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Inhibitor Report for: Spirodiclofen

Spirodiclofen is an organochlorine acaricide, a dichlorobenzene, an oxaspiro compound and a gamma-lactone. It derives from a 1,3-dichlorobenzene CCE04 = T1JSJ6 (corrected with insertion). Overexpression of an alternative allele of carboxyl/choline esterase 4 (CCE04) of Tetranychus urticae is associated with high levels of resistance to the keto-enol acaricide spirodiclofen through sequestration. Hydrolysis of the ester bond gives the spirodiclofen enol which is the active compoud. Spirodiclofen is hydrolysed by CYP39E10 in mites. The ester bond is hydrolysed by esterases in plasma and liver of vertebrates. (Wei et al. 2019


General
Type Organochlorine, Acaricide
Chemical_Nomenclature [3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl] 2,2-dimethylbutanoate
Canonical SMILES CCC(C)(C)C(=O)OC1=C(C(=O)OC12CCCCC2)C3=C(C=C(C=C3)Cl)Cl
InChI InChI=1S/C21H24Cl2O4/c1-4-20(2,3)19(25)26-17-16(14-9-8-13(22)12-15(14)23)18(24)27-21(17)10-6-5-7-11-21/h8-9,12H,4-7,10-11H2,1-3H3
InChIKey DTDSAWVUFPGDMX-UHFFFAOYSA-N
Other name(s) UNII-3X7G31F5MX ; 3X7G31F5MX ; CHEBI:38639 ; ZINC2540062 ; SCHEMBL27234 ; CHEMBL2227839 ; Butanoic acid, 2,2-dimethyl-, 3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro(4.5)dec-3-en-4-yl ester
________________________________________________________________________________________________
MW|411.3
Formula|C21H24Cl2O4
CAS_number|148477-71-8
PubChem|177863
UniChem|DTDSAWVUFPGDMX-UHFFFAOYSA-N
IUPHAR|
Wikipedia|

Target
Families | Spirodiclofen ligand of proteins in family: Cholinesterase-like
Protein | tetur-t1jsj6

References:
Search PubMed for references concerning: Spirodiclofen
    Title: Overexpression of an alternative allele of carboxyl/choline esterase 4 (CCE04) of Tetranychus urticae is associated with high levels of resistance to the keto-enol acaricide spirodiclofen
    Wei P, Demaeght P, De Schutter K, Grigoraki L, Labropoulou V, Riga M, Vontas J, Nauen R, Dermauw W, Van Leeuwen T
    Ref: Pest Manag Sci, 76:1142, 2020 : PubMed

            

    Title: Transcriptome profiling of a spirodiclofen susceptible and resistant strain of the European red mite Panonychus ulmi using strand-specific RNA-seq
    Bajda S, Dermauw W, Greenhalgh R, Nauen R, Tirry L, Clark RM, Van Leeuwen T
    Ref: BMC Genomics, 16:974, 2015 : PubMed

            

    Title: Molecular analysis of resistance to acaricidal spirocyclic tetronic acids in Tetranychus urticae: CYP392E10 metabolizes spirodiclofen, but not its corresponding enol
    Demaeght P, Dermauw W, Tsakireli D, Khajehali J, Nauen R, Tirry L, Vontas J, Lummen P, Van Leeuwen T
    Ref: Insect Biochemistry & Molecular Biology, 43:544, 2013 : PubMed