923556-77-8

Basic information

• Product Name: N-(2,4-dimethoxyphenyl)-2-propylpentanamide
• Synonyms: N-(2,4-dimethoxyphenyl)-2-propylpentanamide
• CAS NO: 923556-77-8
• Molecular Formula: C16H25NO3
• Molecular Weight: 279.3746
• Mol File: 923556-77-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(2,4-dimethoxyphenyl)-2-propylpentanamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,4-dimethoxyphenyl)-2-propylpentanamide(923556-77-8)
• EPA Substance Registry System: N-(2,4-dimethoxyphenyl)-2-propylpentanamide(923556-77-8)

Safety Data

• Hazardous Substances Data: 923556-77-8(Hazardous Substances Data)

Upstream product

• 99-66-1 valproic acid 
• 38064-90-3 2,4-dimethoxytoluene 

Relevant articles and documents

Exploring the biotransformation of N-(2-hydroxyphenyl)-2-propylpentanamide (an aryl valproic acid derivative) by CYP2C11, using in silico predictions and in vitro studies

Objectives: N-(2-hydroxyphenyl)-2-propylpentanamide (HO-AAVPA), a derivative of valproic acid (VPA), has been proposed as a potential anticancer agent due to its improved antiproliferative effects in some cancer cell lines. Although there is evidence that VPA is metabolized by cytochrome P450 2C11 rat isoform, HO-AAVPA CYP-mediated metabolism has not yet been fully explored. Therefore, in this work, the biotransformation of HO-AAVPA by CYP2C11 was investigated. Methods: Kinetic parameters and spectral interaction between HO-AAVPA and CYP were evaluated using rat liver microsomes. The participation of CYP2C11 in metabolism of HO-AAVPA was confirmed by cimetidine (CIM) inhibition assay. Docking and molecular dynamics simulations coupled to MMGBSA methods were used in theoretical study. Key findings: HO-AAVPA is metabolized by CYP enzymes (KM?=?38.94?μm), yielding a hydroxylated metabolite according to its HPLC retention time (5.4?min) and MS analysis (252.2?m/z). In addition, CIM inhibition in rat liver microsomes (Ki?=?59.23?μm) confirmed that CYP2C11 is mainly involved in HO-AAVPA metabolism. Furthermore, HO-AAVPA interacts with CYP2C11 as a type I ligand. HO-AAVPA is stabilized at the CYP2C11 ligand recognition site through a map of interactions similar to other typical CYP2C11 substrates. Conclusion: Therefore, rat liver CYP2C11 isoform is able to metabolize HO-AAVPA.