Pregnanediol glucuronide

Names
IUPAC name

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

Systematic IUPAC name

(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

Other names

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

Identifiers

CAS Number

* 38055-17-3

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:88765

ChemSpider |

* 110346

PubChem CID

* 123796

InChI

* InChI=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

Key: ZFFFJLDTCLJDHL-JQYCEVDMSA-N

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

Properties

Chemical formula

| C27H44O8
Molar mass | 496.641 g/mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

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).[1][2] Approximately 15 to 30% of a parenteral dose of progesterone is metabolized into pregnanediol glucuronide.[1][2] 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.[3][4]

## References

1. ↑ 1.0 1.1 Josimovich, J.B. (11 November 2013). Gynecologic Endocrinology. Springer Science & Business Media. pp. 28. ISBN 978-1-4613-2157-6. https://books.google.com/books?id=9vv2BwAAQBAJ&pg=PA28.
2. ↑ 2.0 2.1 Etienne-Emile Baulieu; Paul A. Kelly (30 November 1990). Hormones: From Molecules to Disease. Springer Science & Business Media. pp. 401–. ISBN 978-0-412-02791-8. https://books.google.com/books?id=Seddp4-dulIC&pg=PA401.
3. ↑ Cupps, Perry T. (20 February 1991). Reproduction in Domestic Animals. Elsevier. pp. 101–. ISBN 978-0-08-057109-6. https://books.google.com/books?id=bbb-ow0N7K4C&pg=PA101.
4. ↑ R. Hobkirk (18 January 2018). Steroid Biochemistry. CRC Press. pp. 23–. ISBN 978-1-351-09380-4. https://books.google.com/books?id=KL1HDwAAQBAJ&pg=PT23.

* v
* t
* e

Endogenous steroids

Precursors|

* Cholesterol
* 22R-Hydroxycholesterol
* 20α,22R-Dihydroxycholesterol
* Pregnenolone
* 11β-Hydroxypregnenolone
* 17α-Hydroxypregnenolone
* 21-Hydroxypregnenolone
* 17α,21-Dihydroxypregnenolone
* 11β,17α,21-Trihydroxypregnenolone

Corticosteroids|

| Glucocorticoids|

* 3α,5α-Tetrahydrocorticosterone
* 5α-Dihydrocorticosterone
* 11-Deoxycorticosterone
* 11-Deoxycortisol
* 11-Ketoprogesterone
* 21-Deoxycortisol
* 21-Deoxycortisone
* Corticosterone
* Cortisol
* Cortisone
* 17α-Hydroxypregnenolone
* 17α-Hydroxyprogesterone
* Pregnenolone
* Progesterone

* Metabolites: 5α-Dihydrocortisol
* 3α,5α-Tetrahydrocortisol

|

Mineralocorticoids|

* 5α-Dihydroaldosterone
* 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
* 11-Deoxycortisol
* 11-Deoxycorticosterone
* 11β-Hydroxyprogesterone (21-deoxycorticosterone)
* 18-Hydroxy-11-deoxycorticosterone
* 18-Hydroxycorticosterone
* 18-Hydroxyprogesterone
* Aldosterone
* Corticosterone
* Cortisol

Sex steroids|

| Androgens|

* 11-Ketodihydrotestosterone
* 11-Ketotestosterone
* 7β-Hydroxyepiandrosterone
* 11β-Hydroxyandrostenedione
* Adrenosterone (11-ketoandrostenedione)
* Androstenediol
* Androstenedione
* Androsterone
* Dehydroandrosterone
* DHEA
* DHEA sulfate
* Dihydrotestosterone
* Epiandrosterone
* Epitestosterone
* 16α-Hydroxyandrostenedione
* 16α-Hydroxy-DHEA
* 16α-Hydroxy-DHEA sulfate
* Testosterone

* Metabolites: 3α-Androstanediol
* 3α-Androstanediol glucuronide
* 3β-Androstanediol
* 5β-Dihydrotestosterone
* 3α-Etiocholanediol
* 3β-Etiocholanediol
* Androstanetriols
* Androstenediol sulfate
* Androsterone glucuronide
* Androsterone sulfate
* Dihydrotestosterone glucuronide
* Dihydrotestosterone sulfate
* Etiocholanedione
* Etiocholanolone
* Etiocholanolone glucuronide
* Epietiocholanolone
* Testosterone glucuronide
* Testosterone sulfate

|

Estrogens|

* Estranes: Estetrol
* Estradiol
* Estrone
* Estriol
* 17α-Estradiol
* 16β-Epiestriol (16β-hydroxyestradiol)
* 17α-Epiestriol (16α-hydroxy-17α-estradiol)
* 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
* 2-Hydroxyestradiol
* 2-Hydroxyestriol
* 2-Hydroxyestrone
* 4-Hydroxyestradiol
* 4-Hydroxyestriol
* 4-Hydroxyestrone
* 4-Methoxyestradiol
* 16α-Hydroxyestrone

* Others: 27-Hydroxycholesterol
* 3α-Androstanediol
* 3β-Androstanediol
* 4-Androstenedione
* 5-Androstenediol
* DHEA
* DHEA sulfate
* 7-Keto-DHEA
* 7α-Hydroxy-DHEA
* 16α-Hydroxy-DHEA

* Metabolites: 2-Methoxyestradiol
* 2-Methoxyestrone
* 4-Methoxyestrone
* Estradiol glucuronide
* Estradiol 3-glucuronide
* Estradiol sulfate
* Estradiol 17β-sulfate
* Estrone glucuronide
* Estrone sulfate
* Estriol glucuronide
* Estriol sulfate
* Lipoidal estradiol (e.g., estradiol stearate, estradiol palmitate)

Progestogens|

* Progesterone
* 16α-Hydroxyprogesterone
* 17α-Hydroxyprogesterone
* 20α-Dihydroprogesterone
* 20β-Dihydroprogesterone
* 5α-Dihydroprogesterone
* 11-Deoxycorticosterone
* 5α-DHDOC

* Metabolites: Allopregnanediol
* Pregnanediol
* Pregnanediol glucuronide
* Pregnanetriol

Neurosteroids|

* Cholestanes: 24S-Hydroxycholesterol
* Cholesterol

* Pregnanes: 3α-Dihydroprogesterone
* 3β-Dihydroprogesterone
* 5α-Dihydrocorticosterone
* 5α-Dihydroprogesterone
* 5β-Dihydroprogesterone
* Allopregnanolone
* Corticosterone
* DHC
* DHDOC
* 11-Deoxycorticosterone
* Epipregnanolone
* Isopregnanolone
* Pregnanolone
* Pregnenolone
* Pregnenolone sulfate
* Progesterone
* THB
* THDOC

* Androstanes: 3α-Androstanediol
* 3α-Androstenol
* 7-Keto-DHEA
* 7α-Hydroxy-DHEA
* 7β-Hydroxy-DHEA
* 7α-Hydroxyepiandrosterone
* 7β-Hydroxyepiandrosterone
* Androsterone
* DHEA
* DHEA sulfate
* Etiocholanolone

* Pheromones: 3α-Androstenol
* 3β-Androstenol
* Androstadienol
* Androstadienone
* Androstenone
* Androsterone
* Estratetraenol

Others|

* Vitamin D: 7-Dehydrocholesterol
* Calcidiol/Calcifediol
* Calcitriol
* Cholecalciferol

* Others: 7α-Hydroxycholesterol
* 11α-Hydroxyprogesterone
* 11β-Hydroxyprogesterone
* Cholesterol sulfate

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