Trichloropropene-oxide

A potent epoxide hydrase and aryl hydrocarbon hydroxylase inhibitor. It enhances the tumor-initiating ability of certain carcinogens.

General

Type : Epoxide

Chemical_Nomenclature : 2-(trichloromethyl)oxirane

Canonical SMILES : C1C(O1)C(Cl)(Cl)Cl

InChI : InChI=1S\/C3H3Cl3O\/c4-3(5,6)2-1-7-2\/h2H,1H2

InChIKey : VFEXYZINKMLLAK-UHFFFAOYSA-N

Other name(s) : 2-(Trichloromethyl)oxirane,Trichloropropene oxide,TCPO,SCHEMBL2550267,1,2-Epoxy-3,3,3-trichloropropane,(Trichloromethyl)oxirane


MW : 161.41

Formula : C3H3Cl3O

CAS_number : 3083-23-6

PubChem : 18321

UniChem : VFEXYZINKMLLAK-UHFFFAOYSA-N

IUPHAR :

Wikipedia :

Target

Families : Trichloropropene-oxide ligand of proteins in family: Epoxide_hydrolase

Stucture :

Protein : human-EPHX1

References (12)

Title : Oviductal microsomal epoxide hydrolase (EPHX1) reduces reactive oxygen species (ROS) level and enhances preimplantation mouse embryo development - Cheong_2009_Biol.Reprod_81_126
Author(s) : Cheong AW , Lee YL , Liu WM , Yeung WS , Lee KF
Ref : Biol Reprod , 81 :126 , 2009
Abstract : Cheong_2009_Biol.Reprod_81_126
ESTHER : Cheong_2009_Biol.Reprod_81_126
PubMedSearch : Cheong_2009_Biol.Reprod_81_126
PubMedID: 19321813

Title : Phenytoin embryopathy: effect of epoxide hydrolase inhibitor on phenytoin exposure in utero in C57BL\/6J mice - Hartsfield_1995_Biochem.Mol.Med_56_131
Author(s) : Hartsfield JK, Jr. , Holmes LB , Morel JG
Ref : Biochemical & Molecular Medicine , 56 :131 , 1995
Abstract : Hartsfield_1995_Biochem.Mol.Med_56_131
ESTHER : Hartsfield_1995_Biochem.Mol.Med_56_131
PubMedSearch : Hartsfield_1995_Biochem.Mol.Med_56_131
PubMedID: 8825076

Title : An investigation of the formation of cytotoxic, genotoxic, protein-reactive and stable metabolites from naphthalene by human liver microsomes - Tingle_1993_Biochem.Pharmacol_46_1529
Author(s) : Tingle MD , Pirmohamed M , Templeton E , Wilson AS , Madden S , Kitteringham NR , Park BK
Ref : Biochemical Pharmacology , 46 :1529 , 1993
Abstract : Tingle_1993_Biochem.Pharmacol_46_1529
ESTHER : Tingle_1993_Biochem.Pharmacol_46_1529
PubMedSearch : Tingle_1993_Biochem.Pharmacol_46_1529
PubMedID: 8240407

Title : Human liver cytosolic epoxide hydrolases - Schladt_1988_Eur.J.Biochem_176_715
Author(s) : Schladt L , Thomas H , Hartmann R , Oesch F
Ref : European Journal of Biochemistry , 176 :715 , 1988
Abstract : Schladt_1988_Eur.J.Biochem_176_715
ESTHER : Schladt_1988_Eur.J.Biochem_176_715
PubMedSearch : Schladt_1988_Eur.J.Biochem_176_715
PubMedID: 3169021

Title : Purification of microsomal epoxide hydrolase from liver of rhesus monkey: partial separation of cis- and trans-stilbene oxide hydrolase - Moody_1987_Arch.Biochem.Biophys_258_156
Author(s) : Moody DE , Hammock BD
Ref : Archives of Biochemistry & Biophysics , 258 :156 , 1987
Abstract : Moody_1987_Arch.Biochem.Biophys_258_156
ESTHER : Moody_1987_Arch.Biochem.Biophys_258_156
PubMedSearch : Moody_1987_Arch.Biochem.Biophys_258_156
PubMedID: 3310896

