6b-Hydroxymethandienone (CHEM036002)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:08:56 UTC
Update Date2016-11-09 01:21:25 UTC
Accession NumberCHEM036002
Identification
Common Name6b-Hydroxymethandienone
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6b,17b)-6,17-Dihydroxy-17-methyl-androsta-1,4-dien-3-oneHMDB
6b,17b-Dihydroxy-17-methyl-androsta-1,4-dien-3-oneHMDB
6b-HydroxydianabolHMDB
6b-HydroxymethandrostenoloneHMDB
Chemical FormulaC20H28O3
Average Molecular Mass316.435 g/mol
Monoisotopic Mass316.204 g/mol
CAS Registry Number33526-41-9
IUPAC Name(1S,2R,8R,10R,11S,14S,15S)-8,14-dihydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
Traditional Name6b-hydroxydianabol
SMILES[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C[C@@H](O)C2=CC(=O)C=C[C@]12C
InChI IdentifierInChI=1S/C20H28O3/c1-18-7-4-12(21)10-16(18)17(22)11-13-14(18)5-8-19(2)15(13)6-9-20(19,3)23/h4,7,10,13-15,17,22-23H,5-6,8-9,11H2,1-3H3/t13-,14+,15+,17-,18-,19+,20+/m1/s1
InChI KeyOBCJFTMGLMNCTJ-INIPNLRTSA-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-1,4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • 6-hydroxysteroid
  • Hydroxysteroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Tertiary 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 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 Solubility0.13 g/LALOGPS
logP2.62ALOGPS
logP2.41ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)14.53ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity91.68 m³·mol⁻¹ChemAxon
Polarizability35.85 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, Positivesplash10-0ukj-0592000000-5c587db71915b7f745d9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-002b-4234900000-61a5337db6621fc5bef5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0092000000-5895e4b865d6d32e6c22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0190000000-61be85dce027bd95d308Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05v0-3290000000-d6f6e99de49064f16ddcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0049000000-8591676ba45f009be5e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0098000000-45a0e7b9cb41bc3e25b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0190000000-bc5b69c787b6a3cf983cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-d337ec43015bf5d00be6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0019000000-4b20c3056a9293051876Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0671-0391000000-b690824c05d4dc1ecdc5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0097000000-cfa23bedd70d14ce08c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n4-1972000000-6f8b2da223795e39466aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-3970000000-3e72eb66848076ae35f6Spectrum
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 IDHMDB0005832
FooDB IDFDB023778
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10363911
ChEBI IDNot Available
PubChem Compound ID13241205
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Pryakhina, Z. A.; Grinenko, G. S.; Lisitsa, L. I.; Gritsina, G. I. On the dehydrogenation of methytestosterone by selenious acid. Khimiko-Farmatsevticheskii Zhurnal (1976), 10(1), 115-17.
2. 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.
3. Durbeck HW, Buker I, Scheulen B, Telin B: Gas chromatographic and capillary column gas chromatographic--mass spectrometric determination of synthetic anabolic steroids. I. Methandienone and its metabolites. J Chromatogr. 1978 Dec 21;167:117-24.
4. Bowers LD, Borts DJ: Separation and confirmation of anabolic steroids with quadrupole ion trap tandem mass spectrometry. J Chromatogr B Biomed Appl. 1996 Dec 6;687(1):69-78.
5. Harrison LM, Martin D, Gotlin RW, Fennessey PV: Effect of extended use of single anabolic steroids on urinary steroid excretion and metabolism. J Chromatogr. 1989 Apr 7;489(1):121-6.
6. Marcos J, Pascual JA, de la Torre X, Segura J: Fast screening of anabolic steroids and other banned doping substances in human urine by gas chromatography/tandem mass spectrometry. J Mass Spectrom. 2002 Oct;37(10):1059-73.
7. Schanzer W, Horning S, Donike M: Metabolism of anabolic steroids in humans: synthesis of 6 beta-hydroxy metabolites of 4-chloro-1,2-dehydro-17 alpha-methyltestosterone, fluoxymesterone, and metandienone. Steroids. 1995 Apr;60(4):353-66.
8. Hagedorn HW, Schulz R, Friedrich A: Detection of methandienone (methandrostenolone) and metabolites in horse urine by gas chromatography-mass spectrometry. J Chromatogr. 1992 Jun 10;577(2):195-203.
9. 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.