SML0736

Dafadine A

≥98% (HPLC)

• Synonym(s): 4-[1-({ 5-[(2,6-Dimethylphenoxy)methyl]-3-isoxazolyl}carbonyl)-4-piperidinyl]pyridine
• Empirical Formula (Hill Notation): C₂₃H₂₅N₃O₃
• CAS Number: 1065506-69-5
• Molecular Weight: 391.46
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 15 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: N3(CCC(CC3)c4ccncc4)C(=O)c1n[o]c(c1)COc2c(cccc2C)C
• InChI: 1S/C23H25N3O3/c1-16-4-3-5-17(2)22(16)28-15-20-14-21(25-29-20)23(27)26-12-8-19(9-13-26)18-6-10-24-11-7-18/h3-7,10-11,14,19H,8-9,12-13,15H2,1-2H3
• InChI key: WNSNPYIHDMIFOO-UHFFFAOYSA-N

Description

Biochem/physiol Actions

Dafadine A is a selective inhibitor of C. elegans DAF-9 cytochrome P450, a key regulator of dauer formation, developmental timing and longevity. C. elegans has four life stages. In harsh environmental conditions, nematodes can convert to the L3 stage, known as the ""non-aging"" dauer stage, in which development ceases until improved conditions are sensed. Dafadine A can induce dauer formation and increased longevity in wild-type worms raised in nonstressful conditions. Dafadine A is the only inhibitor known to robustly inhibit DAF-9 in wild-type worms. It does not inhibit DAF-12 activity. Dafadine is active in mammalian systems, inhibiting CYP27A1, the mammalian functional ortholog of DAF-9 that oxidizes 4-cholesten-3-one to make 26-hydroxy-4-cholesten-3-one and Δ4-dafachronic acid, without inhibiting other sterol- and oxysterol-metabolizing P450s such as CYP7A1 or CYP7B1.

Dafadine A is a selective inhibitor of C. elegans DAF-9 cytochrome P450 and CYP7A1, the mammalian ortholog.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable