1.0 2011-09-21 00:23:30 UTC 2015-07-21 06:57:29 UTC FDB023027 Glycochenodeoxycholic acid 3-glucuronide Glycochenodeoxycholic acid (GCDC)induced the mitochondrial permeability transition (MPT) in a dose-dependent manner, which was inhibited by cyclosporin A, alpha-tocopherol, beta-carotene and idebenone. GCDC stimulated reactive oxygen species generation and release of cytochrome c and apoptosis-inducing factor, which were significantly inhibited by the antioxidants, cyclosporin A, and tauroursodeoxycholic acid. mitochondrial pathways of cell death are stimulated in human hepatic mitochondria exposed to GCDC consistent with the role of mitochondrial dysfunction in the pathogenesis of cholestatic liver injury. (16056106) [HMDB] Glycochenodeoxycholic acid 3-glucuronide C32H51NO11 625.7474 625.346211479 (2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R)-14-[(2R)-4-[(carboxymethyl)carbamoyl]butan-2-yl]-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R)-14-[(2R)-4-(carboxymethylcarbamoyl)butan-2-yl]-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid 79254-98-1 [H][C@@]12CCC([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O InChI=1S/C32H51NO11/c1-15(4-7-22(35)33-14-23(36)37)18-5-6-19-24-20(9-11-32(18,19)3)31(2)10-8-17(12-16(31)13-21(24)34)43-30-27(40)25(38)26(39)28(44-30)29(41)42/h15-21,24-28,30,34,38-40H,4-14H2,1-3H3,(H,33,35)(H,36,37)(H,41,42)/t15-,16+,17-,18?,19+,20+,21-,24+,25+,26+,27-,28+,30-,31+,32-/m1/s1 ABFZMYIIUREPLL-ZWDGUQLWSA-N belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. Steroid glucuronide conjugates Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Steroidal glycosides Aliphatic heteropolycyclic compounds 7-hydroxysteroids Acetals Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Dicarboxylic acids and derivatives Glycinated bile acids and derivatives Hexoses Hydrocarbon derivatives Monohydroxy bile acids, alcohols and derivatives N-acyl amines N-acyl-alpha amino acids O-glucuronides O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Pyrans Secondary alcohols Secondary carboxylic acid amides 1-o-glucuronide 7-hydroxysteroid Acetal Alcohol Aliphatic heteropolycyclic compound Alpha-amino acid or derivatives Beta-hydroxy acid Bile acid, alcohol, or derivatives Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Dicarboxylic acid or derivatives Fatty acyl Fatty amide Glucuronic acid or derivatives Glycinated bile acid Glycosyl compound Hexose monosaccharide Hydrocarbon derivative Hydroxy acid Hydroxy bile acid, alcohol, or derivatives Hydroxysteroid Monohydroxy bile acid, alcohol, or derivatives Monosaccharide N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine O-glucuronide O-glycosyl compound Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Oxane Polyol Pyran Secondary alcohol Secondary carboxylic acid amide Steroid-glucuronide-skeleton Solid logp 1.48 ALOGPS logs -3.94 ALOGPS solubility 7.22e-02 g/l ALOGPS logp 1.16 ChemAxon pka_strongest_acidic 3.29 ChemAxon pka_strongest_basic -0.61 ChemAxon iupac (2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R)-14-[(2R)-4-[(carboxymethyl)carbamoyl]butan-2-yl]-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid ChemAxon average_mass 625.7474 ChemAxon mono_mass 625.346211479 ChemAxon smiles [H][C@@]12CCC([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](O)C[C@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O ChemAxon formula C32H51NO11 ChemAxon inchi InChI=1S/C32H51NO11/c1-15(4-7-22(35)33-14-23(36)37)18-5-6-19-24-20(9-11-32(18,19)3)31(2)10-8-17(12-16(31)13-21(24)34)43-30-27(40)25(38)26(39)28(44-30)29(41)42/h15-21,24-28,30,34,38-40H,4-14H2,1-3H3,(H,33,35)(H,36,37)(H,41,42)/t15-,16+,17-,18?,19+,20+,21-,24+,25+,26+,27-,28+,30-,31+,32-/m1/s1 ChemAxon inchikey ABFZMYIIUREPLL-ZWDGUQLWSA-N ChemAxon polar_surface_area 203.08 ChemAxon refractivity 154.36 ChemAxon polarizability 67.52 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 11 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 90087 Specdb::MsMs 90088 Specdb::MsMs 90089 Specdb::MsMs 153165 Specdb::MsMs 153166 Specdb::MsMs 153167 Specdb::MsMs 2659714 Specdb::MsMs 2659715 Specdb::MsMs 2659716 Specdb::MsMs 3019710 Specdb::MsMs 3019711 Specdb::MsMs 3019712 Specdb::CMs 19622 Specdb::CMs 566171 Specdb::CMs 566172 Specdb::CMs 566173 Specdb::CMs 566174 Specdb::CMs 566175 Specdb::CMs 566176 Specdb::CMs 566177 Specdb::CMs 566178 Specdb::CMs 566179 Specdb::CMs 566180 Specdb::CMs 566181 Specdb::CMs 566182 Specdb::CMs 566183 Specdb::CMs 566184 Specdb::CMs 566185 Specdb::CMs 566186 Specdb::CMs 566187 Specdb::CMs 566188 Specdb::CMs 566189 Specdb::CMs 566190 Specdb::CMs 566191 Specdb::CMs 566192 Specdb::CMs 566193 Specdb::CMs 566194 HMDB02579 #<Reference:0x00007f093c12b7d0> 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 Beta-glucuronidase P08236 GUSB UDP-glucuronosyltransferase 1-1 P22309 UGT1A1 UDP-glucuronosyltransferase 1-3 P35503 UGT1A3 UDP-glucuronosyltransferase 1-4 P22310 UGT1A4 UDP-glucuronosyltransferase 1-5 P35504 UGT1A5 UDP-glucuronosyltransferase 1-6 P19224 UGT1A6 UDP-glucuronosyltransferase 1-9 O60656 UGT1A9 UDP-glucuronosyltransferase 2A1 Q9Y4X1 UGT2A1 UDP-glucuronosyltransferase 2A3 Q6UWM9 UGT2A3 UDP-glucuronosyltransferase 2B11 O75310 UGT2B11 UDP-glucuronosyltransferase 2B15 P54855 UGT2B15 UDP-glucuronosyltransferase 2B17 O75795 UGT2B17 UDP-glucuronosyltransferase 2B28 Q9BY64 UGT2B28 UDP-glucuronosyltransferase 2B4 P06133 UGT2B4 UDP-glucuronosyltransferase 2B7 P16662 UGT2B7