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, Chromen
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
Target
Structures : No structure
Families : Carb_B_Arthropoda, Hormone-sensitive_lipase_like, Arylacetamide_deacetylase
References (18)
| Title : Conformational Disorganization within the Active Site of a Recently Evolved Organophosphate Hydrolase Limits Its Catalytic Efficiency - Mabbitt_2016_Biochemistry_55_1408 |
| Author(s) : Mabbitt PD , Correy GJ , Meirelles T , Fraser NJ , Coote ML , Jackson CJ |
| Ref : Biochemistry , 55 :1408 , 2016 |
| Abstract : |
| PubMedSearch : Mabbitt_2016_Biochemistry_55_1408 |
| PubMedID: 26881849 |
| Gene_locus related to this paper: luccu-E3aest7 |
| Title : Conformational Disorganization within the Active Site of a Recently Evolved Organophosphate Hydrolase Limits Its Catalytic Efficiency - Mabbitt_2016_Biochemistry_55_1408 |
| Author(s) : Mabbitt PD , Correy GJ , Meirelles T , Fraser NJ , Coote ML , Jackson CJ |
| Ref : Biochemistry , 55 :1408 , 2016 |
| Abstract : |
| PubMedSearch : Mabbitt_2016_Biochemistry_55_1408 |
| PubMedID: 26881849 |
| Gene_locus related to this paper: luccu-E3aest7 |
| Title : Conformational Disorganization within the Active Site of a Recently Evolved Organophosphate Hydrolase Limits Its Catalytic Efficiency - Mabbitt_2016_Biochemistry_55_1408 |
| Author(s) : Mabbitt PD , Correy GJ , Meirelles T , Fraser NJ , Coote ML , Jackson CJ |
| Ref : Biochemistry , 55 :1408 , 2016 |
| Abstract : |
| PubMedSearch : Mabbitt_2016_Biochemistry_55_1408 |
| PubMedID: 26881849 |
| Gene_locus related to this paper: luccu-E3aest7 |
| Title : Organophosphate and pyrethroid hydrolase activities of mutant Esterases from the cotton bollworm Helicoverpa armigera - Li_2013_PLoS.One_8_e77685 |
| Author(s) : Li Y , Farnsworth CA , Coppin CW , Teese MG , Liu JW , Scott C , Zhang X , Russell RJ , Oakeshott JG |
| Ref : PLoS ONE , 8 :e77685 , 2013 |
| Abstract : |
| PubMedSearch : Li_2013_PLoS.One_8_e77685 |
| PubMedID: 24204917 |
| Gene_locus related to this paper: helam-d5g3c9 , helam-d5g3d2 , helam-d5g3d3 , helam-d5g3d4 , helam-d5g3d5 , helam-d5kx87 , helam-d5kx99 , helam-d5kxa9 , helam-d9iv61 , helam-d9iv62 , helam-h9zvh4 , helam-s4wfz6 |
| Title : Organophosphate and pyrethroid hydrolase activities of mutant Esterases from the cotton bollworm Helicoverpa armigera - Li_2013_PLoS.One_8_e77685 |
| Author(s) : Li Y , Farnsworth CA , Coppin CW , Teese MG , Liu JW , Scott C , Zhang X , Russell RJ , Oakeshott JG |
| Ref : PLoS ONE , 8 :e77685 , 2013 |
| Abstract : |
| PubMedSearch : Li_2013_PLoS.One_8_e77685 |
| PubMedID: 24204917 |
| Gene_locus related to this paper: helam-d5g3c9 , helam-d5g3d2 , helam-d5g3d3 , helam-d5g3d4 , helam-d5g3d5 , helam-d5kx87 , helam-d5kx99 , helam-d5kxa9 , helam-d9iv61 , helam-d9iv62 , helam-h9zvh4 , helam-s4wfz6 |
| Title : Organophosphate and pyrethroid hydrolase activities of mutant Esterases from the cotton bollworm Helicoverpa armigera - Li_2013_PLoS.One_8_e77685 |
