4-Androstenediol (CHEM036004)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:09:06 UTC
Update Date2016-11-09 01:21:25 UTC
Accession NumberCHEM036004
Identification
Common Name4-Androstenediol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Androst-4-ene-3beta,17beta-diolKegg
Androst-4-ene-3b,17b-diolGenerator
Androst-4-ene-3β,17β-diolGenerator
(3b,17b)-Androst-4-ene-3,17-diolHMDB
3b,17b-Dihydroxy-4-androsteneHMDB
4-Androstene-3b,17b-diolHMDB
Androst-4-en-3b,17b-diolHMDB
D4-Androstene-3b,17b-diolHMDB
(3beta,17beta)-Androst-4-ene-3,17-diolHMDB
(3β,17β)-Androst-4-ene-3,17-diolHMDB
3beta,17beta-Dihydroxy-4-androsteneHMDB
3β,17β-Dihydroxy-4-androsteneHMDB
4-AndrostenediolHMDB
Chemical FormulaC19H30O2
Average Molecular Mass290.440 g/mol
Monoisotopic Mass290.225 g/mol
CAS Registry Number1156-92-9
IUPAC Name(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol
Traditional Name(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol
SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@@H](O)CC[C@]12C
InChI IdentifierInChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyBTTWKVFKBPAFDK-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
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-4-steroid
  • Delta-4-steroid
  • 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 Solubility0.048 g/LALOGPS
logP3.1ALOGPS
logP2.95ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)17.5ChemAxon
pKa (Strongest Basic)-0.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.33 m³·mol⁻¹ChemAxon
Polarizability34.38 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-0290000000-7d52fa98e687764c22a2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-066r-3236900000-b524811a4353b5996ed1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0090000000-f4b512d07e8fa29cf8beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0290000000-7a460a768fecd3e1cea3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01oy-3890000000-8177324a0ce9fde3f678Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-7318adfbaee2ca1f4eefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0090000000-ea1dd5bd96f621180cc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-1190000000-355691f711b0faad45c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c8c452fd99c6bb4f3631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-1ce9bb01eb35f26908c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-f2f475ae4c62e877a9baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-9de0edc3a8b815dd7071Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abd-0940000000-d28d8b5f304b6ca1a699Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aos-2900000000-0737f10b02bfa62847f5Spectrum
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 IDDB01526
HMDB IDHMDB0005849
FooDB IDFDB023781
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link4-Androstenediol
Chemspider ID120071
ChEBI ID34386
PubChem Compound ID136297
Kegg Compound IDC14210
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Thuyne WV, Delbeke FT: Validation of a GC-MS screening method for anabolizing agents in aqueous nutritional supplements. J Chromatogr Sci. 2005 Jan;43(1):2-6.
2. Van Thuyne W, Delbeke FT: Validation of a GC-MS screening method for anabolizing agents in solid nutritional supplements. Biomed Chromatogr. 2004 Apr;18(3):155-9.
3. Earnest CP, Olson MA, Broeder CE, Breuel KF, Beckham SG: In vivo 4-androstene-3,17-dione and 4-androstene-3 beta,17 beta-diol supplementation in young men. Eur J Appl Physiol. 2000 Feb;81(3):229-32.
4. Parr MK, Geyer H, Reinhart U, Schanzer W: Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements. Food Addit Contam. 2004 Jul;21(7):632-40.