1.02011-09-21 00:23:30 UTC2015-07-21 06:57:29 UTCFDB023027Glycochenodeoxycholic acid 3-glucuronideGlycochenodeoxycholic 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-glucuronideC32H51NO11625.7474625.346211479(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 acid79254-98-1[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)=OInChI=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/s1ABFZMYIIUREPLL-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 conjugatesOrganic compoundsLipids and lipid-like moleculesSteroids and steroid derivativesSteroidal glycosidesAliphatic heteropolycyclic compounds7-hydroxysteroidsAcetalsBeta hydroxy acids and derivativesCarbonyl compoundsCarboxylic acidsCyclic alcohols and derivativesDicarboxylic acids and derivativesGlycinated bile acids and derivativesHexosesHydrocarbon derivativesMonohydroxy bile acids, alcohols and derivativesN-acyl aminesN-acyl-alpha amino acidsO-glucuronidesO-glycosyl compoundsOrganic oxidesOrganonitrogen compoundsOrganopnictogen compoundsOxacyclic compoundsOxanesPolyolsPyransSecondary alcoholsSecondary carboxylic acid amides1-o-glucuronide7-hydroxysteroidAcetalAlcoholAliphatic heteropolycyclic compoundAlpha-amino acid or derivativesBeta-hydroxy acidBile acid, alcohol, or derivativesCarbonyl groupCarboxamide groupCarboxylic acidCarboxylic acid derivativeCyclic alcoholDicarboxylic acid or derivativesFatty acylFatty amideGlucuronic acid or derivativesGlycinated bile acidGlycosyl compoundHexose monosaccharideHydrocarbon derivativeHydroxy acidHydroxy bile acid, alcohol, or derivativesHydroxysteroidMonohydroxy bile acid, alcohol, or derivativesMonosaccharideN-acyl-alpha amino acid or derivativesN-acyl-alpha-amino acidN-acyl-amineO-glucuronideO-glycosyl compoundOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundOxacycleOxanePolyolPyranSecondary alcoholSecondary carboxylic acid amideSteroid-glucuronide-skeletonSolidlogp1.48logs-3.94solubility7.22e-02 g/llogp1.16pka_strongest_acidic3.29pka_strongest_basic-0.61iupac(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 acidaverage_mass625.7474mono_mass625.346211479smiles[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)=OformulaC32H51NO11inchiInChI=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/s1inchikeyABFZMYIIUREPLL-ZWDGUQLWSA-Npolar_surface_area203.08refractivity154.36polarizability67.52rotatable_bond_count9acceptor_count11donor_count7physiological_charge-2formal_charge0Specdb::CMs19622Specdb::CMs566171Specdb::CMs566172Specdb::CMs566173Specdb::CMs566174Specdb::CMs566175Specdb::CMs566176Specdb::CMs566177Specdb::CMs566178Specdb::CMs566179Specdb::CMs566180Specdb::CMs566181Specdb::CMs566182Specdb::CMs566183Specdb::CMs566184Specdb::CMs566185Specdb::CMs566186Specdb::CMs566187Specdb::CMs566188Specdb::CMs566189Specdb::CMs566190Specdb::CMs566191Specdb::CMs566192Specdb::CMs566193Specdb::CMs566194Specdb::MsMs90087Specdb::MsMs90088Specdb::MsMs90089Specdb::MsMs153165Specdb::MsMs153166Specdb::MsMs153167Specdb::MsMs2659714Specdb::MsMs2659715Specdb::MsMs2659716Specdb::MsMs3019710Specdb::MsMs3019711Specdb::MsMs3019712HMDB02579#<Reference:0x000055567431dd30>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Beta-glucuronidaseP08236GUSBUDP-glucuronosyltransferase 1-1P22309UGT1A1UDP-glucuronosyltransferase 1-3P35503UGT1A3UDP-glucuronosyltransferase 1-4P22310UGT1A4UDP-glucuronosyltransferase 1-5P35504UGT1A5UDP-glucuronosyltransferase 1-6P19224UGT1A6UDP-glucuronosyltransferase 1-9O60656UGT1A9UDP-glucuronosyltransferase 2A1Q9Y4X1UGT2A1UDP-glucuronosyltransferase 2A3Q6UWM9UGT2A3UDP-glucuronosyltransferase 2B11O75310UGT2B11UDP-glucuronosyltransferase 2B15P54855UGT2B15UDP-glucuronosyltransferase 2B17O75795UGT2B17UDP-glucuronosyltransferase 2B28Q9BY64UGT2B28UDP-glucuronosyltransferase 2B4P06133UGT2B4UDP-glucuronosyltransferase 2B7P16662UGT2B7