| Author(s) : Li Y , Farnsworth CA , Coppin CW , Teese MG , Liu JW , Scott C , Zhang X , Russell RJ , Oakeshott JG |
| Ref : PLoS ONE , 8 :e77685 , 2013 |
| Abstract : |
| PubMedSearch : Li_2013_PLoS.One_8_e77685 |
| PubMedID: 24204917 |
| Gene_locus related to this paper: helam-d5g3c9 , helam-d5g3d2 , helam-d5g3d3 , helam-d5g3d4 , helam-d5g3d5 , helam-d5kx87 , helam-d5kx99 , helam-d5kxa9 , helam-d9iv61 , helam-d9iv62 , helam-h9zvh4 , helam-s4wfz6 |
| Title : Hydrolysis of organophosphorus insecticides by in vitro modified carboxylesterase E3 from Lucilia cuprina - Heidari_2004_Insect.Biochem.Mol.Biol_34_353 |
| Author(s) : Heidari R , Devonshire AL , Campbell BE , Bell KL , Dorrian SJ , Oakeshott JG , Russell RJ |
| Ref : Insect Biochemistry & Molecular Biology , 34 :353 , 2004 |
| Abstract : |
| PubMedSearch : Heidari_2004_Insect.Biochem.Mol.Biol_34_353 |
| PubMedID: 15041019 |
| Gene_locus related to this paper: luccu-E3aest7 |
| Title : Hydrolysis of organophosphorus insecticides by in vitro modified carboxylesterase E3 from Lucilia cuprina - Heidari_2004_Insect.Biochem.Mol.Biol_34_353 |
| Author(s) : Heidari R , Devonshire AL , Campbell BE , Bell KL , Dorrian SJ , Oakeshott JG , Russell RJ |
| Ref : Insect Biochemistry & Molecular Biology , 34 :353 , 2004 |
| Abstract : |
| PubMedSearch : Heidari_2004_Insect.Biochem.Mol.Biol_34_353 |
| PubMedID: 15041019 |
| Gene_locus related to this paper: luccu-E3aest7 |
| Title : Hydrolysis of organophosphorus insecticides by in vitro modified carboxylesterase E3 from Lucilia cuprina - Heidari_2004_Insect.Biochem.Mol.Biol_34_353 |
| Author(s) : Heidari R , Devonshire AL , Campbell BE , Bell KL , Dorrian SJ , Oakeshott JG , Russell RJ |
| Ref : Insect Biochemistry & Molecular Biology , 34 :353 , 2004 |
| Abstract : |
| PubMedSearch : Heidari_2004_Insect.Biochem.Mol.Biol_34_353 |
| PubMedID: 15041019 |
| Gene_locus related to this paper: luccu-E3aest7 |
| Title : Kinetic efficiency of mutant carboxylesterases implicated in organophosphate insecticide resistance - Devonshire_2003_Pestic.Biochem.Physiol_76_1 |
| Author(s) : Devonshire AL , Heidari R , Bell KL , Campbell PM , Campbell BE , Odgers WA , Oakeshott JG , Russell RJ |
| Ref : Pesticide Biochemistry and Physiology , 76 :1 , 2003 |
| Abstract : |
| PubMedSearch : Devonshire_2003_Pestic.Biochem.Physiol_76_1 |
| PubMedID: |
| Gene_locus related to this paper: luccu-E3aest7 , musdo-EST23aes07 |
| Title : Kinetic efficiency of mutant carboxylesterases implicated in organophosphate insecticide resistance - Devonshire_2003_Pestic.Biochem.Physiol_76_1 |
| Author(s) : Devonshire AL , Heidari R , Bell KL , Campbell PM , Campbell BE , Odgers WA , Oakeshott JG , Russell RJ |
| Ref : Pesticide Biochemistry and Physiology , 76 :1 , 2003 |
| Abstract : |
| PubMedSearch : Devonshire_2003_Pestic.Biochem.Physiol_76_1 |
| PubMedID: |
| Gene_locus related to this paper: luccu-E3aest7 , musdo-EST23aes07 |
| Title : Kinetic efficiency of mutant carboxylesterases implicated in organophosphate insecticide resistance - Devonshire_2003_Pestic.Biochem.Physiol_76_1 |
