3.BETA.-ANDROSTANEDIOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H32O2
Molecular Weight	292.4562
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@@H](O)CC[C@]34C)[C@@H]1CC[C@@H]2O

InChI

InChIKey=CBMYJHIOYJEBSB-YSZCXEEOSA-N

InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,17-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H32O2
Molecular Weight	292.4562
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
ERbeta: recent understanding of estrogen signaling.	2010-09	20646931
Estrogen receptor beta and the progression of prostate cancer: role of 5alpha-androstane-3beta,17beta-diol.	2010-09	20562232
The androgen derivative 5alpha-androstane-3beta,17beta-diol inhibits tumor necrosis factor alpha and lipopolysaccharide induced inflammatory response in human endothelial cells and in mice aorta.	2010-09	20557886
Effects of CYP7B1-mediated catalysis on estrogen receptor activation.	2010-09	20553962
Measurement of sex steroids in murine blood and reproductive tissues by liquid chromatography-tandem mass spectrometry.	2010-08	20144714
ERbeta impedes prostate cancer EMT by destabilizing HIF-1alpha and inhibiting VEGF-mediated snail nuclear localization: implications for Gleason grading.	2010-04-13	20385358
Potent and selective steroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 7, an enzyme that catalyzes the reduction of the key hormones estrone and dihydrotestosterone.	2009-12-10	19772289
Assessment of metabolic capabilities of PLHC-1 and RTL-W1 fish liver cell lines.	2009-12	19142739
MMP7 expression regulated by endocrine therapy in ERbeta-positive colon cancer cells.	2009-09-29	19785773
Androgens upregulate cyp19a1b (aromatase B) gene expression in the brain of zebrafish (Danio rerio) through estrogen receptors.	2009-05	19129512
The androgen metabolite 5alpha-androstane-3beta,17beta-diol (3betaAdiol) induces breast cancer growth via estrogen receptor: implications for aromatase inhibitor resistance.	2009-05	18521740
Detection of anabolic steroids in dietary supplements: the added value of an androgen yeast bioassay in parallel with a liquid chromatography-tandem mass spectrometry screening method.	2009-04-01	19286044
Reductive 17beta-hydroxysteroid dehydrogenases in the sulfatase pathway: critical in the cell proliferation of breast cancer.	2009-03-25	19038308
A role for the androgen metabolite, 5alpha-androstane-3beta,17beta-diol, in modulating oestrogen receptor beta-mediated regulation of hormonal stress reactivity.	2009-03	19207807
Epimerase activity of the human 11beta-hydroxysteroid dehydrogenase type 1 on 7-hydroxylated C19-steroids.	2009-03	19167490
Steroid hormone transforming aldo-keto reductases and cancer.	2009-02	19250190
Androgens with activity at estrogen receptor beta have anxiolytic and cognitive-enhancing effects in male rats and mice.	2008-11	18775724
An alternate pathway for androgen regulation of brain function: activation of estrogen receptor beta by the metabolite of dihydrotestosterone, 5alpha-androstane-3beta,17beta-diol.	2008-05	18067894
CYP7B1-mediated metabolism of dehydroepiandrosterone and 5alpha-androstane-3beta,17beta-diol--potential role(s) for estrogen signaling.	2008-04	18331353
Estrogen sensitivity of target genes and expression of nuclear receptor co-regulators in rat prostate after pre- and postnatal exposure to the ultraviolet filter 4-methylbenzylidene camphor.	2007-12	18174949
5alpha-Androstane-3beta,17beta-diol (3beta-diol), an estrogenic metabolite of 5alpha-dihydrotestosterone, is a potent modulator of estrogen receptor ERbeta expression in the ventral prostrate of adult rats.	2007-12	17854852
5Alpha-androstane-3beta,7alpha,17beta-triol and 5alpha-androstane-3beta,7beta,17beta-triol as substrates for the human 11beta-hydroxysteroid dehydrogenase type 1.	2007-11	17825335
