5alpha-Androstan-3beta-ol (CHEM017469)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:23:02 UTC
Update Date2016-11-09 01:15:36 UTC
Accession NumberCHEM017469
Identification
Common Name5alpha-Androstan-3beta-ol
ClassSmall Molecule
Description5a-Androstan-3b-ol is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. 5a-Androstan-3b-ol has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. 5a-Androstan-3b-ol as a pheromone is well suited because of high volatility and lipophilicity. (PMID: 1419890, 8142319, 16415088).
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
AndrostanolMeSH
5 alpha-Androstan-3 beta-olMeSH
Androstan-3-olMeSH
(3.beta.,5.alpha.)-androstan-3-olHMDB
(3b)-Androstan-3-olHMDB
(3b,5a)-Androstan-3-olHMDB
(3beta)-Androstan-3-olHMDB
(3beta,5alpha)-Androstan-3-olHMDB
3.beta.-hydroxy-5.alpha.-androstaneHMDB
3b-Hydroxy-5a-androstaneHMDB
5.alpha.-androstan-3.beta.-olHMDB
5alpha-Androstan-3beta-olHMDB
Chemical FormulaC19H32O
Average Molecular Mass276.457 g/mol
Monoisotopic Mass276.245 g/mol
CAS Registry Number1224-92-6
IUPAC Name(1S,2S,5S,7S,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol
Traditional Name5α-androstan-3β-ol
SMILES[H][C@@]12CCC[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[C@]12C
InChI IdentifierInChI=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
InChI KeyDJTOLSNIKJIDFF-LOVVWNRFSA-N
Chemical Taxonomy
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
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00024 g/LALOGPS
logP5.01ALOGPS
logP4.43ChemAxon
logS-6.1ALOGPS
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
Refractivity83.12 m³·mol⁻¹ChemAxon
Polarizability34.53 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-0190000000-5b1754ded0ac467b5f5cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00si-3249000000-3eef15d5d5028252c85dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0090000000-31d0be0d5a0033e55a93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1390000000-61479ffeec6870a87f77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gc1-4590000000-f6887a3f9a491e6f06fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-47d4322f04632b68d5b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-55606174ad85aba50949Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6v-1190000000-fb38b756d45b8098957dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-ab934a3fbfa1231bc3f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r1-1940000000-b22fa03f673568c80c7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-5900000000-ae9349931f7ad447c503Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-cd8c49651d54ec9e7264Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-cd8c49651d54ec9e7264Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-0090000000-1f168a898ca8148f62efSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0005830
FooDB IDFDB023776
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID83841
ChEBI ID428105
PubChem Compound ID92877
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Kwan TK, Trafford DJ, Makin HL, Mallet AI, Gower DB: GC-MS studies of 16-androstenes and other C19 steroids in human semen. J Steroid Biochem Mol Biol. 1992 Nov;43(6):549-56.
2. Gower DB, Holland KT, Mallet AI, Rennie PJ, Watkins WJ: Comparison of 16-androstene steroid concentrations in sterile apocrine sweat and axillary secretions: interconversions of 16-androstenes by the axillary microflora--a mechanism for axillary odour production in man? J Steroid Biochem Mol Biol. 1994 Mar;48(4):409-18.
3. Kaminski RM, Marini H, Ortinski PI, Vicini S, Rogawski MA: The pheromone androstenol (5 alpha-androst-16-en-3 alpha-ol) is a neurosteroid positive modulator of GABAA receptors. J Pharmacol Exp Ther. 2006 May;317(2):694-703. Epub 2006 Jan 13.