7a,17-Dimethyl-5b-androstane-3a,17b-diol (CHEM036017)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:09:35 UTC
Update Date2016-11-09 01:21:25 UTC
Accession NumberCHEM036017
Identification
Common Name7a,17-Dimethyl-5b-androstane-3a,17b-diol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3a,5b,7a,17b)-7,17-Dimethyl-androstane-3,17-diolHMDB
7a,17a-Dimethyl-5b-androstane-3a,17b-diolHMDB
Chemical FormulaC21H36O2
Average Molecular Mass320.509 g/mol
Monoisotopic Mass320.272 g/mol
CAS Registry Number13611-10-4
IUPAC Name(1S,2S,5R,7R,9R,10R,11S,14S,15S)-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
Traditional Name(1S,2S,5R,7R,9R,10R,11S,14S,15S)-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
SMILES[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)C[C@]2([H])C[C@H](O)CC[C@]12C
InChI IdentifierInChI=1S/C21H36O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h13-18,22-23H,5-12H2,1-4H3/t13-,14-,15-,16+,17+,18-,19+,20+,21+/m1/s1
InChI KeyZWQUPIDNCOVROC-HEEAJRSSSA-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
  • 17-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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 Solubility0.0022 g/LALOGPS
logP4.23ALOGPS
logP3.77ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity93.82 m³·mol⁻¹ChemAxon
Polarizability38.64 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, Positivesplash10-06tf-0192000000-febaf71cb7bb3ce7ddabSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-2126900000-792439d40f989622f284Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0029000000-19a3ae7b670c2bbc4f91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-0395000000-d86de9a9b8e51a4e333eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-2690000000-2828700e527e4071dd84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-d7324ee3eff729ce20daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0009000000-59443a42cdd02a1faa33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ug0-1093000000-fc68bc0074752ab0a64dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0129000000-ba68bf173da2e0146d03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-6923000000-bc7dd3eeba9b6e3b6163Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-3900000000-7addaf6a3692944c1337Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-a90d3a3bae4a1d75273fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-a90d3a3bae4a1d75273fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0019000000-8c6fb945dd6e4541f7e4Spectrum
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 IDHMDB0006013
FooDB IDFDB023802
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID23254171
ChEBI IDNot Available
PubChem Compound ID15706076
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Saudan C, Baume N, Robinson N, Avois L, Mangin P, Saugy M: Testosterone and doping control. Br J Sports Med. 2006 Jul;40 Suppl 1:i21-4.
2. Yesalis CE, Bahrke MS: Doping among adolescent athletes. Baillieres Best Pract Res Clin Endocrinol Metab. 2000 Mar;14(1):25-35.
3. Furlanello F, Bentivegna S, Cappato R, De Ambroggi L: Arrhythmogenic effects of illicit drugs in athletes. Ital Heart J. 2003 Dec;4(12):829-37.
4. Bricout V, Wright F: Update on nandrolone and norsteroids: how endogenous or xenobiotic are these substances? Eur J Appl Physiol. 2004 Jun;92(1-2):1-12. Epub 2004 Mar 20.
5. Foster ZJ, Housner JA: Anabolic-androgenic steroids and testosterone precursors: ergogenic aids and sport. Curr Sports Med Rep. 2004 Aug;3(4):234-41.
6. Maughan RJ: Contamination of dietary supplements and positive drug tests in sport. J Sports Sci. 2005 Sep;23(9):883-9.
7. Fineschi V, Riezzo I, Centini F, Silingardi E, Licata M, Beduschi G, Karch SB: Sudden cardiac death during anabolic steroid abuse: morphologic and toxicologic findings in two fatal cases of bodybuilders. Int J Legal Med. 2007 Jan;121(1):48-53. Epub 2005 Nov 15.
8. VanHelder WP, Kofman E, Tremblay MS: Anabolic steroids in sport. Can J Sport Sci. 1991 Dec;16(4):248-57.
9. Thevis M, Schanzer W: Mass spectrometry in sports drug testing: Structure characterization and analytical assays. Mass Spectrom Rev. 2007 Jan-Feb;26(1):79-107.
10. Green GA: Doping control for the team physician: a review of drug testing procedures in sport. Am J Sports Med. 2006 Oct;34(10):1690-8. Epub 2006 Aug 21.
11. Furlanello F, Serdoz LV, Cappato R, De Ambroggi L: Illicit drugs and cardiac arrhythmias in athletes. Eur J Cardiovasc Prev Rehabil. 2007 Aug;14(4):487-94.
12. Kerr JM, Congeni JA: Anabolic-androgenic steroids: use and abuse in pediatric patients. Pediatr Clin North Am. 2007 Aug;54(4):771-85, xii.
13. Smurawa TM, Congeni JA: Testosterone precursors: use and abuse in pediatric athletes. Pediatr Clin North Am. 2007 Aug;54(4):787-96, xii.
14. Yesalis CE, Anderson WA, Buckley WE, Wright JE: Incidence of the nonmedical use of anabolic-androgenic steroids. NIDA Res Monogr. 1990;102:97-112.
15. Hatton CK, Catlin DH: Detection of androgenic anabolic steroids in urine. Clin Lab Med. 1987 Sep;7(3):655-68.
16. Brower KJ: Anabolic steroids. Psychiatr Clin North Am. 1993 Mar;16(1):97-103.
17. Schanzer W: Metabolism of anabolic androgenic steroids. Clin Chem. 1996 Jul;42(7):1001-20.
18. Lukas SE: CNS effects and abuse liability of anabolic-androgenic steroids. Annu Rev Pharmacol Toxicol. 1996;36:333-57.
19. Catlin DH, Hatton CK, Starcevic SH: Issues in detecting abuse of xenobiotic anabolic steroids and testosterone by analysis of athletes' urine. Clin Chem. 1997 Jul;43(7):1280-8.