16.ALPHA.-HYDROXYESTRONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H22O3
Molecular Weight	286.3655
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4

InChI

InChIKey=WPOCIZJTELRQMF-QFXBJFAPSA-N

InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H22O3
Molecular Weight	286.3655
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3186693 | https://www.ncbi.nlm.nih.gov/pubmed/6325410 | https://www.ncbi.nlm.nih.gov/pubmed/24784887 | http://www.creative-diagnostics.com/ESTRAMET-2-16-ELISA-Kit-188220-465.htm

16alpha-hydroxyestrone is a naturally occurring estrone metabolite. It exerts estrogenic properties through covalent estrogen receptor (ER) binding. 16alpha-hydroxyestrone is a potential tumor initiator. The ratio 2-hydroxyestrone to 16alpha-hydroxyestrone could serve as an innovative intermediate biomarker for breast cancer risk. This biomarker could be used to identify women at high risk, and provide the analytic framework for the development of new pharmaceutical and dietary intervention strategies.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor 75 Target ID: CHEMBL2093866 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3186693 \| https://www.ncbi.nlm.nih.gov/pubmed/6325410	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24784887 http://www.creative-diagnostics.com/ESTRAMET-2-16-ELISA-Kit-188220-465.htm	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Covalent binding of the endogenous estrogen 16 alpha-hydroxyestrone to estradiol receptor in human breast cancer cells: characterization and intranuclear localization.	1988 Nov	3186693
Estrogen hydroxylation--the good and the bad.	2009 Feb	19250192

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The ovarian cancer cell line OVCAR-3 were incubated with 16alpha-hydroxyestrone (16-OHE1) for seven days in the concentration range of 0.01 nM to 10 nM. 16-OHE1 treatment exerts the proliferative and antiapoptotic effect.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:20:09 GMT 2023` Edited by `admin` on `Sat Dec 16 08:20:09 GMT 2023`
Record UNII	JY611949JU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

16.ALPHA.-HYDROXYESTRONE

Common Name

English

(16R)-3,16.ALPHA.-DIHYDROXY-1,3,5(10)-ESTRATRIEN-17-ONE

Systematic Name

English

Hydroxyestrone [WHO-DD]

Common Name

English

C05300

Code

English

16.ALPHA.-OHE1

Common Name

English

(8R,9S,13S,14S,16R)-3,16-DIHYDROXY-13-METHYL-7,8,9,11,12,14,15,16-OCTAHYDRO-6H-CYCLOPENTA(A)PHENANTHREN-17-ONE

Systematic Name

English

J130.683I

Code

English

3,16.ALPHA.-DIHYDROXY-1,3,5(10)-ESTRATRIEN-17-ONE

Systematic Name

English

ESTRA-1,3,5(10)-TRIENE-3,16.ALPHA.-DIOL-17-ONE

Systematic Name

English

16ALPHA-HYDROXYESTRONE

Common Name

English

ESTRA-1,3,5(10)-TRIEN-17-ONE, 3,16-DIHYDROXY-, (16.ALPHA.)-

Systematic Name

English

(16.ALPHA.)-3,16-DIHYDROXYESTRA-1(10),2,4-TRIEN-17-ONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2181