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
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
| 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
| 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 |
|
| 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
Edited
Sat Jun 26 15:11:58 UTC 2021
by
admin
on
Sat Jun 26 15:11:58 UTC 2021
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| Record UNII |
6J0K4253QD
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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LOINC |
9640-4
Created by
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DEA NO. |
4000
Created by
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LOINC |
15026-8
Created by
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LOINC |
1850-7
Created by
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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
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| Code System | Code | Type | Description | ||
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571-20-0
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DB03882
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6J0K4253QD
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PRIMARY | |||
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209-334-3
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571-20-0
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PRIMARY | |||
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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
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PARENT -> METABOLITE |
IN VITRO
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PARENT -> METABOLITE |
In reproductive tissues, dihydrotestosterone is further metabolized to 3-alpha and 3-beta androstanediol
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
