(3S)-5-(2,6-difluorophenoxy)-3-[(2S)-3-methyl-2-(quinolin-2-ylformamido)butanamido]-4-oxopentanoic acid

• ChemBase ID: 106601
• Molecular Formular: C26H25F2N3O6
• Molecular Mass: 513.4900064
• Monoisotopic Mass: 513.17114198
• SMILES: CC(C)[C@H](NC(=O)c1ccc2c(n1)cccc2)C(=O)N[C@@H](CC(=O)O)C(=O)COc1c(F)cccc1F
• Canonical SMILES: OC(=O)C[C@@H](C(=O)COc1c(F)cccc1F)NC(=O)[C@H](C(C)C)NC(=O)c1ccc2c(n1)cccc2
• InChI: InChI=1S/C26H25F2N3O6/c1-14(2)23(31-25(35)19-11-10-15-6-3-4-9-18(15)29-19)26(36)30-20(12-22(33)34)21(32)13-37-24-16(27)7-5-8-17(24)28/h3-11,14,20,23H,12-13H2,1-2H3,(H,30,36)(H,31,35)(H,33,34)/t20-,23-/m0/s1
• InChIKey: OOBJCYKITXPCNS-REWPJTCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-5-(2,6-difluorophenoxy)-3-[(2S)-3-methyl-2-(quinolin-2-ylformamido)butanamido]-4-oxopentanoic acid
• IUPAC Traditional name: (3S)-5-(2,6-difluorophenoxy)-3-[(2S)-3-methyl-2-(quinolin-2-ylformamido)butanamido]-4-oxopentanoic acid
• Synonyms: Q-Val-Asp-OPH; Q-VD-OPH; Quinoline-Val-Asp-Difluorophenoxymethylketone

Database IDs

• PubChem SID: 162105544
• PubChem CID: 24794416

CALCULATED PROPERTIES

• Acid pKa: 3.8728373
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 1.8467753
• LogD (pH = 7.4): 0.2513318
• Log P: 3.4789119
• Molar Refractivity: 126.4353 cm^3
• Polarizability: 49.71118 Å^3
• Polar Surface Area: 134.69 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

MP Biomedicals - 03OPH109

An broad spectrum Caspase inhibitor for in vivo research. The novel Q-VD-OPH compound synthesized using proprietary technology is an irreversible caspase inhibitor specifically designed for in-vivo research.
The Q-VD-OPH irreversibily binds to activated Caspases to block apoptosis. Apoptosis is a physiological for of cell death, which plays important role in embryogenesis, cellular homoestasis, tissue atrophy , and removal damaged and mutated cells. Caspases, which acts as molecular chainsaw are the central components of apoptosis response. Caspases are Cysteine proteases that cleave after aspartate residue in their substrates. At least 7 of 14 known mammalian caspases have important role in apoptosis.
The OPH trap with its superior potency, proven cell permeability and minimal toxicity provides an exceptional alternative to the Fluoromethylketone family of inhibitors.
Caserta, T. M.; et al. Apoptosis, 2003, 8, 345-352.
Renolleau, S. et al. Journal of Neurochemistry, 2007, 100, 1062-1071.