1.0 2011-09-21 00:35:35 UTC 2015-07-21 06:57:54 UTC FDB023839 Naphthalene epoxide Naphthalene epoxide is an epoxide derivative of naphthalene. The toxicity of naphthalene has to do with the Phase I metabolism of this compound by cytochrome P450 monooxygenases. Deactivation of naphthalene involves epoxidation followed by glutathione conjugation and mercapturic acid formation. Naphthalene is stereoselectively metabolized to form (1R,2S)-Naphthalene epoxide and (1S,2R)-Naphthalene epoxide in the presence of CYP1A1 and CYP1A2, CYP2E1,CYP3A4 and CYP2A6. (PMID: 16959878) [HMDB] (1R,2S)-Naphthalene 1,2-oxide (1R,2S)-Naphthalene epoxide (1S,2R)-Naphthalene epoxide 1,2-Epoxy-1,2-dihydro-naphthalene 1,2-Epoxy-1,2-dihydronaphthalene Naphthalene 1,2-epoxide Naphthalene-1,2-oxide C10H8O 144.1699 144.057514878 1aH,7bH-naphtho[1,2-b]oxirene naphthalene 1,2-oxide 17180-88-0 O1C2C=CC3=CC=CC=C3C12 InChI=1S/C10H8O/c1-2-4-8-7(3-1)5-6-9-10(8)11-9/h1-6,9-10H XQIJIALOJPIKGX-UHFFFAOYSA-N belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Naphthalenes Organic compounds Benzenoids Naphthalenes Aromatic heteropolycyclic compounds Dialkyl ethers Epoxides Hydrocarbon derivatives Oxacyclic compounds Aromatic heteropolycyclic compound Dialkyl ether Ether Hydrocarbon derivative Naphthalene Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxirane arene epoxide Solid logp 1.89 ALOGPS logs -2.71 ALOGPS solubility 2.81e-01 g/l ALOGPS logp 2.16 ChemAxon pka_strongest_basic -4.3 ChemAxon iupac 1aH,7bH-naphtho[1,2-b]oxirene ChemAxon average_mass 144.1699 ChemAxon mono_mass 144.057514878 ChemAxon smiles O1C2C=CC3=CC=CC=C3C12 ChemAxon formula C10H8O ChemAxon inchi InChI=1S/C10H8O/c1-2-4-8-7(3-1)5-6-9-10(8)11-9/h1-6,9-10H ChemAxon inchikey XQIJIALOJPIKGX-UHFFFAOYSA-N ChemAxon polar_surface_area 9.23 ChemAxon refractivity 43.87 ChemAxon polarizability 15.26 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsIr 2377 Specdb::CMs 23077 Specdb::CMs 158844 Specdb::NmrOneD 258968 Specdb::NmrOneD 258969 Specdb::NmrOneD 258970 Specdb::NmrOneD 258971 Specdb::NmrOneD 258972 Specdb::NmrOneD 258973 Specdb::NmrOneD 258974 Specdb::NmrOneD 258975 Specdb::NmrOneD 258976 Specdb::NmrOneD 258977 Specdb::NmrOneD 258978 Specdb::NmrOneD 258979 Specdb::NmrOneD 258980 Specdb::NmrOneD 258981 Specdb::NmrOneD 258982 Specdb::NmrOneD 258983 Specdb::NmrOneD 258984 Specdb::NmrOneD 258985 Specdb::NmrOneD 258986 Specdb::NmrOneD 258987 Specdb::MsMs 82839 Specdb::MsMs 82840 Specdb::MsMs 82841 Specdb::MsMs 144309 Specdb::MsMs 144310 Specdb::MsMs 144311 Specdb::MsMs 2267762 Specdb::MsMs 2267763 Specdb::MsMs 2267764 Specdb::MsMs 3071880 Specdb::MsMs 3071881 Specdb::MsMs 3071882 HMDB06215 #<Reference:0x000055ce2f228f00> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Epoxide hydrolase 1 P07099 EPHX1 Glutathione S-transferase A1 P08263 GSTA1 Glutathione S-transferase A2 P09210 GSTA2 Glutathione S-transferase A3 Q16772 GSTA3 Glutathione S-transferase A4 O15217 GSTA4 Glutathione S-transferase A5 Q7RTV2 GSTA5 Glutathione S-transferase kappa 1 Q9Y2Q3 GSTK1 Glutathione S-transferase Mu 1 P09488 GSTM1 Glutathione S-transferase Mu 2 P28161 GSTM2 Glutathione S-transferase Mu 3 P21266 GSTM3 Glutathione S-transferase Mu 4 Q03013 GSTM4 Glutathione S-transferase Mu 5 P46439 GSTM5 Glutathione S-transferase omega-1 P78417 GSTO1 Glutathione S-transferase omega-2 Q9H4Y5 GSTO2 Glutathione S-transferase P P09211 GSTP1 Microsomal glutathione S-transferase 1 P10620 MGST1 Microsomal glutathione S-transferase 2 Q99735 MGST2 Microsomal glutathione S-transferase 3 O14880 MGST3