2-HYDROXYESTRADIOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H24O3
Molecular Weight	288.3814
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=DILDHNKDVHLEQB-XSSYPUMDSA-N

InChI=1S/C18H24O3/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/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H24O3
Molecular Weight	288.3814
Charge	0
Count

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

Approval Year

PubMed

Title	Date	PubMed
Increased 2-methoxyestradiol production in human coronary versus aortic vascular cells.	2001 Feb	11230352
Effects of estradiol and its metabolites on glomerular endothelial nitric oxide synthesis and mesangial cell growth.	2001 Feb	11230350
Estradiol metabolites inhibit endothelin synthesis by an estrogen receptor-independent mechanism.	2001 Feb	11230349
Gas chromatographic determination of catecholestrogens following isolation by solid-phase extraction.	2001 Jul 15	11486823
Reduction of post injury neointima formation due to 17beta-estradiol and phytoestrogen treatment is not influenced by the pure synthetic estrogen receptor antagonist ICI 182,780 in vitro.	2002 Aug 6	12162794
Stimulatory effect of cigarette smoking on the 15 alpha-hydroxylation of estradiol by human term placenta.	2002 May	12011817
Crystal structure of human sex hormone-binding globulin in complex with 2-methoxyestradiol reveals the molecular basis for high affinity interactions with C-2 derivatives of estradiol.	2002 Nov 22	12228253
Comparison of ex vivo inhibitory effect between 2-hydroxyestradiol and its 17-sulfate on rat hepatic microsomal lipid peroxidation.	2003 Aug	14577664
Catecholamines block the antimitogenic effect of estradiol on human glomerular mesangial cells.	2003 Sep	12913061
Estradiol metabolites as isoform-specific inhibitors of human glutathione S-transferases.	2004 Dec 30	15607759
Lycopene and beta-carotene ameliorate catechol estrogen-mediated DNA damage.	2005 Feb	15822859
Effects of dioxin on metabolism of estrogens in waste incinerator workers.	2005 Jul-Aug	17214292
Specific binding of 4-hydroxyestradiol to mouse uterine protein: evidence of a physiological role for 4-hydroxyestradiol.	2005 May	15845916
Regulation of CFTR channels by HCO(3)--sensitive soluble adenylyl cyclase in human airway epithelial cells.	2005 Nov	15958523
Estradiol and its metabolites 4-hydroxyestradiol and 2-hydroxyestradiol induce mutations in human breast epithelial cells.	2006 Apr 15	16287077
Regioselective 2-hydroxylation of 17beta-estradiol by rat cytochrome P4501B1.	2006 Nov 1	16893557
Estrogens, enzyme variants, and breast cancer: a risk model.	2006 Sep	16985022
Inhibition of the human liver microsomal and human cytochrome P450 1A2 and 3A4 metabolism of estradiol by deployment-related and other chemicals.	2006 Sep	16790556

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:09:14 GMT 2023` Edited by `admin` on `Fri Dec 15 15:09:14 GMT 2023`
Record UNII	AYU2L67YUU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-HYDROXYESTRADIOL

Common Name

English

ESTRADIOL METABOLITE (2-HYDROXYESTRADIOL)

Common Name

English

NSC-61711

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C2181