1.0 2011-09-21 00:18:11 UTC 2015-10-09 22:29:42 UTC FDB022701 Ethenodeoxyadenosine Etheno (epsilon) modified DNA bases are generated from the carcinogens vinyl chloride and urethane, but also by reactions of DNA with products derived from lipid peroxidation (LPO) and oxidative stress via endogenous pathways. Highly variable background levels of epsilon-adducts were detected in DNA from different organs of unexposed humans and rodents. Several known cancer risk factors increased the level of these DNA lesions in target organs: elevated epsilon-adducts were found in hepatic DNA from patients with metal storage diseases, after overproduction of nitric oxide (NO) by inducible NO synthase (iNOS) in a mouse model, and in colonic polyps of familial adenomatous polyposis patients. A high omega-6-polyunsaturated fatty acid diet increased epsilon-DNA adducts in white blood cells of female subjects. (PMID: 10882861) [HMDB] 1,N(6)-Ethenodeoxyadenosine 1,N6-Etheno-2'-deoxyadenosine 1,N6-Etheno-dA 1,N6-Ethenodeoxyadenosine Ethenodeoxyadenosine N1,N6-Etheno-2'-deoxyadenosine C12H13N5O3 275.2633 275.101839307 (2R,3S,5R)-2-(hydroxymethyl)-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-3-ol ethenodeoxyadenosine 68498-25-9 OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CN1C=CN=C21 InChI=1S/C12H13N5O3/c18-4-8-7(19)3-9(20-8)17-6-14-10-11-13-1-2-16(11)5-15-12(10)17/h1-2,5-9,18-19H,3-4H2/t7-,8+,9+/m0/s1 XQQIMTUYVDUWKJ-DJLDLDEBSA-N belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring. Purines and purine derivatives Organic compounds Organoheterocyclic compounds Imidazopyrimidines Purines and purine derivatives Aromatic heteropolycyclic compounds Azacyclic compounds Heteroaromatic compounds Hydrocarbon derivatives N-substituted imidazoles Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Primary alcohols Pyrimidines and pyrimidine derivatives Secondary alcohols Tetrahydrofurans Alcohol Aromatic heteropolycyclic compound Azacycle Azole Heteroaromatic compound Hydrocarbon derivative Imidazole N-substituted imidazole Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Primary alcohol Purine Pyrimidine Secondary alcohol Tetrahydrofuran Solid logp -1.07 ALOGPS logs -1.66 ALOGPS solubility 5.98e+00 g/l ALOGPS logp -1.4 ChemAxon pka_strongest_acidic 13.89 ChemAxon pka_strongest_basic 4.96 ChemAxon iupac (2R,3S,5R)-2-(hydroxymethyl)-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-3-ol ChemAxon average_mass 275.2633 ChemAxon mono_mass 275.101839307 ChemAxon smiles OC[C@H]1O[C@H](C[C@@H]1O)N1C=NC2=C1N=CN1C=CN=C21 ChemAxon formula C12H13N5O3 ChemAxon inchi InChI=1S/C12H13N5O3/c18-4-8-7(19)3-9(20-8)17-6-14-10-11-13-1-2-16(11)5-15-12(10)17/h1-2,5-9,18-19H,3-4H2/t7-,8+,9+/m0/s1 ChemAxon inchikey XQQIMTUYVDUWKJ-DJLDLDEBSA-N ChemAxon polar_surface_area 97.7 ChemAxon refractivity 68.08 ChemAxon polarizability 27.1 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 10308 Specdb::CMs 38139 Specdb::CMs 169908 Specdb::NmrTwoD 1685 Specdb::MsMs 1681 Specdb::MsMs 1682 Specdb::MsMs 1683 Specdb::MsMs 288721 Specdb::MsMs 288722 Specdb::MsMs 288723 Specdb::MsMs 327931 Specdb::MsMs 327932 Specdb::MsMs 327933 Specdb::MsMs 2368923 Specdb::MsMs 2368924 Specdb::MsMs 2368925 Specdb::MsMs 2566781 Specdb::MsMs 2566782 Specdb::MsMs 2566783 Specdb::NmrOneD 1745 Specdb::NmrOneD 148300 Specdb::NmrOneD 148301 Specdb::NmrOneD 148302 Specdb::NmrOneD 148303 Specdb::NmrOneD 148304 Specdb::NmrOneD 148305 Specdb::NmrOneD 148306 Specdb::NmrOneD 148307 Specdb::NmrOneD 148308 Specdb::NmrOneD 148309 Specdb::NmrOneD 148310 Specdb::NmrOneD 148311 Specdb::NmrOneD 148312 Specdb::NmrOneD 148313 Specdb::NmrOneD 148314 Specdb::NmrOneD 148315 Specdb::NmrOneD 148316 Specdb::NmrOneD 148317 Specdb::NmrOneD 148318 Specdb::NmrOneD 148319 HMDB01786 #<Reference:0x000055ce3364b458> #<Reference:0x000055ce3364b2a0> #<Reference:0x000055ce3364b0c0> 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