Showing metabocard for 7a-Hydroxytestosterone (LMDB00442)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-07-13 19:49:57 UTC
Update Date2016-07-19 23:06:48 UTC
LmdbLMDB00442
Secondary Accession NumbersNone
Metabolite Identification
Common Name7a-Hydroxytestosterone
Description4-Hydroxytestosterone is the 17-hydroxylated analog to formestane. It is commercially available on the internet as anabolic steroid for oral self-administration and does not have any therapeutic indication. Hence, only little information is available about its metabolism. So far, most studies dealt with 4-hydroxytestosterone as metabolite of formestane while one study investigated the glucuronic acid conjugates of metabolic products of 4-hydroxytestosterone. This substance is prohibited in sports by the World Anti-Doping Agency; there is to a considerable increase of structurally related steroids with anabolic effects offered via the internet. 4-Hydroxytestosterone is a metabolite of the steroidal aromatase inhibitor 4-hydroxyandrost-4-ene-3,17-dione (4OHA). (PMID: 17724580 , 17610244 , 17207827 , 1284430 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(17beta)-4,17-Dihydroxy-androst-4-en-3-oneHMDB
(3b,17a)-Androst-5-ene-3,17-diolHMDB
3b,17a-Dihydroxyandrost-5-eneHMDB
4,17beta-Dihydroxy-4-androstene-3-oneHMDB
4-Androstene-7alpha-17beta-diol-3-oneHMDB
4-OHTHMDB
7alpha-HydroxytestosteroneHMDB
Androst-5-ene-3b,17a-diolHMDB
D5-Androstene-3b,17a-diolHMDB
4,17 beta-Dihydroxy-4-androstene-3-oneMeSH, HMDB
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(2R,14S,15S)-6,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Name(2R,14S,15S)-6,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
CAS Registry Number2141-17-5
SMILES
C[C@]12CCC3C(CCC4=C(O)C(=O)CC[C@]34C)C1CC[C@@H]2O
InChI Identifier
InChI=1S/C19H28O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,16,21-22H,3-10H2,1-2H3/t11?,12?,13?,16-,18+,19-/m0/s1
InChI KeyBQOIJSIMMIDHMO-XRJYYLNASA-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
  • 4-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Enol
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.48ALOGPS
logP2.85ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.4 m³·mol⁻¹ChemAxon
Polarizability34.89 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-0090000000-f8c70e9c073ebf34b059Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1022900000-600be045d8943f743d57Spectrum
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, Positivesplash10-052r-0095000000-1ed1d6e3a92671fd2ad0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-0391000000-688b70f5d7af33f8cee6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0041-6690000000-280160a24bfda119b38cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-e348bdb79d40a4c67d8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0069000000-414113628118ffc4436dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-1090000000-78462554e3a1a05a840cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-93986d59045cc7fce551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0019000000-92df155d883a35606e36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0095000000-c78824a01c7b942a579aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0049000000-dee580cc76c7cfcdaec8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-0590000000-4682faf86ab20fed64d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-4910000000-82ee78b7109f9f4b5333Spectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
SerumDetected and Quantified0.000949 uMNot AvailableBovine details
SerumDetected and Quantified0.0011 uMNot AvailableBovine details
SerumDetected and Quantified0.00116 uMNot AvailableBovine details
SerumDetected and Quantified0.000637&0.00108 uMNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0003956
FooDB IDFDB023273
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID53477776
Kegg Compound IDC05291
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pozo OJ, Van Eenoo P, Deventer K, Delbeke FT: Development and validation of a qualitative screening method for the detection of exogenous anabolic steroids in urine by liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem. 2007 Oct;389(4):1209-24. Epub 2007 Aug 28. [17724580 ]
  2. Georgakopoulos CG, Vonaparti A, Stamou M, Kiousi P, Lyris E, Angelis YS, Tsoupras G, Wuest B, Nielen MW, Panderi I, Koupparis M: Preventive doping control analysis: liquid and gas chromatography time-of-flight mass spectrometry for detection of designer steroids. Rapid Commun Mass Spectrom. 2007;21(15):2439-46. [17610244 ]
  3. Kohler M, Parr MK, Opfermann G, Thevis M, Schlorer N, Marner FJ, Schanzer W: Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: Mass spectrometric identification of urinary metabolites. Steroids. 2007 Mar;72(3):278-86. Epub 2007 Jan 17. [17207827 ]
  4. Davies JH, Shearer RJ, Rowlands MG, Poon GK, Houghton J, Jarman M, Dowsett M: Effects of 4-hydroxyandrost-4-ene-3,17-dione and its metabolites on 5 alpha-reductase activity and the androgen receptor. J Enzyme Inhib. 1992;6(2):141-7. [1284430 ]