(3alpha,5alpha)-Androst-16-en-3-ol (CHEM028477)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:29:15 UTC
Update Date2016-11-09 01:18:42 UTC
Accession NumberCHEM028477
Identification
Common Name(3alpha,5alpha)-Androst-16-en-3-ol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3alpha,5alpha)-Androst-16-en-3-olChEBI
3alpha-Hydroxyandrost-16-eneChEBI
Androst-16-en-3alpha-olChEBI
(3a,5a)-Androst-16-en-3-olGenerator
(3Α,5α)-androst-16-en-3-olGenerator
3a-Hydroxyandrost-16-eneGenerator
3Α-hydroxyandrost-16-eneGenerator
Androst-16-en-3a-olGenerator
Androst-16-en-3α-olGenerator
16,17-Androstene-3-olHMDB
3a-Hydroxy-5a-androst-16-eneHMDB
3a-HydroxyandrosteneHMDB
5a-Androst-16-en-3a-olHMDB
5alpha-Androst-16-en-3alpha-olHMDB
Androst-16-en-3-olHMDB
5 alpha-Androst-16-en-3 alpha-olHMDB
Androst-16-en-3 alpha-olHMDB
a-AndrostenolHMDB
Α-androstenolHMDB
AndrostenolChEBI
Chemical FormulaC19H30O
Average Molecular Mass274.441 g/mol
Monoisotopic Mass274.230 g/mol
CAS Registry Number1153-51-1
IUPAC Name(1S,2S,5R,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol
Traditional Name(1S,2S,5R,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol
SMILESCC12CCC3C(CCC4CC(O)CCC34C)C1CC=C2
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
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-alpha-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 Solubility0.00036 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
Polarizability33.67 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, Positivesplash10-05mk-1190000000-2998cb0396687c8b9897Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0159-4249000000-8c4afa438fe5fff4e717Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0090000000-1be7cd81baa4d84a3789Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1390000000-ed025605b018708efcdeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mk-4590000000-855def90dad1c5c1e951Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-1541ebdd0dbc2495323fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-0ac5caa5bbe92d84a24dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-1190000000-cff2612a42b766eff16eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-312b5e8b6401fa650e17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00mk-1930000000-e0db6359d078ed97578fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-6900000000-f1d874e55c03f8da2828Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-c0274c5a0ec76c02edd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-c0274c5a0ec76c02edd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0090000000-b42c05dd2b34d249babaSpectrum
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 IDDB01889
HMDB IDHMDB0005935
FooDB IDFDB112227
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDATE
Wikipedia LinkAndrostenol
Chemspider ID92136
ChEBI ID40933
PubChem Compound ID101989
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.