ANDROSTENOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H30O
Molecular Weight	274.4409
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=KRVXMNNRSSQZJP-PHFHYRSDSA-N

InChI=1S/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H30O
Molecular Weight	274.4409
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/16415088 | https://www.ncbi.nlm.nih.gov/pubmed/20174662

Androstenol (5α-androst-16-en-3α-ol), a pheromone that acts as a potent positive allosteric modulator of the GABA-A receptor. Androstenol was first isolated from boar testes, and several animal experiments suggest that androstenol is capable of reducing anxiety, as well as hippocampal epileptogenic activity. It was subsequently detected in humans, (primarily in males), in sweat, urine, plasma, and saliva. Androstenol is also shown to affect hormonal, behavioral and social responses in humans. In animals, androstenol has been found to produce anxiolytic-like, antidepressant-like and anticonvulsant effects.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16415088	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Androstane metabolites bind to and deactivate the nuclear receptor CAR-beta.	1998 Oct 8	9783588
The role of 5alpha-reduction in steroid hormone physiology.	2001	11999320
Comparative biosynthetic pathway of androstenol and androgens.	2001 Jun	11457660
Calcium channel modulators of the dihydropyridine family are human pregnane X receptor activators and inducers of CYP3A, CYP2B, and CYP2C in human hepatocytes.	2001 Oct	11560876
Boar pheromone androstenol may affect the ovarian morphology in cycling gilts by humoral pathway.	2002	12056622
Specific and overlapping functions of the nuclear hormone receptors CAR and PXR in xenobiotic response.	2002	12049174
Androgen physiology: unsolved problems at the millennium.	2002 Dec 30	12573808
Boar salivary lipocalin. Three-dimensional X-ray structure and androsterol/androstenone docking simulations.	2002 May	12027882
Psychological effects of musky compounds: comparison of androstadienone with androstenol and muscone.	2002 Nov	12460587
Inhibitory cross-talk between estrogen receptor (ER) and constitutively activated androstane receptor (CAR). CAR inhibits ER-mediated signaling pathway by squelching p160 coactivators.	2002 Sep 13	12114525
Identification of constitutive androstane receptor and glucocorticoid receptor binding sites in the CYP2C19 promoter.	2003 Aug	12869636
Dual action of oestrogens on the mouse constitutive androstane receptor.	2003 Dec 1	12948398
Sex difference in the proliferative response of mouse hepatocytes to treatment with the CAR ligand, TCPOBOP.	2003 Jun	12807759
Assessment of porcine and human 16-ene-synthase, a third activity of P450c17, in the formation of an androstenol precursor. Role of recombinant cytochrome b5 and P450 reductase.	2003 Mar	12631293
Intramuscular injections of male pheromone 5 alpha-androstenol change the secretory ovarian function in gilts during sexual maturation.	2003 Nov	14688824
Molecular determinants of steroid inhibition for the mouse constitutive androstane receptor.	2003 Oct 23	14561088
Structure of the murine constitutive androstane receptor complexed to androstenol: a molecular basis for inverse agonism.	2004 Dec 22	15610734
Sterol-derived hormone(s) controls entry into diapause in Caenorhabditis elegans by consecutive activation of DAF-12 and DAF-16.	2004 Oct	15383841
The influence of male pheromones on the contractile reactivity of the isolated superficial veins of the nose and face during the estrous cycle in gilts.	2005	15794475
CAR, the continuously advancing receptor, in drug metabolism and disease.	2005 Aug	16101572
Crystallographic analysis of murine constitutive androstane receptor ligand-binding domain complexed with 5alpha-androst-16-en-3alpha-ol.	2005 Jan 1	16508121
Olfactory responsiveness to two odorous steroids in three species of nonhuman primates.	2005 Jul	15961521
Urinary marker of oral pregnenolone administration.	2005 Mar	15763596
Evolutionary selection across the nuclear hormone receptor superfamily with a focus on the NR1I subfamily (vitamin D, pregnane X, and constitutive androstane receptors).	2005 Sep 30	16197547
The influence of boar pheromones on the vasoreactivity of the facial superficial veins in ovariectomized and estradiol-treated pubertal gilts.	2006	17203739
The influence of boar pheromones on the contractile reactivity of the isolated superficial veins of the nose and face in ovariectomized prepubertal gilts and in gilts during sexual maturation.	2006	16780180
The pheromone androstenol (5 alpha-androst-16-en-3 alpha-ol) is a neurosteroid positive modulator of GABAA receptors.	2006 May	16415088
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
Induction of nuclear translocation of constitutive androstane receptor by peroxisome proliferator-activated receptor alpha synthetic ligands in mouse liver.	2007 Dec 14	17962186
Evolution of pharmacologic specificity in the pregnane X receptor.	2008 Apr 2	18384689
Detection and classification of human body odor using an electronic nose.	2009	22399995
Behavioral changes of patients after orthognathic surgery develop on the basis of the loss of vomeronasal organ: a hypothesis.	2009 Jan 22	19161592
Chemosensory cues to conspecific emotional stress activate amygdala in humans.	2009 Jul 29	19641623
A consecutive three alanine residue insertion mutant of human CAR: a novel CAR ligand screening system in HepG2 cells.	2010 Aug	20686338
Human olfaction: a constant state of change-blindness.	2010 Aug	20603708
oxLDL-induced decrease in lipid order of membrane domains is inversely correlated with endothelial stiffness and network formation.	2010 Aug	20410437
Androstenol--a steroid derived odor activates the hypothalamus in women.	2010 Feb 17	20174662
Endosulfan induces CYP2B6 and CYP3A4 by activating the pregnane X receptor.	2010 Jun 15	20361990
Protein evolution by molecular tinkering: diversification of the nuclear receptor superfamily from a ligand-dependent ancestor.	2010 Oct 5	20957188
The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species.	2011 Feb 3	21291553

Patents

Sample Use Guides

In Vivo Use Guide

in mice: systemic administration of androstenol (30-50 mg/kg) caused anxiolytic-like effects in mice in the open-field test and elevated zero-maze and antidepressant-like effects in the forced swim test (5-10 mg/kg).

Route of Administration: Intraperitoneal

In Vitro Use Guide

In whole-cell recordings from cerebellar granule cells, androstenol caused a concentration-dependent enhancement of GABA-activated currents (EC(50), 0.4 microM in cultures; 1.4 microM in slices) and prolonged the duration of spontaneous and miniature inhibitory postsynaptic currents. Androstenol (0.1-1 microM) also potentiated the amplitude of GABA-activated currents in human embryonic kidney 293 cells transfected with recombinant alpha1beta2gamma2 and alpha2beta2gamma2 GABA(A) receptors and, at high concentrations (10-300 microM), directly activated currents in these cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:32:43 GMT 2023` Edited by `admin` on `Fri Dec 15 18:32:43 GMT 2023`
Record UNII	48K9VAM062
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANDROSTENOL

Systematic Name

English

3.ALPHA.-HYDROXY-5.ALPHA.-ANDROST-16-ENE

Systematic Name

English

5.ALPHA.-ANDROST-16-EN-3.ALPHA.-OL

Systematic Name

English

NSC-71076

Code

English

(3.ALPHA.,5.ALPHA.)-ANDROST-16-EN-3-OL [MI]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

126510