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Substrate Report for: DEUP

Diethylumbelliferyl phosphate is a selective, potent cholesterol esterase inhibitor. It blocks steroidogenesis primarily by preventing cholesterol transport into the mitochondria of steroidogenic cells. Inhibitors of cholesterol esterase are anticipated to limit the absorption of dietary cholesterol. IC50 = 11.6 microM. Substrate for testing OP-hydrolase activity (in particular the modified carboxylesterase E3 from Lucilia cuprina).


General
Type Organophosphate, Coumarin
Chemical_Nomenclature diethyl (2-oxochromen-7-yl) phosphate
Canonical SMILES CCOP(=O)(OCC)OC1=CC2=C(C=C1)C=CC(=O)O2
InChI InChI=1S/C13H15O6P/c1-3-16-20(15,17-4-2)19-11-7-5-10-6-8-13(14)18-12(10)9-11/h5-9H,3-4H2,1-2H3
InChIKey LZXQXHKDCNQUOF-UHFFFAOYSA-N
Other name(s) diethyl 7-hydroxycoumaryl phosphate ; O,O-diethyl O-(2-oxo-2H-chromen-7-yl) phosphate ; CHEMBL1719220 ; dECP ; DEUP ; UBP ; D7692_SIGMA ; SCHEMBL404341 ; Diethylumbelliferyl phosphate
________________________________________________________________________________________________
MW|298.23
Formula|C13H15O6P
CAS_number|897-83-6
PubChem|16219277
UniChem|LZXQXHKDCNQUOF-UHFFFAOYSA-N
IUPHAR|
Wikipedia|

Target
Families | DEUP ligand of proteins in family: Carb_B_Arthropoda, Hormone-sensitive_lipase_like, Arylacetamide_deacetylase
Protein | human-NCEH1

References:
Search PubMed for references concerning: DEUP

2 more
    Title: Conformational Disorganization within the Active Site of a Recently Evolved Organophosphate Hydrolase Limits Its Catalytic Efficiency
    Mabbitt PD, Correy GJ, Meirelles T, Fraser NJ, Coote ML, Jackson CJ
    Ref: Biochemistry, 55:1408, 2016 : PubMed

            

    Title: Hydrolysis of organophosphorus insecticides by in vitro modified carboxylesterase E3 from Lucilia cuprina
    Heidari R, Devonshire AL, Campbell BE, Bell KL, Dorrian SJ, Oakeshott JG, Russell RJ
    Ref: Insect Biochemistry & Molecular Biology, 34:353, 2004 : PubMed

            

    Title: Kinetic efficiency of mutant carboxylesterases implicated in organophosphate insecticide resistance
    Devonshire AL, Heidari R, Bell KL, Campbell PM, Campbell BE, Odgers WA, Oakeshott JG, Russell RJ
    Ref: Pesticide Biochemistry and Physiology, 76:1, 2003 : PubMed