16alpha-Hydroxyandrost-4-ene-3,17-dione (CHEM036237)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:20:08 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036237
Identification
Common Name16alpha-Hydroxyandrost-4-ene-3,17-dione
ClassSmall Molecule
Description16alpha-Hydroxyandrost-4-ene-3,17-dione is involved in androgen and estrogen metabolism. 16alpha-Hydroxyandrost-4-ene-3,17-dione is produced from dehydroepiandrosterone through the work of 2 enzymes, [E1.14.99.-] and 3beta-hydroxy-delta5-steroid dehydrogenase [EC:1.1.1.145].
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-Androsten-16alpha-ol-3,17-dioneChEBI
4-Androsten-16a-ol-3,17-dioneGenerator
4-Androsten-16α-ol-3,17-dioneGenerator
16 alpha-Hydroxyandrost-4-en-3,17-dioneMeSH
16-Hydroxyandrost-4-en-3,17-dioneMeSH
16-Hydroxyandrost-4-en-3,17-dione, (16alpha)-isomerMeSH
16-Hydroxyandrost-4-en-3,17-dione, (16beta)-isomerMeSH
16alpha-OHADMeSH
16alpha-Hydroxyandrost-4-ene-3,17-dioneHMDB
16alpha-HydroxyandrostenedioneMeSH, HMDB
16a-Hydroxyandrost-4-ene-3,17-dioneGenerator
16Α-hydroxyandrost-4-ene-3,17-dioneGenerator
Chemical FormulaC19H26O3
Average Molecular Mass302.408 g/mol
Monoisotopic Mass302.188 g/mol
CAS Registry Number63-02-5
IUPAC Name(1S,2R,10R,11S,13R,15S)-13-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione
Traditional Name4-androsten-16α-ol-3,17-dione
SMILES[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/C19H26O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h9,13-16,21H,3-8,10H2,1-2H3/t13-,14+,15+,16-,18+,19+/m1/s1
InChI KeySSBCZTXGVMMZOT-NBBHSKLNSA-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-oxo-delta-4-steroid
  • 3-oxosteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • 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 Solubility0.067 g/LALOGPS
logP2.32ALOGPS
logP3.06ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)13.38ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.1 m³·mol⁻¹ChemAxon
Polarizability33.99 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, Positivesplash10-006x-0190000000-333d436ce8b783dec900Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ldj-1029000000-d779bb8112f47f4675a3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0169000000-552881f7e148e949c2d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fi9-0191000000-5bba772cd2498247059bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ldl-3390000000-dcf95e7ad7d31a7b2345Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-0e8dc36bc54906d11cd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0029000000-e08d062d1b3fb4e55267Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bo-1090000000-86e6dcdcc4e4babac09eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0049000000-79630e98940a556508ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-114s-0972000000-fef31191241a5fee6d7aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r7-1910000000-e9b6c3405a956f782301Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-4360bacaf95498925fe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0039000000-479f11c50b787985f7d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0091000000-9edb0c3dd24f9aa0965bSpectrum
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 IDHMDB0006774
FooDB IDFDB024076
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID389474
ChEBI ID27582
PubChem Compound ID440574
Kegg Compound IDC05140
YMDB IDNot Available
ECMDB IDM2MDB005825
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available