1.02011-09-21 00:24:14 UTC2015-07-21 06:57:29 UTCFDB023070Androsterone glucuronideAndrosterone glucuronide (ADT-G) is one of the major circulating C19-steroid metabolites in humans. Human and monkey are unique in having high levels of circulating ADT-G. Furthermore, the plasma levels of these glucuronide derivatives reflect the peripheral tissue conversion of adrenal and gonadal precursor C19-steroids to active androgens in various pathophysiological conditions. Identification and characterization of human UDP-glucuronosyltransferase 2B (UGT2Bs) demonstrated the major role that these enzymes play in androgen conjugation, with UGT2B15 and UGT2B17 (EC 2.4.1.17) being the major androsterone-conjugating isoforms. Exaggerated androsterone metabolism, is observed in hyper-androgenic as well as in some normo-androgenic women with acne and androsterone glucuronide could be a marker in differentiating acne and hirsutism in hyperandrogenic women. Present data shows that the most practical and probably only valid means of assessing androgenic activity in women is to measure ADT-G, the metabolite that accounts for 93% of the total androgen glucuronide derivatives. (PMID: 12943709, 12445184, 16621522) [HMDB]3a-Hydroxy-5a-androstan-17-one glucuronide3alpha-Hydroxy-5alpha-androstan-17-one glucuronide3α-hydroxy-5α-androstan-17-one glucuronide5a-Androstan-3a-ol-17-one glucuronideAndrosterone 3-glucuronideAndrosterone glucosiduronateAndrosterone glucosiduronic acidAndrosterone glucuronosideAndrosterone monoglucosiduronateb-D-17-oxo-5a-Androstan-3a-yl glucopyranosiduronic acidEtiocholanolone glucuronideC25H38O8466.5644466.256668192(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acidetiocholanolone glucuronide1852-43-3[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[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/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1VFUIRAVTUVCQTF-BSOWLZGZSA-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 compounds17-oxosteroidsAcetalsAndrostane steroidsBeta hydroxy acids and derivativesCarboxylic acidsHexosesHydrocarbon derivativesKetonesMonocarboxylic acids and derivativesO-glucuronidesO-glycosyl compoundsOrganic oxidesOxacyclic compoundsOxanesPolyolsPyransSecondary alcohols1-o-glucuronide17-oxosteroidAcetalAlcoholAliphatic heteropolycyclic compoundAndrostane-skeletonBeta-hydroxy acidCarbonyl groupCarboxylic acidCarboxylic acid derivativeGlucuronic acid or derivativesGlycosyl compoundHexose monosaccharideHydrocarbon derivativeHydroxy acidKetoneMonocarboxylic acid or derivativesMonosaccharideO-glucuronideO-glycosyl compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxaneOxosteroidPolyolPyranSecondary alcoholSteroid-glucuronide-skeletonC19 steroids (androgens) and derivativesGlucuronidesGlucuronidesbeta-D-glucosiduronic acidsteroid glucosiduronic acidSolidlogp2.06logs-3.14solubility3.35e-01 g/llogp2.32pka_strongest_acidic3.47pka_strongest_basic-3.7iupac(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acidaverage_mass466.5644mono_mass466.256668192smiles[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[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)=OformulaC25H38O8inchiInChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1inchikeyVFUIRAVTUVCQTF-BSOWLZGZSA-Npolar_surface_area133.52refractivity116.09polarizability50.56rotatable_bond_count3acceptor_count8donor_count4physiological_charge-1formal_charge0Specdb::CMs23615Specdb::CMs38483Specdb::CMs132234Specdb::CMs139968Specdb::MsMs47625Specdb::MsMs47626Specdb::MsMs47627Specdb::MsMs161631Specdb::MsMs161632Specdb::MsMs161633Specdb::MsMs2838963Specdb::MsMs2838964Specdb::MsMs2838965Specdb::MsMs2869773Specdb::MsMs2869774Specdb::MsMs2869775HMDB0282928832#<Reference:0x00005556755dcc78>#<Reference:0x00005556755dcac0>#<Reference:0x00005556755dc908>#<Reference:0x00005556755dc750>#<Reference:0x00005556755dc598>#<Reference:0x00005556755dc390>#<Reference:0x00005556755dc1d8>#<Reference:0x00005556755dc020>#<Reference:0x00005556755dbd78>#<Reference:0x00005556755dbaf8>#<Reference:0x00005556755db8a0>#<Reference:0x00005556755db6e8>#<Reference:0x00005556755db4e0>#<Reference:0x00005556755db328>#<Reference:0x00005556755db0f8>#<Reference:0x00005556755daf18>#<Reference:0x00005556755dacc0>#<Reference:0x00005556755daa18>#<Reference:0x00005556755da860>#<Reference:0x00005556755da6a8>#<Reference:0x00005556755da4a0>#<Reference:0x00005556755da2c0>#<Reference:0x00005556755da0b8>#<Reference:0x00005556755d9e88>#<Reference:0x00005556755d9c80>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 1-10Q9HAW8UGT1A10UDP-glucuronosyltransferase 1-3P35503UGT1A3UDP-glucuronosyltransferase 1-4P22310UGT1A4UDP-glucuronosyltransferase 1-5P35504UGT1A5UDP-glucuronosyltransferase 1-6P19224UGT1A6UDP-glucuronosyltransferase 1-7Q9HAW7UGT1A7UDP-glucuronosyltransferase 1-8Q9HAW9UGT1A8UDP-glucuronosyltransferase 1-9O60656UGT1A9UDP-glucuronosyltransferase 2A1Q9Y4X1UGT2A1UDP-glucuronosyltransferase 2A3Q6UWM9UGT2A3UDP-glucuronosyltransferase 2B10P36537UGT2B10UDP-glucuronosyltransferase 2B11O75310UGT2B11UDP-glucuronosyltransferase 2B15P54855UGT2B15UDP-glucuronosyltransferase 2B17O75795UGT2B17UDP-glucuronosyltransferase 2B28Q9BY64UGT2B28UDP-glucuronosyltransferase 2B4P06133UGT2B4UDP-glucuronosyltransferase 2B7P16662UGT2B7