Estriol 3-glucuronide

{{short description|Chemical compound}}

{{Chembox

| ImageFile = Estriol 3-glucuronide.svg

| ImageSize = 250

| IUPACName = 16α,17β-Dihydroxyestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid

| SystematicName = (2S,3S,4S,5R,6S)-6-{[(1R,2R,3aS,3bR,9bS,11aS)-1,2-Dihydroxy-11a-methyl-2,3,3a,3b,4,5,9b,10,11,11a-decahydro-1H-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

| OtherNames = (16α,17β)-16,17-Dihydroxyestra-1(10),2,4-trien-3-yl β-D-glucopyranosiduronic acid

| Section1 = {{Chembox Identifiers

| CASNo = 2479-91-6

| ChEBI = 45869

| ChEMBL = 1236070

| KEGG = C11288

| PubChem = 443103

| ChemSpiderID = 391387

| SMILES = C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1C[C@H]([C@@H]2O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O

| InChI = 1/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-JRSYHJKYBO

| StdInChI = 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

| StdInChIKey = UZKIAJMSMKLBQE-JRSYHJKYSA-N

}}

| Section2 = {{Chembox Properties

| C=24 | H=32 | O=9

| Appearance =

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| Section3 = {{Chembox Hazards

| MainHazards =

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Estriol 3-glucuronide, or oestriol 3-glucuronide, also known as estriol 3-β-D-glucosiduronic acid, is a natural, steroidal estrogen and a glucuronic acid (β-D-glucopyranuronic acid) conjugate of estriol.{{cite book|author1=R.A. Hill|author2=H.L.J. Makin|author3=D.N. Kirk |author4=G.M. Murphy|title=Dictionary of Steroids|url=https://books.google.com/books?id=AI7EnUyeEtUC&pg=PA274|date=23 May 1991|publisher=CRC Press|isbn=978-0-412-27060-4|pages=274–}} It is found in the urine of women as a reversibly formed metabolite of estriol.{{cite book|author1=Michael Oettel|author2=Ekkehard Schillinger|title=Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen|url=https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA265|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-60107-1|pages=265–}}{{cite journal|last1=Musey|first1=Paul I.|last2=Kirdani|first2=Rashad Y.|last3=Bhanalaph|first3=Thongchai|last4=Sandberg|first4=Avery A.|title=Estriol metabolism in the baboon: Analysis of urinary and biliary metabolites|journal=Steroids|volume=22|issue=6|year=1973|pages=795–817|issn=0039-128X|doi=10.1016/0039-128X(73)90054-8|pmid=4203562}} The positional isomer of estriol 3-glucuronide, estriol 16α-glucuronide, also occurs as an endogenous metabolite of estriol, but to a much greater extent in comparison.