CHEBI:137701 - 17-epiestriol 3-O-(β-D-glucuronide)

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ChEBI Name 17-epiestriol 3-O-(β-D-glucuronide) ChEBI ID CHEBI:137701 ChEBI ASCII Name 17-epiestriol 3-O-(beta-D-glucuronide) Definition A steroid glucosiduronic acid that is 17-epiestriol having a single β-D-glucuronic acid residue attached at position 3. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information ZINC000299854151 Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C24H32O9 Net Charge 0 Average Mass 464.506 Monoisotopic Mass 464.20463 InChI InChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(32-23-19(28)17(26)18(27)20(33-23)22(30)31)8-10(12)2-4-14(13)15(24)9-16(25)21(24)29/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16-,17+,18+,19-,20+,21-,23-,24+/m1/s1 InChIKey UZKIAJMSMKLBQE-PHEYUCJMSA-N SMILES C1=C2C(CC[C@]3([C@@]4(C[C@H]([C@H]([C@]4(CC[C@@]32[H])C)O)O)[H])[H])=CC(=C1)O[C@@H]5O[C@@H]([C@H]([C@@H]([C@H]5O)O)O)C(O)=O ChEBI Ontology Outgoing 17-epiestriol 3-O-(β-D-glucuronide) (CHEBI:137701) has functional parent 17-epiestriol (CHEBI:42156) 17-epiestriol 3-O-(β-D-glucuronide) (CHEBI:137701) is a β-D-glucosiduronic acid (CHEBI:15341) 17-epiestriol 3-O-(β-D-glucuronide) (CHEBI:137701) is a steroid glucosiduronic acid (CHEBI:26763) 17-epiestriol 3-O-(β-D-glucuronide) (CHEBI:137701) is conjugate acid of 17-epiestriol 3-O-(β-D-glucuronide)(1−) (CHEBI:136882) Incoming 17-epiestriol 3-O-(β-D-glucuronide)(1−) (CHEBI:136882) is conjugate base of 17-epiestriol 3-O-(β-D-glucuronide) (CHEBI:137701) IUPAC Name 16α,17α-dihydroxyestra-1(10),2,4-trien-3-yl β-D-glucopyranosiduronic acid Synonyms Sources (16α,17α)-16,17-dihydroxyestra-1(10),2,4-trien-3-yl β-D-glucopyranosiduronic acid IUPAC 16α,17α-estriol 3-O-(β-D-glucuronate) ChEBI Registry Number Type Source 23416853 Reaxys Registry Number Reaxys Citation Sneitz N, Vahermo M, Mosorin J, Laakkonen L, Poirier D, Finel M (2013) Regiospecificity and stereospecificity of human UDP-glucuronosyltransferases in the glucuronidation of estriol, 16-epiestriol, 17-epiestriol, and 13-epiestradiol. Drug metabolism and disposition: the biological fate of chemicals 41, 582-591 [PubMed:23288867] [show Abstract] The glucuronidation of estriol, 16-epiestriol, and 17-epiestriol by the human UDP-glucuronosyltransferases (UGTs) of subfamilies 1A, 2A, and 2B was examined. UGT1A10 is highly active in the conjugation of the 3-OH in all these estriols, whereas UGT2B7 is the most active UGT toward one of the ring D hydroxyls, the 16-OH in estriol and 16-epiestriol, but the 17-OH in 17-epiestriol. Kinetic analyses indicated that the 17-OH configuration plays a major role in the affinity of UGT2B7 for estrogens. The glucuronidation of the different estriols by the human liver and intestine microsomes reflects the activity of UGT1A10 and UGT2B7 in combination with the tissues' difference in UGT1A10 expression. The UGT1A10 mutant 1A10-F93G exhibited much higher V(max) values than UGT1A10 in estriol and 17-epiestriol glucuronidation, but a significantly lower value in 16-epiestriol glucuronidation. To this study on estriol glucuronidation we have added experiments with 13-epiestradiol, a synthetic estradiol in which the spatial arrangement of the methyl on C18 and the hydroxyl on C17 is significantly different than in other estrogens. In comparison with estradiol glucuronidation, the C13 configuration change decreases the turnover of UGTs that conjugate the 3-OH, but increases it in UGTs that primarily conjugate the 17-OH. Unexpectedly, UGT2B17 exhibited similar conjugation rates of both the 17-OH and 3-OH of 13-espiestradiol. The combined results reveal the strong preference of UGT1A10 for the 3-OH of physiologic estrogens and the equivalently strong preference of UGT2B7 and UGT2B17 for the hydroxyls on ring D of such steroid hormones. Last Modified 10 July 2017