1.0 2011-09-21 00:24:14 UTC 2015-07-21 06:57:29 UTC FDB023070 Androsterone glucuronide Androsterone 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 glucuronide 3alpha-Hydroxy-5alpha-androstan-17-one glucuronide 3α-hydroxy-5α-androstan-17-one glucuronide 5a-Androstan-3a-ol-17-one glucuronide Androsterone 3-glucuronide Androsterone glucosiduronate Androsterone glucosiduronic acid Androsterone glucuronoside Androsterone monoglucosiduronate b-D-17-oxo-5a-Androstan-3a-yl glucopyranosiduronic acid Etiocholanolone glucuronide C25H38O8 466.5644 466.256668192 (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 acid etiocholanolone glucuronide 1852-43-3 [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)=O InChI=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/s1 VFUIRAVTUVCQTF-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 conjugates Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Steroidal glycosides Aliphatic heteropolycyclic compounds 17-oxosteroids Acetals Androstane steroids Beta hydroxy acids and derivatives Carboxylic acids Hexoses Hydrocarbon derivatives Ketones Monocarboxylic acids and derivatives O-glucuronides O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Polyols Pyrans Secondary alcohols 1-o-glucuronide 17-oxosteroid Acetal Alcohol Aliphatic heteropolycyclic compound Androstane-skeleton Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Glucuronic acid or derivatives Glycosyl compound Hexose monosaccharide Hydrocarbon derivative Hydroxy acid Ketone Monocarboxylic acid or derivatives Monosaccharide O-glucuronide O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Oxosteroid Polyol Pyran Secondary alcohol Steroid-glucuronide-skeleton C19 steroids (androgens) and derivatives Glucuronides Glucuronides beta-D-glucosiduronic acid steroid glucosiduronic acid Solid logp 2.06 ALOGPS logs -3.14 ALOGPS solubility 3.35e-01 g/l ALOGPS logp 2.32 ChemAxon pka_strongest_acidic 3.47 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (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 acid ChemAxon average_mass 466.5644 ChemAxon mono_mass 466.256668192 ChemAxon smiles [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)=O ChemAxon formula C25H38O8 ChemAxon inchi InChI=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/s1 ChemAxon inchikey VFUIRAVTUVCQTF-BSOWLZGZSA-N ChemAxon polar_surface_area 133.52 ChemAxon refractivity 116.09 ChemAxon polarizability 50.56 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 8 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 47625 Specdb::MsMs 47626 Specdb::MsMs 47627 Specdb::MsMs 161631 Specdb::MsMs 161632 Specdb::MsMs 161633 Specdb::MsMs 2838963 Specdb::MsMs 2838964 Specdb::MsMs 2838965 Specdb::MsMs 2869773 Specdb::MsMs 2869774 Specdb::MsMs 2869775 Specdb::CMs 23615 Specdb::CMs 38483 Specdb::CMs 132234 Specdb::CMs 139968 HMDB02829 28832 #<Reference:0x000055ce31f37460> #<Reference:0x000055ce31f372a8> #<Reference:0x000055ce31f370f0> #<Reference:0x000055ce31f36f38> #<Reference:0x000055ce31f36d80> #<Reference:0x000055ce31f36bc8> #<Reference:0x000055ce31f36a10> #<Reference:0x000055ce31f36858> #<Reference:0x000055ce31f366a0> #<Reference:0x000055ce31f364e8> #<Reference:0x000055ce31f36330> #<Reference:0x000055ce31f36178> #<Reference:0x000055ce31f35fc0> #<Reference:0x000055ce31f35e08> #<Reference:0x000055ce31f35c50> #<Reference:0x000055ce31f35a98> #<Reference:0x000055ce31f358e0> #<Reference:0x000055ce31f35728> #<Reference:0x000055ce31f35570> #<Reference:0x000055ce31f353b8> #<Reference:0x000055ce31f35200> #<Reference:0x000055ce31f35048> #<Reference:0x000055ce31f34e90> #<Reference:0x000055ce31f34cd8> #<Reference:0x000055ce31f34b20> 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 1-10 Q9HAW8 UGT1A10 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 1-7 Q9HAW7 UGT1A7 UDP-glucuronosyltransferase 1-8 Q9HAW9 UGT1A8 UDP-glucuronosyltransferase 1-9 O60656 UGT1A9 UDP-glucuronosyltransferase 2A1 Q9Y4X1 UGT2A1 UDP-glucuronosyltransferase 2A3 Q6UWM9 UGT2A3 UDP-glucuronosyltransferase 2B10 P36537 UGT2B10 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