Regulation and expression of human CYP7B1 in prostate: overexpression of CYP7B1 during progression of prostatic adenocarcinoma.	2007-09-15	17639508
Estrogen receptor-beta mediates dihydrotestosterone-induced stimulation of the arginine vasopressin promoter in neuronal cells.	2007-07	17412808
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Effects of 3-beta-diol, an androgen metabolite with intrinsic estrogen-like effects, in modulating the aquaporin-9 expression in the rat efferent ductules.	2006-10-06	17026757
Triphenyltin alters androgen metabolism in the sea urchin Paracentrotus lividus.	2006-09-12	16846652
Regulation of steroid hydroxylase CYP7B1 by androgens and estrogens in prostate cancer LNCaP cells.	2006-06-02	16630558
17beta-estradiol induces apoptosis in the developing rodent prostate independently of ERalpha or ERbeta.	2006-01	16223864
Metabolite ligands of estrogen receptor-beta reduce primate coronary hyperreactivity.	2006-01	16199482
The androgen derivative 5alpha-androstane-3beta,17beta-diol inhibits prostate cancer cell migration through activation of the estrogen receptor beta subtype.	2005-06-15	15958594
Endocrine active compounds affect thyrotropin and thyroid hormone levels in serum as well as endpoints of thyroid hormone action in liver, heart and kidney.	2004-12-01	15458794
The human cytochrome P4507B1: catalytic activity studies.	2004-12	15698543
Characterization of a monoclonal antibody for human aldo-keto reductase AKR1C3 (type 2 3alpha-hydroxysteroid dehydrogenase/type 5 17beta-hydroxysteroid dehydrogenase); immunohistochemical detection in breast and prostate.	2004-12	15582534
HPLC-RIA analysis of steroid hormone profile in a virilizing stromal tumor of the ovary.	2004-10-29	15560921
Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements.	2004-07	15370836
Human cytosolic 3alpha-hydroxysteroid dehydrogenases of the aldo-keto reductase superfamily display significant 3beta-hydroxysteroid dehydrogenase activity: implications for steroid hormone metabolism and action.	2004-03-12	14672942
Testosterone modulation of seizure susceptibility is mediated by neurosteroids 3alpha-androstanediol and 17beta-estradiol.	2004	15489042
Proposed mechanism for sperm chromatin condensation/decondensation in the male rat.	2003-02-11	12646056
Photoaffinity labeling of human sex hormone-binding globulin using 17alpha-alkylamine derivatives of 3beta-androstanediol substituted with azidonitrophenylamido, azidonitrophenylamino, or trifluoroazidonitrophenylamino chromophores. Localization of Trp-84 in the vicinity of the steroid-binding site.	2001-12-18	11735427
Neurosteroid hydroxylase CYP7B: vivid reporter activity in dentate gyrus of gene-targeted mice and abolition of a widespread pathway of steroid and oxysterol hydroxylation.	2001-06-29	11290741
In-vitro metabolism of [3H]testosterone by scalp and back skin: conversion of testosterone into 5alpha-androstane-3beta, 17beta-diol.	1977-03	856929

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:48:25 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:25 GMT 2025`
Record UNII	6J0K4253QD
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

3.BETA.-ANDROSTANEDIOL

Common Name

English

MAXTERONE

Preferred Name

English

NSC-50891

Code

English

5.ALPHA.-ANDROSTANE-3.BETA.,17.BETA.-DIOL

Systematic Name

English

3BETA,17BETA-DIHYDROXY-5ALPHA-ANDROSTANE

Systematic Name

English

3.BETA.,17.BETA.-ANDROSTANEDIOL

Common Name

English

3.BETA.-ADIOL

Common Name

English

ANDROSTANE-3,17-DIOL, (3.BETA.,5.ALPHA.,17.BETA.)-

Systematic Name

English

3.BETA.,17.BETA.-DIHYDROXY-5.ALPHA.-ANDROSTANE

Systematic Name

English

Classification Tree Code System Code

LOINC

9640-4