ANDROSTANOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H32O
Molecular Weight	276.4568
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCC[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])C[C@@H](O)CC[C@]34C

InChI

InChIKey=DJTOLSNIKJIDFF-LOVVWNRFSA-N

InChI=1S/C19H32O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h13-17,20H,3-12H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H32O
Molecular Weight	276.4568
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18832183 | https://www.ncbi.nlm.nih.gov/pubmed/9783588 | https://www.ncbi.nlm.nih.gov/pubmed/10748001 | https://www.ncbi.nlm.nih.gov/pubmed/12376703 | https://www.ncbi.nlm.nih.gov/pubmed/16273607

Androstanol is a steroid acting as the inverse agonist of constitutive androstane receptor. In addition, androstanol activates pregnane X receptor. In animal models, it protects from drug-induced liver injury. Androstanol appears to be a pheromone.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Constitutive androstane receptor 2 Target ID: CHEMBL3069 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18832183 \| https://www.ncbi.nlm.nih.gov/pubmed/9783588 \| https://www.ncbi.nlm.nih.gov/pubmed/10748001	Inverse Agonist 80	2.531 µM [EC50]
Pregnane X receptor 35 Target ID: CHEMBL3401 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10748001	Activator 1430
Nuclear receptor subfamily 1 group I member 3 4 Target ID: CHEMBL5503 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10748001 \| https://www.ncbi.nlm.nih.gov/pubmed/17585873	Inverse Agonist 80

Conditions

Condition	Modality	Targets	Highest Phase	Product
Drug-induced liver injury 10 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12376703 https://www.ncbi.nlm.nih.gov/pubmed/16273607	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Modulation of acetaminophen-induced hepatotoxicity by the xenobiotic receptor CAR.	2002 Oct 11	12376703
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.	2003 Oct	14565775
Antagonist- and inverse agonist-driven interactions of the vitamin D receptor and the constitutive androstane receptor with corepressor protein.	2005 Sep	15905360
Constitutive androstane receptor (CAR) as a potential sensing biomarker of persistent organic pollutants (POPs) in aquatic mammal: molecular characterization, expression level, and ligand profiling in Baikal seal (Pusa sibirica).	2006 Nov	16929008
The environmental estrogen, nonylphenol, activates the constitutive androstane receptor.	2007 Aug	17483497
A concentration addition model for the activation of the constitutive androstane receptor by xenobiotic mixtures.	2009 Jan	18832183
Multi-species analyses of direct activators of the constitutive androstane receptor.	2011 Oct	21778469
Quantitative analysis of the interaction of constitutive androstane receptor with chemicals and steroid receptor coactivator 1 using surface plasmon resonance biosensor systems: a case study of the Baikal seal (Pusa sibirica) and the mouse.	2013 Jan	23015691
Bile acid homeostasis controls CAR signaling pathways in mouse testis through FXRalpha.	2017 Feb 9	28181583

Patents

Sample Use Guides

In Vivo Use Guide

mice: 100 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:49:21 GMT 2023` Edited by `admin` on `Sat Dec 16 05:49:21 GMT 2023`
Record UNII	1394KPE67H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANDROSTANOL

Systematic Name

English

ANDROSTAN-3-OL

Systematic Name

English

5.ALPHA.-ANDROSTAN-3.BETA.-OL

Systematic Name

English

NSC-50887

Code

English

3.BETA.-HYDROXY-5.ALPHA.-ANDROSTANE

Systematic Name

English

ANDROSTAN-3-OL, (3.BETA.,5.ALPHA.)-

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

214-952-1