID: 162106021
• PubChem CID: 25108797

CALCULATED PROPERTIES

• Acid pKa: 3.5678487
• H Acceptors: 9
• H Donor: 7
• LogD (pH = 5.5): -0.92072326
• LogD (pH = 7.4): -2.3483813
• Log P: 1.0056361
• Molar Refractivity: 168.1718 cm^3
• Polarizability: 64.96359 Å^3
• Polar Surface Area: 244.41 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03PNA167

A colorimetric substrate for Caspase-1.