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Showing Compound (3alpha,5alpha)-Androst-16-en-3-ol (FDB012828)

Record Information
Version1.0
Creation date2010-04-08 22:10:23 UTC
Update date2019-11-26 03:07:41 UTC
Primary IDFDB012828
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3alpha,5alpha)-Androst-16-en-3-ol
DescriptionAroma 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.
CAS Number1153-51-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(3a,5a)-Androst-16-en-3-olGenerator
(3Α,5α)-androst-16-en-3-olGenerator
5a-Androsta-16-ene-3-olGenerator
5Α-androsta-16-ene-3-olGenerator
(3alpha,5alpha)-Androst-16-en-3-olbiospider
(3alpha,5alpha)-Androst-16-en-3-ol;5a-Androst-16-en-3a-olbiospider
(3α,5α)-androst-16-en-3-olGenerator
16-(5alpha)Androsten-3alpha-olbiospider
16,17-Androstene-3-olbiospider
3α-Hydroxyandrost-16-enebiospider
3a-Hydroxy-5a-androst-16-enebiospider
3a-Hydroxyandrost-16-eneGenerator
3a-Hydroxyandrostenebiospider
3alpha-Hydroxy-5alpha-androst-16-enebiospider
3alpha-Hydroxyandrost-16-enebiospider
3α-hydroxyandrost-16-eneGenerator
5α-Androst-16-en-3α-olbiospider
5a-Androst-16-en-3a-olHMDB
5alpha-Androst-16-en-3alpha-olbiospider
Androst-16-en-3-olbiospider
Androst-16-en-3-ol, (3α,5α)-biospider
Androst-16-en-3-ol, (3alpha,5alpha)- (9CI)biospider
Androst-16-en-3a-olGenerator
Androst-16-en-3alpha-olbiospider
Androst-16-en-3α-olGenerator
Androstenolbiospider
ATEbiospider
E 281;3a-Hydroxyandrost-16-enebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.00036 g/LALOGPS
logP5.13ALOGPS
logP4.07ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.23 m³·mol⁻¹ChemAxon
Polarizability33.81 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H30O
IUPAC name2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol
InChI IdentifierInChI=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
InChI KeyKRVXMNNRSSQZJP-UHFFFAOYSA-N
Isomeric SMILESCC12CCC3C(CCC4CC(O)CCC34C)C1CC=C2
Average Molecular Weight274.4409
Monoisotopic Molecular Weight274.229665582
Classification
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 83.15%; H 11.02%; O 5.83%DFC
Melting PointMp 143.5-144°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +15 (c, 1.33 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(3alpha,5alpha)-Androst-16-en-3-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052b-0190000000-13328b1f40964b0accdcSpectrum
Predicted GC-MS(3alpha,5alpha)-Androst-16-en-3-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5alpha)-Androst-16-en-3-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5alpha)-Androst-16-en-3-ol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0090000000-1be7cd81baa4d84a37892016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1390000000-ed025605b018708efcde2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mk-4590000000-855def90dad1c5c1e9512016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-1541ebdd0dbc2495323f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-0ac5caa5bbe92d84a24d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1190000000-cff2612a42b766eff16e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-8a564be2c0b3f79774ef2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1790000000-6a6baaf9b8c5d7717e452021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0535-9700000000-f613b5811b9167d439e42021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-c0274c5a0ec76c02edd62021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-c0274c5a0ec76c02edd62021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0090000000-596a71488841027ba40b2021-10-12View Spectrum
NMRNot Available
ChemSpider ID92136
ChEMBL IDCHEMBL142348
KEGG Compound IDNot Available
Pubchem Compound ID101989
Pubchem Substance IDNot Available
ChEBI ID40933
Phenol-Explorer IDNot Available
DrugBank IDDB01889
HMDB IDHMDB05935
CRC / DFC (Dictionary of Food Compounds) IDHMB64-D:HMB65-E
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDATE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1010781
SuperScent IDNot Available
Wikipedia IDAndrostenol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Nuclear receptor subfamily 1 group I member 3NR1I3Q14994
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
animal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
musk
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
natural
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference