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

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
In-vitro metabolism of [3H]testosterone by scalp and back skin: conversion of testosterone into 5alpha-androstane-3beta, 17beta-diol.	1977 Mar	856929
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 Dec 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 Jun 29	11290741
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
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 Dec	15582534
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
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 Mar 12	14672942
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
Metabolite ligands of estrogen receptor-beta reduce primate coronary hyperreactivity.	2006 Jan	16199482
Regulation of steroid hydroxylase CYP7B1 by androgens and estrogens in prostate cancer LNCaP cells.	2006 Jun 2	16630558
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
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 Dec	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 Dec	17854852
Estrogen receptor-beta mediates dihydrotestosterone-induced stimulation of the arginine vasopressin promoter in neuronal cells.	2007 Jul	17412808
5Alpha-androstane-3beta,7alpha,17beta-triol and 5alpha-androstane-3beta,7beta,17beta-triol as substrates for the human 11beta-hydroxysteroid dehydrogenase type 1.	2007 Nov	17825335
Regulation and expression of human CYP7B1 in prostate: overexpression of CYP7B1 during progression of prostatic adenocarcinoma.	2007 Sep 15	17639508
CYP7B1-mediated metabolism of dehydroepiandrosterone and 5alpha-androstane-3beta,17beta-diol--potential role(s) for estrogen signaling.	2008 Apr	18331353
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 May	18067894
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
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 Dec 10	19772289
Steroid hormone transforming aldo-keto reductases and cancer.	2009 Feb	19250190
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
Reductive 17beta-hydroxysteroid dehydrogenases in the sulfatase pathway: critical in the cell proliferation of breast cancer.	2009 Mar 25	19038308
Androgens upregulate cyp19a1b (aromatase B) gene expression in the brain of zebrafish (Danio rerio) through estrogen receptors.	2009 May	19129512
MMP7 expression regulated by endocrine therapy in ERbeta-positive colon cancer cells.	2009 Sep 29	19785773
ERbeta impedes prostate cancer EMT by destabilizing HIF-1alpha and inhibiting VEGF-mediated snail nuclear localization: implications for Gleason grading.	2010 Apr 13	20385358
Measurement of sex steroids in murine blood and reproductive tissues by liquid chromatography-tandem mass spectrometry.	2010 Aug	20144714
ERbeta: recent understanding of estrogen signaling.	2010 Sep	20646931
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
Effects of CYP7B1-mediated catalysis on estrogen receptor activation.	2010 Sep	20553962

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:09:26 GMT 2023` Edited by `admin` on `Fri Dec 15 15:09:26 GMT 2023`
Record UNII	6J0K4253QD
Record Status	`Validated (UNII)`
Record Version

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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