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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O3
Molecular Weight 286.3655
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-HYDROXYESTRONE

SMILES

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

InChI

InChIKey=XQZVQQZZOVBNLU-QDTBLXIISA-N
InChI=1S/C18H22O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,19,21H,2-3,5,7-9H2,1H3/t11-,12-,14+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H22O3
Molecular Weight 286.3655
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11054642

4-Hydroxyestrone (4-OHE1) is a carcinogenic metabolite originating from 17beta-estradiol (17β-E2) hormone. 4-OHE1 was a partial estrogen agonist on cancellous bone turnover, similar to 17β-E2, is able to emit electrons from its excited singlet state. The quantum yield is nearly the same like this of 17β-E2 and decreases with increasing substrate concentration, but enhances with temperature. The 4-OHE1 transient derived from the electron ejection process is leading to the formation of a secondary metabolite by reaction with the present C2H4OH radical. This fact indicates, that depending on the life habits of a person, a variety of metabolites can be formed, also such initiating cancer.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Reinduction of the hypnotic effects of thiopental with NSAIDs by decreasing thiopental plasma protein binding in humans.
1993 Apr
Characterization of rabbit UDP-glucuronosyltransferase UGT1A7: tertiary amine glucuronidation is catalyzed by UGT1A7 and UGT1A4.
1997 Aug 15
Quantitative determination of 3,3'-diindolylmethane in urine of individuals receiving indole-3-carbinol.
2001
Expression of UGT2B7, a UDP-glucuronosyltransferase implicated in the metabolism of 4-hydroxyestrone and all-trans retinoic acid, in normal human breast parenchyma and in invasive and in situ breast cancers.
2002 Apr
Catecholestrogen sulfation: possible role in carcinogenesis.
2002 Mar 29
Estradiol metabolism and malignant disease.
2002 Sep 30
Detection of estrogen DNA-adducts in human breast tumor tissue and healthy tissue by combined nano LC-nano ES tandem mass spectrometry.
2003 May
Development of monoclonal antibodies to 4-hydroxyestrogen-2-N-acetylcysteine conjugates: immunoaffinity and spectroscopic studies.
2005 Oct
Role of polymorphic human cytochrome P450 enzymes in estrone oxidation.
2006 Mar
Analysis of fifteen estrogen metabolites using packed column supercritical fluid chromatography-mass spectrometry.
2006 Mar 1
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Potential biomarker for early risk assessment of prostate cancer.
2006 Oct 1
Redox cycling of catechol estrogens generating apurinic/apyrimidinic sites and 8-oxo-deoxyguanosine via reactive oxygen species differentiates equine and human estrogens.
2010 Aug 16
The normal breast microenvironment of premenopausal women differentially influences the behavior of breast cancer cells in vitro and in vivo.
2010 May 21

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:01:20 GMT 2023
Edited
by admin
on Fri Dec 15 15:01:20 GMT 2023
Record UNII
3MN57C55S2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-HYDROXYESTRONE
Common Name English
3,4-DIHYDROXY-1,3,5(10)-ESTRATRIEN-17-ONE
Systematic Name English
ESTRA-1,3,5(10)-TRIEN-17-ONE, 3,4-DIHYDROXY-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C2181
Created by admin on Fri Dec 15 15:01:20 GMT 2023 , Edited by admin on Fri Dec 15 15:01:20 GMT 2023
Code System Code Type Description
WIKIPEDIA
4-Hydroxyestrone
Created by admin on Fri Dec 15 15:01:20 GMT 2023 , Edited by admin on Fri Dec 15 15:01:20 GMT 2023
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NCI_THESAURUS
C114469
Created by admin on Fri Dec 15 15:01:20 GMT 2023 , Edited by admin on Fri Dec 15 15:01:20 GMT 2023
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FDA UNII
3MN57C55S2
Created by admin on Fri Dec 15 15:01:20 GMT 2023 , Edited by admin on Fri Dec 15 15:01:20 GMT 2023
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PUBCHEM
9971251
Created by admin on Fri Dec 15 15:01:20 GMT 2023 , Edited by admin on Fri Dec 15 15:01:20 GMT 2023
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MESH
C026418
Created by admin on Fri Dec 15 15:01:20 GMT 2023 , Edited by admin on Fri Dec 15 15:01:20 GMT 2023
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CAS
3131-23-5
Created by admin on Fri Dec 15 15:01:20 GMT 2023 , Edited by admin on Fri Dec 15 15:01:20 GMT 2023
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EPA CompTox
DTXSID00904312
Created by admin on Fri Dec 15 15:01:20 GMT 2023 , Edited by admin on Fri Dec 15 15:01:20 GMT 2023
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CHEBI
87602
Created by admin on Fri Dec 15 15:01:20 GMT 2023 , Edited by admin on Fri Dec 15 15:01:20 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY