pregnanediol glucuronide

{{Chembox

| ImageFile = Pregnanediol-3-glucuronide.svg

| ImageSize = 250px

| ImageAlt =

| IUPACName = (20S)-20-Hydroxy-5β-pregnan-3α-yl β-D-glucopyranosiduronic acid

| SystematicName = (2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-({(1S,3aS,3bR,5aR,7R,9aS,9bS,11aS)-1-[(1S)-1-hydroxyethyl]-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-yl}oxy)oxane-2-carboxylic acid

| OtherNames = Pregnanediol 3α-glucuronide; 5β-Pregnane-3α,20α-diol 3α-glucuronide

| Section1 = {{Chembox Identifiers

| CASNo = 38055-17-3

| ChEBI = 88765

| ChemSpiderID = 110346

| PubChem = 123796

| SMILES = C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)C)C)O

| StdInChI = 1S/C27H44O8/c1-13(28)17-6-7-18-16-5-4-14-12-15(8-10-26(14,2)19(16)9-11-27(17,18)3)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h13-23,25,28-31H,4-12H2,1-3H3,(H,32,33)/t13-,14+,15+,16-,17+,18-,19-,20-,21-,22+,23-,25+,26-,27+/m0/s1

| StdInChIKey = ZFFFJLDTCLJDHL-JQYCEVDMSA-N

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| Section2 = {{Chembox Properties

| C=27 | H=44 | O=8

| MolarMass = 496.641 g/mol

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| Section3 = {{Chembox Hazards

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Pregnanediol glucuronide, or 5β-pregnane-3α,20α-diol 3α-glucuronide, is the major metabolite of progesterone and the C3α glucuronide conjugate of pregnanediol (5β-pregnane-3α,20α-diol).{{cite book | first = J.B. | last = Josimovich | name-list-style = vanc | title = Gynecologic Endocrinology | url = https://books.google.com/books?id=9vv2BwAAQBAJ&pg=PA28|date=11 November 2013|publisher=Springer Science & Business Media|isbn=978-1-4613-2157-6|pages=28}}{{cite book|author1=Etienne-Emile Baulieu|author2=Paul A. Kelly|title=Hormones: From Molecules to Disease|url=https://books.google.com/books?id=Seddp4-dulIC&pg=PA401|date=30 November 1990|publisher=Springer Science & Business Media|isbn=978-0-412-02791-8|pages=401–}} Approximately 15 to 30% of a parenteral dose of progesterone is metabolized into pregnanediol glucuronide. While this specific isomer is referred to as pregnanediol glucuronide and is the most major form, there are actually many possible isomers of the metabolite.{{cite book | first = Perry T. | last = Cupps | name-list-style = vanc |title=Reproduction in Domestic Animals|url=https://books.google.com/books?id=bbb-ow0N7K4C&pg=PA101|date=20 February 1991|publisher=Elsevier|isbn=978-0-08-057109-6|pages=101–}}{{cite book|author=R. Hobkirk|title=Steroid Biochemistry|url=https://books.google.com/books?id=KL1HDwAAQBAJ&pg=PT23|date=18 January 2018|publisher=CRC Press|isbn=978-1-351-09380-4|pages=23–}}