ESTRONE GLUCURONIDE

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

Structure Search

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(O[C@@H]5O[C@@H]([C@@H](O)[C@H](O)[C@H]5O)C(O)=O)=C4)[C@@H]1CCC2=O

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1755456
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

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 134 Target ID: CHEMBL206 Sources: https://www.google.ch/patents/US6962808	Agonist 2752
UDP-glucuronosyltransferase 1-3 6 Target ID: CHEMBL3542435 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11154740	Substrate 661
UDP-glucuronosyltransferase 1-9 11 Target ID: CHEMBL1743319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11154740 \| https://www.ncbi.nlm.nih.gov/pubmed/8095226	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Precocious puberty 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7629394	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown
Fertile period 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14742773	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Stimulation of estradiol glucuronidation: a protective mechanism against estradiol-mediated carcinogenesis?	2006-04	16598814
Role of polymorphic human cytochrome P450 enzymes in estrone oxidation.	2006-03	16537715
Investigation of keratinocyte regulation of collagen I synthesis by dermal fibroblasts in a simple in vitro model.	2006-03	16445767
Characterization of type 12 17beta-hydroxysteroid dehydrogenase, an isoform of type 3 17beta-hydroxysteroid dehydrogenase responsible for estradiol formation in women.	2006-02	16166196
Sex, hormones, and Alzheimer's disease.	2005-06	15983176
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.	2005-02	15522925
Intercellular communication and human hepatocellular carcinoma.	2004-12	15650246
Klotho is a novel beta-glucuronidase capable of hydrolyzing steroid beta-glucuronides.	2004-03-12	14701853
Effects of testosterone on behavior, depression, and cognitive function in older men with mild cognitive loss.	2004-01	14718489
Analysis and occurrence of estrogen in wastewater in Japan.	2004	15499675
Neuroprotective effects of estrone on NMDA-induced toxicity in primary cultures of rat cortical neurons are independent of estrogen receptors.	2003-07-18	12866733
Differentiation-dependent expression of 17beta-hydroxysteroid dehydrogenase, type 10, in the rodent testis: effect of aging in Leydig cells.	2003-07	12810569
Prevalence of sarcopenia and predictors of skeletal muscle mass in healthy, older men and women.	2002-12	12456735
The underlying basis for obesity: relationship to cancer.	2002-11	12421869
Urinary reproductive hormone level differences between African American and Caucasian women of reproductive age.	2002-08	12137878
Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa.	2000-10	10997942
A transgenic mouse expressing human CYP1A2 in the pancreas.	2000-09-15	10930541
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.	1997-09-30	9359473
Characterization of structural and functional properties of human 17 beta-hydroxysteroid dehydrogenase type 1 using recombinant enzymes and site-directed mutagenesis.	1997-01	8994190
Transport of beta-estradiol in freshly excised human skin in vitro: diffusion and metabolism in each skin layer.	1994-12	7899244
Regulation of aromatase cytochrome P-450 and 17 beta-hydroxysteroid dehydrogenase messenger ribonucleic acid levels in choriocarcinoma cells.	1992-01	1309352
Estrone and estradiol concentrations in human ovaries, testes, and adrenals during the first two years of life.	1987-11	3667883
Adipose tissue as a source of hormones.	1987-01	3541569
Estrone- and dehydroepiandrosterone-sulfatase activities in human female epidermis.	1985	3160310
Temporal relationships between indices of the fertile period.	1983-05	6840308
Plasma-estrogens and liver cirrhosis.	1979-07	224606
Estrone and estradiol in patients with cirrhosis of the liver: effects of ACTH and dexamethasone.	1976-09	182710
Steroid metabolism in the gonads of a patient with testicular feminization. II. Metabolism of c19- and c18-steroids in vitro.	1976-03	1244196

Patents

Sample Use Guides

In Vivo Use Guide

5 microCi of [14C]E2 and 10 microCi of [3H]estrone-3-glucuronide (E1-gluc).

Route of Administration: Intravenous

In Vitro Use Guide

Estrone-3-glucuronide (2.51 pmol) were incubated for 5,10, 30,60, and 90 minutes at 37°C with 50 mg lignin in 0.1 M phosphate buffer (pH 7.0). 21% of the estrone glucuronide had been bound to lignin.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:38:16 GMT 2025` Edited by `admin` on `Mon Mar 31 21:38:16 GMT 2025`
Record UNII	933Q277TO2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

.BETA.-D-GLUCOPYRANOSIDURONIC ACID, 17-OXOESTRA-1,3,5(10)-TRIEN-3-YL

Preferred Name

English

ESTRONE GLUCURONIDE

Common Name

English

ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-(.BETA.-D-GLUCOPYRANURONOSYLOXY)-

Common Name

English

ESTRONE .BETA.-GLUCURONIDE

Common Name

English

GLUCOPYRANOSIDURONIC ACID, 17-OXOESTRA-1,3,5(10)-TRIEN-3-YL, .BETA.-D-

Common Name

English

.BETA.-D-GLUCOSIDURONIC ACID, 17-OXOESTRA-1,3,5(10)-TRIEN-3-YL

Common Name

English

ESTRONE MONOGLUCOSIDURONATE

Common Name

English

ESTRONE 3-GLUCURONIDE

Common Name

English

ESTRONE .BETA.-D-GLUCURONIDE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID20891497