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

[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

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 127 Target ID: CHEMBL206 Sources: https://www.google.ch/patents/US6962808	Agonist 2678
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
Estrone and estradiol in patients with cirrhosis of the liver: effects of ACTH and dexamethasone.	1976 Sep	182710
Temporal relationships between indices of the fertile period.	1983 May	6840308
Estrone- and dehydroepiandrosterone-sulfatase activities in human female epidermis.	1985	3160310
Adipose tissue as a source of hormones.	1987 Jan	3541569
Regulation of aromatase cytochrome P-450 and 17 beta-hydroxysteroid dehydrogenase messenger ribonucleic acid levels in choriocarcinoma cells.	1992 Jan	1309352
Transport of beta-estradiol in freshly excised human skin in vitro: diffusion and metabolism in each skin layer.	1994 Dec	7899244
Characterization of structural and functional properties of human 17 beta-hydroxysteroid dehydrogenase type 1 using recombinant enzymes and site-directed mutagenesis.	1997 Jan	8994190
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	9359473
A transgenic mouse expressing human CYP1A2 in the pancreas.	2000 Sep 15	10930541
Urinary reproductive hormone level differences between African American and Caucasian women of reproductive age.	2002 Aug	12137878
The underlying basis for obesity: relationship to cancer.	2002 Nov	12421869
Analysis and occurrence of estrogen in wastewater in Japan.	2004	15499675
Intercellular communication and human hepatocellular carcinoma.	2004 Dec	15650246
Klotho is a novel beta-glucuronidase capable of hydrolyzing steroid beta-glucuronides.	2004 Mar 12	14701853
Sex, hormones, and Alzheimer's disease.	2005 Jun	15983176
Characterization of type 12 17beta-hydroxysteroid dehydrogenase, an isoform of type 3 17beta-hydroxysteroid dehydrogenase responsible for estradiol formation in women.	2006 Feb	16166196

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 `Sat Dec 16 06:48:50 GMT 2023` Edited by `admin` on `Sat Dec 16 06:48:50 GMT 2023`
Record UNII	933Q277TO2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

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

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