6beta-Hydroxytestosterone (CHEM022720)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:48:53 UTC
Update Date2016-11-09 01:17:34 UTC
Accession NumberCHEM022720
Identification
Common Name6beta-Hydroxytestosterone
ClassSmall Molecule
DescriptionTestosterone is reported to have an acute vasodilating action in vitro, an effect that may impart a favourable haemodynamic response in patients with chronic heart failure.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(6beta,17beta)-6,17-Dihydroxyandrost-4-en-3-oneChEBI
4-Androsten-6beta,17beta-diol-3-oneChEBI
6beta,17beta-Dihydroxy-4-androsten-3-oneChEBI
6beta,17beta-Dihydroxyandrost-4-en-3-oneChEBI
(6b,17b)-6,17-Dihydroxyandrost-4-en-3-oneGenerator
(6Β,17β)-6,17-dihydroxyandrost-4-en-3-oneGenerator
4-Androsten-6b,17b-diol-3-oneGenerator
4-Androsten-6β,17β-diol-3-oneGenerator
6b,17b-Dihydroxy-4-androsten-3-oneGenerator
6Β,17β-dihydroxy-4-androsten-3-oneGenerator
6b,17b-Dihydroxyandrost-4-en-3-oneGenerator
6Β,17β-dihydroxyandrost-4-en-3-oneGenerator
6b-HydroxytestosteroneGenerator
6Β-hydroxytestosteroneGenerator
6 beta-HydroxytestosteroneMeSH
6 beta-Hydroxytestosterone, (17beta)-isomerMeSH
6 beta-Hydroxytestosterone, (6alpha,17beta)-isomerMeSH
6 beta Hydroxy testosteroneHMDB
6,17-Dihydroxy-(6b,17b)-androst-4-en-3-oneHMDB
6,17-Dihydroxy-(6beta,17beta)-androst-4-en-3-oneHMDB
6,17-Dihydroxyandrost-4-en-3-one (acd/name 4.0)HMDB
Chemical FormulaC19H28O3
Average Molecular Mass304.424 g/mol
Monoisotopic Mass304.204 g/mol
CAS Registry Number62-99-7
IUPAC Name(1S,2R,8R,10R,11S,14S,15S)-8,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name6β-hydroxytestosterone
SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)C2=CC(=O)CC[C@]12C
InChI IdentifierInChI=1S/C19H28O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14,16-17,21-22H,3-8,10H2,1-2H3/t12-,13-,14-,16+,17-,18+,19-/m0/s1
InChI KeyXSEGWEUVSZRCBC-ZVBLRVHNSA-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
  • 17-hydroxysteroid
  • Oxosteroid
  • 6-hydroxysteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.095 g/LALOGPS
logP2.09ALOGPS
logP2.13ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)14.55ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.95 m³·mol⁻¹ChemAxon
Polarizability34.69 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, Positivesplash10-002r-0490000000-fbce40562e85113343e0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-3201900000-19a880626afdcb624da4Spectrum
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, Positivesplash10-00kr-0092000000-489bed8773fcd0c13de6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0090000000-f07fc698e115a5f1c7cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvl-3490000000-3c10f54e817114fb8e5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-2030860ac7b87d34beb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0097000000-0f7ab0e063794ee5cfd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-1190000000-d45875a741e3ea1e7526Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0019000000-9b79f62ea088c74b3a3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1794000000-57b269ff6c81d8c47be7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3910000000-eed8482fba4fd9079a6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-93986d59045cc7fce551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-93986d59045cc7fce551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbi-0092000000-1bd122937767d0574fc2Spectrum
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 IDHMDB0006259
FooDB IDFDB023864
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID18558308
ChEBI ID34477
PubChem Compound ID18603089
Kegg Compound IDC14497
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Furuta Takashi; Suzuki Atsushi; Matsuzawa Mitsuhiro; Shibasaki Hiromi; Kasuya Yasuji Syntheses of stable isotope-labeled 6 beta-hydroxycortisol, 6 beta-hydroxycortisone, and 6 beta-hydroxytestosterone. Steroids (2003), 68(7-8), 693-703.
2. Testino SA Jr, Ozarowski J, Thurston AW, Arrendale RF, Patonay G: Determination of testosterone and 6beta-hydroxytestosterone by gas chromatography-selected ion monitoring-mass spectrometry for the characterization of cytochrome p450 3A activity. J Chromatogr B Biomed Sci Appl. 1999 Oct 29;734(1):73-81.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10574192
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15203039
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22822673