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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 of 3.BETA.-ANDROSTANEDIOL

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

PubMed

TitleDatePubMed
In-vitro metabolism of [3H]testosterone by scalp and back skin: conversion of testosterone into 5alpha-androstane-3beta, 17beta-diol.
1977 Mar
Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements.
2004 Jul
HPLC-RIA analysis of steroid hormone profile in a virilizing stromal tumor of the ovary.
2004 Oct 29
Metabolite ligands of estrogen receptor-beta reduce primate coronary hyperreactivity.
2006 Jan
Regulation of steroid hydroxylase CYP7B1 by androgens and estrogens in prostate cancer LNCaP cells.
2006 Jun 2
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Triphenyltin alters androgen metabolism in the sea urchin Paracentrotus lividus.
2006 Sep 12
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
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
Androgens with activity at estrogen receptor beta have anxiolytic and cognitive-enhancing effects in male rats and mice.
2008 Nov
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
Reductive 17beta-hydroxysteroid dehydrogenases in the sulfatase pathway: critical in the cell proliferation of breast cancer.
2009 Mar 25
The androgen metabolite 5alpha-androstane-3beta,17beta-diol (3betaAdiol) induces breast cancer growth via estrogen receptor: implications for aromatase inhibitor resistance.
2009 May
Measurement of sex steroids in murine blood and reproductive tissues by liquid chromatography-tandem mass spectrometry.
2010 Aug
ERbeta: recent understanding of estrogen signaling.
2010 Sep
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
  • Download
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
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
DEA NO. 4000
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
LOINC 15026-8
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
LOINC 1850-7
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
LOINC 23815-4
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
Code System Code Type Description
NSC
50891
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID8022379
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
PRIMARY
DRUG BANK
DB03882
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
PRIMARY
FDA UNII
6J0K4253QD
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
PRIMARY
ECHA (EC/EINECS)
209-334-3
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
PRIMARY
WIKIPEDIA
3β-Androstanediol
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
PRIMARY
CHEBI
18329
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
PRIMARY
CAS
571-20-0
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
PRIMARY
PUBCHEM
242332
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
PRIMARY
CHEBI
27727
Created by admin on Wed Jul 05 22:41:13 UTC 2023 , Edited by admin on Wed Jul 05 22:41:13 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
In reproductive tissues, dihydrotestosterone is further metabolized to 3-alpha and 3-beta androstanediol
PARENT -> METABOLITE
IN VITRO
Related Record Type Details
ACTIVE MOIETY