Title : Selective inhibition and selective induction of multiple microsomal epoxide hydrolases - Guenthner_1986_Biochem.Pharmacol_35_839
Author(s) : Guenthner TM
Ref : Biochemical Pharmacology , 35 :839 , 1986
Abstract : Guenthner_1986_Biochem.Pharmacol_35_839
ESTHER : Guenthner_1986_Biochem.Pharmacol_35_839
PubMedSearch : Guenthner_1986_Biochem.Pharmacol_35_839
PubMedID: 3954789

Title : Nuclear metabolism. II. Further studies on epoxide hydrolase activity - Gazzotti_1981_Chem.Biol.Interact_35_311
Author(s) : Gazzotti G , Garattini E , Salmona M
Ref : Chemico-Biological Interactions , 35 :311 , 1981
Abstract : Gazzotti_1981_Chem.Biol.Interact_35_311
ESTHER : Gazzotti_1981_Chem.Biol.Interact_35_311
PubMedSearch : Gazzotti_1981_Chem.Biol.Interact_35_311
PubMedID: 7226277

Title : Inhibition of mono-oxygenase activities by 1,1,1-trichloropropene 2,3-oxide, an inhibitor of epoxide hydrase, in rat liver microsomes -
Author(s) : Shimada T , Sato R
Ref : Biochemical Pharmacology , 28 :1777 , 1979
PubMedID: 475837

Title : Effects of the epoxide hydrase inhibitor, 1,1,1-trichloropropane-2,3-oxide on the genetic activity of aflatoxin B1 metabolites in in vitro activation test systems - Callen_1978_Mutat.Res_49_371
Author(s) : Callen DF , Ong TM
Ref : Mutat Res , 49 :371 , 1978
Abstract : Callen_1978_Mutat.Res_49_371
ESTHER : Callen_1978_Mutat.Res_49_371
PubMedSearch : Callen_1978_Mutat.Res_49_371
PubMedID: 147417

Title : Benzo(a)pyrene metabolism in mouse epidermis. Analysis by high pressure liquid chromatography and DNA binding - Berry_1977_Chem.Biol.Interact_18_129
Author(s) : Berry DL , Bracken WR , Slaga TJ , Wilson NM , Butty SG , Juchau MR
Ref : Chemico-Biological Interactions , 18 :129 , 1977
Abstract : Berry_1977_Chem.Biol.Interact_18_129
ESTHER : Berry_1977_Chem.Biol.Interact_18_129
PubMedSearch : Berry_1977_Chem.Biol.Interact_18_129
PubMedID: 890843

Title : Phenytoin teratogenesis: correlation between embryopathic effect and covalent binding of putative arene oxide metabolite in gestational tissue - Martz_1977_J.Pharmacol.Exp.Ther_203_231
Author(s) : Martz F , Failinger C, 3rd , Blake DA
Ref : Journal of Pharmacology & Experimental Therapeutics , 203 :231 , 1977
Abstract : Martz_1977_J.Pharmacol.Exp.Ther_203_231
ESTHER : Martz_1977_J.Pharmacol.Exp.Ther_203_231
PubMedSearch : Martz_1977_J.Pharmacol.Exp.Ther_203_231
PubMedID: 909055

Title : Characterization of rat lung epoxide (styrene oxide) hydrase with a modified radioactive assay of improved sensitivity - Seidegard_1977_Cancer.Res_37_1075
Author(s) : Seidegard J , DePierre JW , Moron MS , Johannesen KA , Ernster L
Ref : Cancer Research , 37 :1075 , 1977
Abstract : Seidegard_1977_Cancer.Res_37_1075
ESTHER : Seidegard_1977_Cancer.Res_37_1075
PubMedSearch : Seidegard_1977_Cancer.Res_37_1075
PubMedID: 402999