2-HYDROXYESTRONE

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 Search

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(O)=C(O)C=C34)[C@@H]1CCC2=O

InChI

InChIKey=SWINWPBPEKHUOD-JPVZDGGYSA-N

InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/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

Approval Year

PubMed

Title	Date	PubMed
Urinary estrogen metabolites in women at high risk for breast cancer.	2009-09	19502596
Ethnicity, body size, and estrogen levels in postmenopausal Hispanic and non-Hispanic white women.	2009-04	19361315
Lycium barbarum inhibits growth of estrogen receptor positive human breast cancer cells by favorably altering estradiol metabolism.	2009	19373615
A liquid chromatography-mass spectrometry method for the simultaneous measurement of 15 urinary estrogens and estrogen metabolites: assay reproducibility and interindividual variability.	2008-12	19064556
Daidzein-metabolizing phenotypes in relation to serum hormones and sex hormone binding globulin, and urinary estrogen metabolites in premenopausal women in the United States.	2008-12	18478336
Hydroxylated estrogen metabolites influence the proliferation of cultured human monocytes: possible role in synovial tissue hyperplasia.	2008-11-27	19032826
Coffee intake and CYP1A2*1F genotype predict breast volume in young women: implications for breast cancer.	2008-11-04	18813311
Fat/fiber intakes and sex hormones in healthy premenopausal women in USA.	2008-11	18761407
Levels of sex steroid and cardiovascular disease measures in premenopausal and hormone-treated women at midlife: implications for the "timing hypothesis".	2008-10-27	18955645
Past oral contraceptive use and current dietary soy isoflavones influence estrogen metabolism in postmenopausal monkeys (Macaca fascicularis).	2008-10	18843000
Contribution of alpha2-adrenoceptors to the mitogenic effect of catecholestrogen in human breast cancer MCF-7 cells.	2008-05	18486470
Oestrogen metabolites in relation to isoprostanes as a measure of oxidative stress.	2008-05	17980014
Phytoestrogens and breast cancer prevention: possible mechanisms of action.	2008-04	18414622
Coffee consumption and CYP1A2*1F genotype modify age at breast cancer diagnosis and estrogen receptor status.	2008-04	18398030
The influence of menstrual risk factors on tumor characteristics and survival in postmenopausal breast cancer.	2008	19087323
Treatment with an inhibitor of catechol-O-methyltransferase activity reduces preterm birth and impedes cervical resistance to stretch in pregnant rats.	2007-12	18042640
Development of a nanomechanical biosensor for analysis of endocrine disrupting chemicals.	2007-09	17713618
HPLC for stress-free screening of potential prostate cancer marker catechol estrogens in urine using a diamond-electrode electrochemical and a fluorescence detector.	2007-09	17668912
A pilot and feasibility study on the effects of naturopathic botanical and dietary interventions on sex steroid hormone metabolism in premenopausal women.	2007-08	17684134
The effects of soygerm extracts on blood lipoproteins, antioxidative capacity and urinary estrogen metabolites in postmenopausal women on hormone therapy.	2007-07	17467711
Soy isoflavone intake and estrogen excretion patterns in young women: effect of probiotic administration.	2007-06-27	17591361
Effects of aerobic exercise training on estrogen metabolism in premenopausal women: a randomized controlled trial.	2007-04	17416764
Estrogen metabolism modulates bone density in men.	2007-04	17406768
Soy isoflavonoid effects on endogenous estrogen metabolism in postmenopausal female monkeys.	2007-04	17032659
Changes in 2-hydroxyestrone and 16alpha-hydroxyestrone metabolism with flaxseed consumption: modification by COMT and CYP1B1 genotype.	2007-02	17301257
Urinary phytoestrogen excretion of rats bearing methylnitrosourea-induced mammary carcinoma in response to treatment with 2-methoxyestradiol.	2007-02	17081745
Effects of dioxin on metabolism of estrogens in waste incinerator workers.	2007-01-12	17214292
Analysis of change.	2007	18450054
Moderate coffee and alcohol consumption improves the estrogen metabolite profile in adjuvant treated breast cancer patients: a pilot study comparing pre- and post-operative levels.	2006-12	16978896
CYP1A1 and CYP1B1 polymorphisms and their association with estradiol and estrogen metabolites in women who are premenopausal and perimenopausal.	2006-09	16949388
Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor alpha and beta subtypes: Insights into the structural determinants favoring a differential subtype binding.	2006-09	16728493
Estradiol and its metabolites and their association with knee osteoarthritis.	2006-08	16871545
A hormonal association between estrogen metabolism and proliferative thyroid disease.	2006-06	16730526
Selected diet and lifestyle factors are associated with estrogen metabolites in a multiracial/ethnic population of women.	2006-06	16702326
A randomized phase II trial of indole-3-carbinol in the treatment of vulvar intraepithelial neoplasia.	2006-05-10	16681761
Analysis of fifteen estrogen metabolites using packed column supercritical fluid chromatography-mass spectrometry.	2006-03-01	16503607
Role of polymorphic human cytochrome P450 enzymes in estrone oxidation.	2006-03	16537715
Estrogen metabolites and systolic blood pressure in a population-based sample of postmenopausal women.	2006-03	16384842
Effects of docosahexaenoic acid supplementation on blood lipids, estrogen metabolism, and in vivo oxidative stress in postmenopausal vegetarian women.	2006-03	16278686
Comparison of plasma and urinary levels of 2-hydroxyestrogen and 16 alpha-hydroxyestrogen metabolites.	2006-02	16165383
Multilocus analysis of SNP and metabolic data within a given pathway.	2006-01-13	16412218
Estrogen metabolism and breast cancer.	2006-01	16357599
Measuring fifteen endogenous estrogens simultaneously in human urine by high-performance liquid chromatography-mass spectrometry.	2005-10-15	16223252
Clinical effects of a proprietary combination isoflavone nutritional supplement in menopausal women: a pilot trial.	2005-09-30	16189949
The relationship between physical activity and 2-hydroxyestrone, 16alpha-hydroxyestrone, and the 2/16 ratio in premenopausal women (United States).	2005-05	15953988
Associations between aerobic fitness and estrogen metabolites in premenopausal women.	2005-04	15809556
Urinary estrogen metabolites, prostate specific antigen, and body mass index among African-American men in South Carolina.	2005	16289388
Androgen conversion in osteoarthritis and rheumatoid arthritis synoviocytes--androstenedione and testosterone inhibit estrogen formation and favor production of more potent 5alpha-reduced androgens.	2005	16207335
A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio.	2005	16207128
CYP17 5'-UTR MspA1 polymorphism and the risk of premenopausal breast cancer in a German population-based case-control study.	2005	15987450

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:48:17 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:17 GMT 2025`
Record UNII	UQS3A06ILY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CATECHOLESTRONE

Preferred Name

English

2-HYDROXYESTRONE

Common Name

English

ESTRA-1,3,5(1)-TRIEN-17-ONE, 2,3-DIHYDROXY-

Common Name

English

2,3-DIHYDROXYESTRA-1,3,5(10)-TRIEN-17-ONE

Systematic Name

English

Classification Tree Code System Code

LOINC

49827-9