1.0 2010-04-08 22:10:23 UTC 2019-11-26 03:07:41 UTC FDB012828 (3alpha,5alpha)-Androst-16-en-3-ol Aroma substance from the Perigord truffle tuber Androstenol is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. Androstenol has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. Androstenol as a pheromone is well suited because of high volatility and lipophilicity. (PMID: 1419890, 8142319, 16415088); ; 3a-Hydroxyandrost-16-ene is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. 3a-Hydroxyandrost-16-ene has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. 3a-Hydroxyandrost-16-ene is structurally similar to endogenous A-ring reduced neurosteroids that act as positive modulators of GABAA receptors. 3a-Hydroxyandrost-16-ene has neurosteroid-like activity as a GABAA receptor modulator. The various actions of 3a-Hydroxyandrost-16-ene in the whole-animal models are consistent with its activity as a GABAA receptor modulator. GABAA receptors could represent a target for 3a-Hydroxyandrost-16-ene as a pheromone, for which it is well suited because of high volatility and lipophilicity, or as a conventional hormonal neurosteroid. (PMID: 1419890, 8142319, 16415088); Androstenol is an sex pheromone in pigs, possessing a musk-like odor.; The Pheromone Androstenol (5{alpha}-Androst-16-en-3{alpha}-ol) Is a Neurosteroid Positive Modulator of GABAA Receptors -- Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA 317 (2): 694 -- Journal of Pharmacology and Experimental Therapeutics; The pheromone androstenol (5?-androst-16-en-3?-ol) is a neurosteroid positive modulator of GABAA receptors. (3a,5a)-Androst-16-en-3-ol (3alpha,5alpha)-Androst-16-en-3-ol (3alpha,5alpha)-Androst-16-en-3-ol;5a-Androst-16-en-3a-ol (3α,5α)-androst-16-en-3-ol 16-(5alpha)Androsten-3alpha-ol 16,17-Androstene-3-ol 3&alpha;-Hydroxyandrost-16-ene 3a-Hydroxy-5a-androst-16-ene 3a-Hydroxyandrost-16-ene 3a-Hydroxyandrostene 3alpha-Hydroxy-5alpha-androst-16-ene 3alpha-Hydroxyandrost-16-ene 3α-hydroxyandrost-16-ene 5&alpha;-Androst-16-en-3&alpha;-ol 5a-Androst-16-en-3a-ol 5alpha-Androst-16-en-3alpha-ol Androst-16-en-3-ol Androst-16-en-3-ol, (3&alpha;,5&alpha;)- Androst-16-en-3-ol, (3alpha,5alpha)- (9CI) Androst-16-en-3a-ol Androst-16-en-3alpha-ol Androst-16-en-3α-ol Androstenol ATE E 281;3a-Hydroxyandrost-16-ene C19H30O 274.4409 274.229665582 2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol 2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol 1153-51-1 CC12CCC3C(CCC4CC(O)CCC34C)C1CC=C2 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 KRVXMNNRSSQZJP-UHFFFAOYSA-N belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Androgens and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Androstane steroids Aliphatic homopolycyclic compounds 3-hydroxysteroids Cyclic alcohols and derivatives Hydrocarbon derivatives Secondary alcohols 3-hydroxysteroid Alcohol Aliphatic homopolycyclic compound Androgen-skeleton Cyclic alcohol Hydrocarbon derivative Hydroxysteroid Organic oxygen compound Organooxygen compound Secondary alcohol Solid logp 5.13 ALOGPS logs -5.89 ALOGPS solubility 3.55e-04 g/l ALOGPS melting_point Mp 143.5-144° logp 4.07 ChemAxon pka_strongest_acidic 18.3 ChemAxon pka_strongest_basic -1.4 ChemAxon iupac 2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol ChemAxon average_mass 274.4409 ChemAxon mono_mass 274.229665582 ChemAxon smiles CC12CCC3C(CCC4CC(O)CCC34C)C1CC=C2 ChemAxon formula C19H30O ChemAxon inchi 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 ChemAxon inchikey KRVXMNNRSSQZJP-UHFFFAOYSA-N ChemAxon polar_surface_area 20.23 ChemAxon refractivity 84.23 ChemAxon polarizability 33.81 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 105415 Specdb::CMs 117490 Specdb::CMs 128353 Specdb::CMs 129168 Specdb::MsMs 59625 Specdb::MsMs 59626 Specdb::MsMs 59627 Specdb::MsMs 115803 Specdb::MsMs 115804 Specdb::MsMs 115805 Specdb::MsMs 3408786 Specdb::MsMs 3408787 Specdb::MsMs 3408788 Specdb::MsMs 3408789 Specdb::MsMs 3408790 Specdb::MsMs 3408791 HMDB05935 40933 ATE #<Reference:0x000055ce324c9928> #<Reference:0x000055ce324c9748> #<Reference:0x000055ce324c9540> Common mushroom Type 1 specific Agaricus bisporus 5341 Mushrooms Unknown generic Oyster mushroom Type 1 specific Pleurotus ostreatus 5322 animal musk natural Nuclear receptor subfamily 1 group I member 3 Q14994 NR1I3