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
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
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
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
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
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
Reductive 17beta-hydroxysteroid dehydrogenases in the sulfatase pathway: critical in the cell proliferation of breast cancer.	2009 Mar 25	19038308
The androgen metabolite 5alpha-androstane-3beta,17beta-diol (3betaAdiol) induces breast cancer growth via estrogen receptor: implications for aromatase inhibitor resistance.	2009 May	18521740
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

Substance Class	Chemical Created by `admin` on `Wed Jul 05 22:41:13 UTC 2023` Edited by `admin` on `Wed Jul 05 22:41:13 UTC 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