SML0736
Dafadine A
≥98% (HPLC)
Synonym(s):
4-[1-({ 5-[(2,6-Dimethylphenoxy)methyl]-3-isoxazolyl}carbonyl)-4-piperidinyl]pyridine
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About This Item
Empirical Formula (Hill Notation):
C23H25N3O3
CAS Number:
Molecular Weight:
391.46
UNSPSC Code:
12352200
NACRES:
NA.77
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
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 15 mg/mL, clear
storage temp.
2-8°C
Quality Level
Related Categories
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Guangxu Ma et al.
PLoS pathogens, 15(7), e1007960-e1007960 (2019-07-25)
Here, we discovered an endogenous dafachronic acid (DA) in the socioeconomically important parasitic nematode Haemonchus contortus. We demonstrate that DA promotes larval exsheathment and development in this nematode via a relatively conserved nuclear hormone receptor (DAF-12). This stimulatory effect is
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