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

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

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

Approval Year

PubMed

Title	Date	PubMed
In-vitro metabolism of [3H]testosterone by scalp and back skin: conversion of testosterone into 5alpha-androstane-3beta, 17beta-diol.	1977 Mar	856929
Proposed mechanism for sperm chromatin condensation/decondensation in the male rat.	2003 Feb 11	12646056
Testosterone modulation of seizure susceptibility is mediated by neurosteroids 3alpha-androstanediol and 17beta-estradiol.	2004	15489042
The human cytochrome P4507B1: catalytic activity studies.	2004 Dec	15698543
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 Dec 1	15458794
Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements.	2004 Jul	15370836
HPLC-RIA analysis of steroid hormone profile in a virilizing stromal tumor of the ovary.	2004 Oct 29	15560921
The androgen derivative 5alpha-androstane-3beta,17beta-diol inhibits prostate cancer cell migration through activation of the estrogen receptor beta subtype.	2005 Jun 15	15958594
17beta-estradiol induces apoptosis in the developing rodent prostate independently of ERalpha or ERbeta.	2006 Jan	16223864
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	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 Oct 6	17026757
Triphenyltin alters androgen metabolism in the sea urchin Paracentrotus lividus.	2006 Sep 12	16846652
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 Dec	17854852
CYP7B1-mediated metabolism of dehydroepiandrosterone and 5alpha-androstane-3beta,17beta-diol--potential role(s) for estrogen signaling.	2008 Apr	18331353
Androgens with activity at estrogen receptor beta have anxiolytic and cognitive-enhancing effects in male rats and mice.	2008 Nov	18775724
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 Apr 1	19286044
Assessment of metabolic capabilities of PLHC-1 and RTL-W1 fish liver cell lines.	2009 Dec	19142739
A role for the androgen metabolite, 5alpha-androstane-3beta,17beta-diol, in modulating oestrogen receptor beta-mediated regulation of hormonal stress reactivity.	2009 Mar	19207807
Epimerase activity of the human 11beta-hydroxysteroid dehydrogenase type 1 on 7-hydroxylated C19-steroids.	2009 Mar	19167490
Androgens upregulate cyp19a1b (aromatase B) gene expression in the brain of zebrafish (Danio rerio) through estrogen receptors.	2009 May	19129512
The androgen metabolite 5alpha-androstane-3beta,17beta-diol (3betaAdiol) induces breast cancer growth via estrogen receptor: implications for aromatase inhibitor resistance.	2009 May	18521740
ERbeta: recent understanding of estrogen signaling.	2010 Sep	20646931
Estrogen receptor beta and the progression of prostate cancer: role of 5alpha-androstane-3beta,17beta-diol.	2010 Sep	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 Sep	20557886

Name

Type

Language

3.BETA.-ANDROSTANEDIOL

Common 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

MAXTERONE

Brand Name

English

Classification Tree Code System Code

LOINC

9640-4