Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C24H30O8 |
| Molecular Weight | 446.4902 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O[C@@H]5O[C@@H]([C@@H](O)[C@H](O)[C@H]5O)C(O)=O)C=C4
InChI
InChIKey=FJAZVHYPASAQKM-JBAURARKSA-N
InChI=1S/C24H30O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,18+,19+,20-,21+,23-,24+/m1/s1
| Molecular Formula | C24H30O8 |
| Molecular Weight | 446.4902 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.wikigenes.org/e/chem/e/115255.html | https://en.wikipedia.org/wiki/Estrone_glucuronide
Curator's Comment: description was created based on several sources, including:
https://www.wikigenes.org/e/chem/e/115255.html | https://en.wikipedia.org/wiki/Estrone_glucuronide
Estrone glucuronide, or estrone-3-D-glucuronide is an endogenous steroid. It is formed from estrone in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by the kidneys. Early morning urine estrone-3-glucuronide assay is used in the monitoring of ovarian secretory function in precocious puberty. Estrone-3-glucuronide has also used for accurate detection of fertile period.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Steroid metabolism in the gonads of a patient with testicular feminization. II. Metabolism of c19- and c18-steroids in vitro. | 1976 Mar |
|
| Estrone and estradiol in patients with cirrhosis of the liver: effects of ACTH and dexamethasone. | 1976 Sep |
|
| Plasma-estrogens and liver cirrhosis. | 1979 Jul |
|
| Temporal relationships between indices of the fertile period. | 1983 May |
|
| Estrone- and dehydroepiandrosterone-sulfatase activities in human female epidermis. | 1985 |
|
| Adipose tissue as a source of hormones. | 1987 Jan |
|
| Estrone and estradiol concentrations in human ovaries, testes, and adrenals during the first two years of life. | 1987 Nov |
|
| Regulation of aromatase cytochrome P-450 and 17 beta-hydroxysteroid dehydrogenase messenger ribonucleic acid levels in choriocarcinoma cells. | 1992 Jan |
|
| Transport of beta-estradiol in freshly excised human skin in vitro: diffusion and metabolism in each skin layer. | 1994 Dec |
|
| Characterization of structural and functional properties of human 17 beta-hydroxysteroid dehydrogenase type 1 using recombinant enzymes and site-directed mutagenesis. | 1997 Jan |
|
| Regulation of cytochrome P450 cholesterol side-chain cleavage, 3 beta-hydroxysteroid dehydrogenase/delta 5-delta 4 isomerase type 1 and estradiol-17 beta-hydroxysteroid dehydrogenase mRNA levels by calcium in human choriocarcinoma JEG-3 cells. | 1997 Sep 30 |
|
| Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. | 2000 Oct |
|
| A transgenic mouse expressing human CYP1A2 in the pancreas. | 2000 Sep 15 |
|
| Urinary reproductive hormone level differences between African American and Caucasian women of reproductive age. | 2002 Aug |
|
| Prevalence of sarcopenia and predictors of skeletal muscle mass in healthy, older men and women. | 2002 Dec |
|
| The underlying basis for obesity: relationship to cancer. | 2002 Nov |
|
| Neuroprotective effects of estrone on NMDA-induced toxicity in primary cultures of rat cortical neurons are independent of estrogen receptors. | 2002 Nov-Dec |
|
| Differentiation-dependent expression of 17beta-hydroxysteroid dehydrogenase, type 10, in the rodent testis: effect of aging in Leydig cells. | 2003 Jul |
|
| Analysis and occurrence of estrogen in wastewater in Japan. | 2004 |
|
| Intercellular communication and human hepatocellular carcinoma. | 2004 Dec |
|
| Effects of testosterone on behavior, depression, and cognitive function in older men with mild cognitive loss. | 2004 Jan |
|
| Klotho is a novel beta-glucuronidase capable of hydrolyzing steroid beta-glucuronides. | 2004 Mar 12 |
|
| Delta-4-androstene-3,17-dione binds androgen receptor, promotes myogenesis in vitro, and increases serum testosterone levels, fat-free mass, and muscle strength in hypogonadal men. | 2005 Feb |
|
| Sex, hormones, and Alzheimer's disease. | 2005 Jun |
|
| Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis? | 2006 Apr |
|
| Characterization of type 12 17beta-hydroxysteroid dehydrogenase, an isoform of type 3 17beta-hydroxysteroid dehydrogenase responsible for estradiol formation in women. | 2006 Feb |
|
| Role of polymorphic human cytochrome P450 enzymes in estrone oxidation. | 2006 Mar |
|
| Investigation of keratinocyte regulation of collagen I synthesis by dermal fibroblasts in a simple in vitro model. | 2006 Mar |
Patents
Sample Use Guides
5 microCi of [14C]E2 and 10 microCi of [3H]estrone-3-glucuronide (E1-gluc).
Route of Administration:
Intravenous
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 06:48:50 GMT 2023
by
admin
on
Sat Dec 16 06:48:50 GMT 2023
|
| Record UNII |
933Q277TO2
|
| Record Status |
Validated (UNII)
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| Record Version |
|
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DTXSID20891497
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115255
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933Q277TO2
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2479-90-5
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Estrone-3-glucuronide
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28919
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admin on Sat Dec 16 06:48:50 GMT 2023 , Edited by admin on Sat Dec 16 06:48:50 GMT 2023
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