| Author(s) : Devonshire AL , Heidari R , Bell KL , Campbell PM , Campbell BE , Odgers WA , Oakeshott JG , Russell RJ |
| Ref : Pesticide Biochemistry and Physiology , 76 :1 , 2003 |
| Abstract : |
| PubMedSearch : Devonshire_2003_Pestic.Biochem.Physiol_76_1 |
| PubMedID: |
| Gene_locus related to this paper: luccu-E3aest7 , musdo-EST23aes07 |
| Title : Diethylumbelliferyl phosphate inhibits steroidogenesis by interfering with a long-lived factor acting between protein kinase A activation and induction of the steroidogenic acute regulatory protein (StAR) - Choi_1995_Eur.J.Biochem_234_680 |
| Author(s) : Choi YS , Stocco DM , Freeman DA |
| Ref : European Journal of Biochemistry , 234 :680 , 1995 |
| Abstract : |
| PubMedSearch : Choi_1995_Eur.J.Biochem_234_680 |
| PubMedID: 8536719 |
| Title : Diethylumbelliferyl phosphate inhibits steroidogenesis by interfering with a long-lived factor acting between protein kinase A activation and induction of the steroidogenic acute regulatory protein (StAR) - Choi_1995_Eur.J.Biochem_234_680 |
| Author(s) : Choi YS , Stocco DM , Freeman DA |
| Ref : European Journal of Biochemistry , 234 :680 , 1995 |
| Abstract : |
| PubMedSearch : Choi_1995_Eur.J.Biochem_234_680 |
| PubMedID: 8536719 |
| Title : Diethylumbelliferyl phosphate inhibits steroidogenesis by interfering with a long-lived factor acting between protein kinase A activation and induction of the steroidogenic acute regulatory protein (StAR) - Choi_1995_Eur.J.Biochem_234_680 |
| Author(s) : Choi YS , Stocco DM , Freeman DA |
| Ref : European Journal of Biochemistry , 234 :680 , 1995 |
| Abstract : |
| PubMedSearch : Choi_1995_Eur.J.Biochem_234_680 |
| PubMedID: 8536719 |
| Title : Evidence that a neutral cholesteryl ester hydrolase is responsible for the extralysosomal hydrolysis of high-density lipoprotein cholesteryl ester in rat hepatoma cells (Fu5AH) - Delamatre_1993_J.Cell.Physiol_157_164 |
| Author(s) : Delamatre JG , Carter RM , Hornick CA |
| Ref : Journal of Cellular Physiology , 157 :164 , 1993 |
| Abstract : |
| PubMedSearch : Delamatre_1993_J.Cell.Physiol_157_164 |
| PubMedID: 8408234 |
| Title : Evidence that a neutral cholesteryl ester hydrolase is responsible for the extralysosomal hydrolysis of high-density lipoprotein cholesteryl ester in rat hepatoma cells (Fu5AH) - Delamatre_1993_J.Cell.Physiol_157_164 |
| Author(s) : Delamatre JG , Carter RM , Hornick CA |
| Ref : Journal of Cellular Physiology , 157 :164 , 1993 |
| Abstract : |
| PubMedSearch : Delamatre_1993_J.Cell.Physiol_157_164 |
| PubMedID: 8408234 |
| Title : Evidence that a neutral cholesteryl ester hydrolase is responsible for the extralysosomal hydrolysis of high-density lipoprotein cholesteryl ester in rat hepatoma cells (Fu5AH) - Delamatre_1993_J.Cell.Physiol_157_164 |
| Author(s) : Delamatre JG , Carter RM , Hornick CA |
| Ref : Journal of Cellular Physiology , 157 :164 , 1993 |
| Abstract : |
| PubMedSearch : Delamatre_1993_J.Cell.Physiol_157_164 |
| PubMedID: 8408234 |