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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O3
Molecular Weight 286.3662
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 16.ALPHA.-HYDROXYESTRONE

SMILES

C[C@@]12CC[C@]3([H])c4ccc(cc4CC[C@@]3([H])[C@]2([H])C[C@]([H])(C1=O)O)O

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 286.3662
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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

PubMed

PubMed

TitleDatePubMed
Biological properties of 16 alpha-hydroxyestrone: implications in estrogen physiology and pathophysiology.
1980 Sep
Covalent binding of the endogenous estrogen 16 alpha-hydroxyestrone to estradiol receptor in human breast cancer cells: characterization and intranuclear localization.
1988 Nov
Estrogen hydroxylation--the good and the bad.
2009 Feb
Patents

Patents

Sample Use Guides

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 Jun 26 00:42:25 UTC 2021
Edited
by admin
on Sat Jun 26 00:42:25 UTC 2021
Record UNII
JY611949JU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
16.ALPHA.-HYDROXYESTRONE
Common Name English
(16R)-3,16.ALPHA.-DIHYDROXY-1,3,5(10)-ESTRATRIEN-17-ONE
Systematic 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
HYDROXYESTRONE [WHO-DD]
Common 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
Created by admin on Sat Jun 26 00:42:25 UTC 2021 , Edited by admin on Sat Jun 26 00:42:25 UTC 2021
Code System Code Type Description
FDA UNII
JY611949JU
Created by admin on Sat Jun 26 00:42:25 UTC 2021 , Edited by admin on Sat Jun 26 00:42:25 UTC 2021
PRIMARY
PUBCHEM
115116
Created by admin on Sat Jun 26 00:42:25 UTC 2021 , Edited by admin on Sat Jun 26 00:42:25 UTC 2021
PRIMARY
CAS
566-76-7
Created by admin on Sat Jun 26 00:42:25 UTC 2021 , Edited by admin on Sat Jun 26 00:42:25 UTC 2021
PRIMARY
NCI_THESAURUS
C120468
Created by admin on Sat Jun 26 00:42:25 UTC 2021 , Edited by admin on Sat Jun 26 00:42:25 UTC 2021
PRIMARY NCIT
EVMPD
SUB14145MIG
Created by admin on Sat Jun 26 00:42:25 UTC 2021 , Edited by admin on Sat Jun 26 00:42:25 UTC 2021
PRIMARY
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