(3S)-3-[(2S)-2-[(2S)-4-carbamoyl-2-[(2S)-2-acetamido-3-methylbutanamido]butanamido]-3-methylbutanamido]-3-[(4-nitrophenyl)carbamoyl]propanoic acid

• ChemBase ID: 106645
• Molecular Formular: C27H39N7O10
• Molecular Mass: 621.63946
• Monoisotopic Mass: 621.27584048
• SMILES: CC(C)[C@H](NC(=O)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N[C@@H](C(C)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](C(C)C)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)C)CCC(=O)N
• InChI: InChI=1S/C27H39N7O10/c1-13(2)22(29-15(5)35)26(41)31-18(10-11-20(28)36)24(39)33-23(14(3)4)27(42)32-19(12-21(37)38)25(40)30-16-6-8-17(9-7-16)34(43)44/h6-9,13-14,18-19,22-23H,10-12H2,1-5H3,(H2,28,36)(H,29,35)(H,30,40)(H,31,41)(H,32,42)(H,33,39)(H,37,38)/t18-,19-,22-,23-/m0/s1
• InChIKey: NMLZDQJCXWQHMU-ZZTDLJEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-[(2S)-2-[(2S)-4-carbamoyl-2-[(2S)-2-acetamido-3-methylbutanamido]butanamido]-3-methylbutanamido]-3-[(4-nitrophenyl)carbamoyl]propanoic acid
• IUPAC Traditional name: (3S)-3-[(2S)-2-[(2S)-4-carbamoyl-2-[(2S)-2-acetamido-3-methylbutanamido]butanamido]-3-methylbutanamido]-3-[(4-nitrophenyl)carbamoyl]propanoic acid
• Synonyms: Ac-Val-Gln-Val-Asp-PNA; Ac-VQVD-PNA; Ac-Val-Gln-Val-Asp-paranitroanilide

Database IDs

• PubChem SID: 162105562
• PubChem CID: 25108795

CALCULATED PROPERTIES

• LogD (pH = 5.5): -2.8159134
• LogD (pH = 7.4): -4.3254843
• Log P: -1.0220504
• Molar Refractivity: 154.0745 cm^3
• Polarizability: 58.944584 Å^3
• Polar Surface Area: 271.71 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false
• Acid pKa: 3.7051303
• H Acceptors: 10
• H Donor: 7

DETAILS

MP Biomedicals - 03PNA162

A colorimetric substrate for Caspase-3.

REFERENCES

• Talanian, R. et al., J. Biol. Chem., 272:9677 (1997).