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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-22 20:04:38 UTC
Update Date2017-10-23 19:04:20 UTC
HMDB IDHMDB0006259
Secondary Accession Numbers
  • HMDB06259
Metabolite Identification
Common Name6beta-Hydroxytestosterone
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.
Structure
Thumb
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
6b-HydroxytestosteroneGenerator
6β-hydroxytestosteroneGenerator
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
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
6 beta-Hydroxytestosterone, (17beta)-isomerMeSH
6 beta-HydroxytestosteroneMeSH
6 beta-Hydroxytestosterone, (6alpha,17beta)-isomerMeSH
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
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
CAS Registry Number62-99-7
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 Identifier
InChI=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
DescriptionThis compound 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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Tissue and substructures:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

  Molecular messenger:

Industrial application:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    System process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point172 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002r-0490000000-fbce40562e85113343e0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-3201900000-19a880626afdcb624da4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0092000000-489bed8773fcd0c13de6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0090000000-f07fc698e115a5f1c7cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvl-3490000000-3c10f54e817114fb8e5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-2030860ac7b87d34beb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-0097000000-0f7ab0e063794ee5cfd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dr-1190000000-d45875a741e3ea1e7526View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00392
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDFDB023864
      KNApSAcK IDNot Available
      Chemspider ID58987
      KEGG Compound IDC14497
      BioCyc IDNot Available
      BiGG ID2299953
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound65543
      PDB IDNot Available
      ChEBI ID34477
      References
      Synthesis ReferenceFuruta 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.
      Material Safety Data Sheet (MSDS)Download (PDF)
      General References
      1. 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. [PubMed:10574192 ]