4b-Hydroxystanozolol (CHEM035507)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:49:49 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035507
Identification
Common Name4b-Hydroxystanozolol
ClassSmall Molecule
Description4b-Hydroxystanozolol is a metabolite of stanozolol. Stanozolol has the potential for misuse as an anabolic steroid in horse racing. Stanozolol is an anabolic steroid illicitly used for growth promoting purposes in animal production. For reasons of public health the use of anabolic steroids as growth promoters is officially banned in Europe in animals intended for consumption. Stanozolol is a synthetic anabolic androgenic steroid often abused in sports to enhance performance. Doping control screening for the analysis of anabolic steroids in human urine or the detection of anabolic steroid residues in cattle's urine is achieved using liquid and gas chromatography time-of-flight mass spectrometry, liquid chromatography-tandem mass spectrometry or through a combination of liquid chromatography/tandem mass spectrometry and gas chromatography/mass spectrometry. (PMID: 16040239, 17724580, 17610244, 15782394).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(4b,5a,17b)-17-Methyl-2'H-androst-2-eno[3,2-c]pyrazole-4,17-diolHMDB
4b-OH-StanozololHMDB
4beta-HydroxystanozololHMDB
Cyclopenta[7,8]phenanthro[2,3-c]pyrazole 2'H-androst-2-eno[3,2-c]pyrazole-4,17-diol deriv.HMDB
Chemical FormulaC21H32N2O2
Average Molecular Mass344.491 g/mol
Monoisotopic Mass344.246 g/mol
CAS Registry Number125636-92-2
IUPAC Name(1S,2R,9R,10R,13R,14S,17S,18S)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4(8),5-diene-9,17-diol
Traditional Name(1S,2R,9R,10R,13R,14S,17S,18S)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4(8),5-diene-9,17-diol
SMILES[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])[C@@H](O)C3=C(C[C@]12C)C=NN3
InChI IdentifierInChI=1S/C21H32N2O2/c1-19-10-12-11-22-23-17(12)18(24)16(19)5-4-13-14(19)6-8-20(2)15(13)7-9-21(20,3)25/h11,13-16,18,24-25H,4-10H2,1-3H3,(H,22,23)/t13-,14+,15+,16+,18-,19-,20+,21+/m1/s1
InChI KeyOCUSYXNRARMJHS-SUVJOWDWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • Estrane-skeleton
  • 4-hydroxysteroid
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Azole
  • Cyclic alcohol
  • Pyrazole
  • Tertiary alcohol
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.02 g/LALOGPS
logP2.93ALOGPS
logP2.7ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)13.75ChemAxon
pKa (Strongest Basic)1.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity98.54 m³·mol⁻¹ChemAxon
Polarizability40.06 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-00or-0359000000-0f134279c73ede2dfb19Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-2013900000-570ee78d58d7e1f57eebSpectrum
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, Positivesplash10-004i-0009000000-072017f9a5446fbf31a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-2079000000-cc0727df2fc91ce42e51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-9513000000-d38b2a43ed8ef01cf863Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-c5c4fa8fa856784dd5f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ov-0019000000-b88ee2c0dfea5cb32728Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2049000000-33814ebb11889f38fe27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-f0c9f6f6d6de10398e83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-b6d1574e79022e9c9f59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-0019000000-24be4b8b2ce190c4242aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0019000000-a9ee0abfecf2da386d7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2794000000-ea9b314b90ba7e8c6771Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-1290000000-2f1310462383fa6e8904Spectrum
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 IDHMDB0003318
FooDB IDFDB023137
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776560
ChEBI IDNot Available
PubChem Compound ID53477768
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Hungerford NL, Sortais B, Smart CG, McKinney AR, Ridley DD, Stenhouse AM, Suann CJ, Munn KJ, Sillence MN, McLeod MD: Analysis of anabolic steroids in the horse: development of a generic ELISA for the screening of 17alpha-alkyl anabolic steroid metabolites. J Steroid Biochem Mol Biol. 2005 Aug;96(3-4):317-34.
2. Mateus-Avois L, Mangin P, Saugy M: Use of ion trap gas chromatography-multiple mass spectrometry for the detection and confirmation of 3'hydroxystanozolol at trace levels in urine for doping control. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Feb 25;816(1-2):193-201.
3. 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.
4. 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.
5. Van Poucke C, Van De Velde M, Van Peteghem C: Combination of liquid chromatography/tandem mass spectrometry and gas chromatography/mass spectrometry for the detection of 21 anabolic steroid residues in bovine urine. J Mass Spectrom. 2005 Jun;40(6):731-8.