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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H32O2
Molecular Weight 292.4569
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3.BETA.-ANDROSTANEDIOL

SMILES

C[C@@]12CC[C@@]([H])(C[C@]2([H])CC[C@@]3([H])[C@]4([H])CC[C@@]([H])([C@@]4(C)CC[C@@]31[H])O)O

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 292.4569
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
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
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
Proposed mechanism for sperm chromatin condensation/decondensation in the male rat.
2003 Feb 11
Testosterone modulation of seizure susceptibility is mediated by neurosteroids 3alpha-androstanediol and 17beta-estradiol.
2004
The human cytochrome P4507B1: catalytic activity studies.
2004 Dec
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
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
Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements.
2004 Jul
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
HPLC-RIA analysis of steroid hormone profile in a virilizing stromal tumor of the ovary.
2004 Oct 29
The androgen derivative 5alpha-androstane-3beta,17beta-diol inhibits prostate cancer cell migration through activation of the estrogen receptor beta subtype.
2005 Jun 15
17beta-estradiol induces apoptosis in the developing rodent prostate independently of ERalpha or ERbeta.
2006 Jan
Metabolite ligands of estrogen receptor-beta reduce primate coronary hyperreactivity.
2006 Jan
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
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
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
Estrogen receptor-beta mediates dihydrotestosterone-induced stimulation of the arginine vasopressin promoter in neuronal cells.
2007 Jul
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
Regulation and expression of human CYP7B1 in prostate: overexpression of CYP7B1 during progression of prostatic adenocarcinoma.
2007 Sep 15
Assessment of metabolic capabilities of PLHC-1 and RTL-W1 fish liver cell lines.
2009 Dec
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
Steroid hormone transforming aldo-keto reductases and cancer.
2009 Feb
The androgen metabolite 5alpha-androstane-3beta,17beta-diol (3betaAdiol) induces breast cancer growth via estrogen receptor: implications for aromatase inhibitor resistance.
2009 May
MMP7 expression regulated by endocrine therapy in ERbeta-positive colon cancer cells.
2009 Sep 29
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
Estrogen receptor beta and the progression of prostate cancer: role of 5alpha-androstane-3beta,17beta-diol.
2010 Sep
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
Effects of CYP7B1-mediated catalysis on estrogen receptor activation.
2010 Sep
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:11:58 UTC 2021
Edited
by admin
on Sat Jun 26 15:11:58 UTC 2021
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 Sat Jun 26 15:11:58 UTC 2021 , Edited by admin on Sat Jun 26 15:11:58 UTC 2021
DEA NO. 4000
Created by admin on Sat Jun 26 15:11:58 UTC 2021 , Edited by admin on Sat Jun 26 15:11:58 UTC 2021
LOINC 15026-8
Created by admin on Sat Jun 26 15:11:58 UTC 2021 , Edited by admin on Sat Jun 26 15:11:58 UTC 2021
LOINC 1850-7
Created by admin on Sat Jun 26 15:11:58 UTC 2021 , Edited by admin on Sat Jun 26 15:11:58 UTC 2021
LOINC 23815-4
Created by admin on Sat Jun 26 15:11:58 UTC 2021 , Edited by admin on Sat Jun 26 15:11:58 UTC 2021
Code System Code Type Description
EPA CompTox
571-20-0
Created by admin on Sat Jun 26 15:11:58 UTC 2021 , Edited by admin on Sat Jun 26 15:11:58 UTC 2021
PRIMARY
DRUG BANK
DB03882
Created by admin on Sat Jun 26 15:11:58 UTC 2021 , Edited by admin on Sat Jun 26 15:11:58 UTC 2021
PRIMARY
FDA UNII
6J0K4253QD
Created by admin on Sat Jun 26 15:11:58 UTC 2021 , Edited by admin on Sat Jun 26 15:11:58 UTC 2021
PRIMARY
ECHA (EC/EINECS)
209-334-3
Created by admin on Sat Jun 26 15:11:58 UTC 2021 , Edited by admin on Sat Jun 26 15:11:58 UTC 2021
PRIMARY
CAS
571-20-0
Created by admin on Sat Jun 26 15:11:58 UTC 2021 , Edited by admin on Sat Jun 26 15:11:58 UTC 2021
PRIMARY
PUBCHEM
242332
Created by admin on Sat Jun 26 15:11:58 UTC 2021 , Edited by admin on Sat Jun 26 15:11:58 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
IN VITRO
PARENT -> METABOLITE
In reproductive tissues, dihydrotestosterone is further metabolized to 3-alpha and 3-beta androstanediol
Related Record Type Details
ACTIVE MOIETY