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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-04-12 20:20:42 UTC
Update Date2021-09-14 15:40:23 UTC
HMDB IDHMDB0006013
Secondary Accession Numbers
  • HMDB06013
Metabolite Identification
Common Name7a,17-dimethyl-5b-Androstane-3a,17b-diol
Description7a,17-dimethyl-5b-Androstane-3a,17b-diol is a urinary metabolite of the anabolic androgenic steroid (AAS) bolasterone. Androgenic anabolic steroids are defined as natural, synthetic or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic and neuro-endocrine systems, the AAS have been extensively used in sports activities. The use of anabolic steroids was banned by the International Olympic Committee for the first time at the Olympic Games in Montreal in 1976. Since that time the misuse of anabolic steroids by athletes has been controlled by analysis of urine of the excreted steroids or their metabolites, or both. (PMID: 10932808 , 14976846 , 15042372 , 15231229 , 16195040 , 16292586 , 1663826 , 16799097 , 16888758 , 16923823 , 17667636 , 17723876 , 17723877 , 2079979 , 3308301 , 8456050 , 8674183 , 8725393 , 9216475 ).
Structure
Data?1582752371
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 Weight320.5093
Monoisotopic Molecular Weight320.271530396
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
CAS Registry Number13611-10-4
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 Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.24631661259
DarkChem[M-H]-170.25231661259
DeepCCS[M-2H]-214.36930932474
DeepCCS[M+Na]+188.58130932474
AllCCS[M+H]+183.032859911
AllCCS[M+H-H2O]+180.332859911
AllCCS[M+NH4]+185.532859911
AllCCS[M+Na]+186.232859911
AllCCS[M-H]-186.832859911
AllCCS[M+Na-2H]-187.432859911
AllCCS[M+HCOO]-188.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7a,17-dimethyl-5b-Androstane-3a,17b-diol[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@]12C2648.9Standard polar33892256
7a,17-dimethyl-5b-Androstane-3a,17b-diol[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@]12C2590.0Standard non polar33892256
7a,17-dimethyl-5b-Androstane-3a,17b-diol[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@]12C2649.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7a,17-dimethyl-5b-Androstane-3a,17b-diol,1TMS,isomer #1C[C@@H]1C[C@@H]2C[C@H](O)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C)[C@@H]212645.1Semi standard non polar33892256
7a,17-dimethyl-5b-Androstane-3a,17b-diol,1TMS,isomer #2C[C@@H]1C[C@@H]2C[C@H](O[Si](C)(C)C)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O)[C@@H]212616.7Semi standard non polar33892256
7a,17-dimethyl-5b-Androstane-3a,17b-diol,2TMS,isomer #1C[C@@H]1C[C@@H]2C[C@H](O[Si](C)(C)C)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C)[C@@H]212653.9Semi standard non polar33892256
7a,17-dimethyl-5b-Androstane-3a,17b-diol,1TBDMS,isomer #1C[C@@H]1C[C@@H]2C[C@H](O)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C(C)(C)C)[C@@H]212912.6Semi standard non polar33892256
7a,17-dimethyl-5b-Androstane-3a,17b-diol,1TBDMS,isomer #2C[C@@H]1C[C@@H]2C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O)[C@@H]212886.3Semi standard non polar33892256
7a,17-dimethyl-5b-Androstane-3a,17b-diol,2TBDMS,isomer #1C[C@@H]1C[C@@H]2C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C(C)(C)C)[C@@H]213198.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-06tf-0192000000-febaf71cb7bb3ce7ddab2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol GC-MS (2 TMS) - 70eV, Positivesplash10-0002-2126900000-792439d40f989622f2842017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 10V, Positive-QTOFsplash10-0uk9-0029000000-19a3ae7b670c2bbc4f912017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 20V, Positive-QTOFsplash10-0udr-0395000000-d86de9a9b8e51a4e333e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 40V, Positive-QTOFsplash10-000f-2690000000-2828700e527e4071dd842017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 10V, Negative-QTOFsplash10-014i-0009000000-d7324ee3eff729ce20da2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 20V, Negative-QTOFsplash10-0gb9-0009000000-59443a42cdd02a1faa332017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 40V, Negative-QTOFsplash10-0ug0-1093000000-fc68bc0074752ab0a64d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 10V, Positive-QTOFsplash10-0uk9-0129000000-ba68bf173da2e0146d032021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 20V, Positive-QTOFsplash10-0002-6923000000-bc7dd3eeba9b6e3b61632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 40V, Positive-QTOFsplash10-0007-3900000000-7addaf6a3692944c13372021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 10V, Negative-QTOFsplash10-014i-0009000000-a90d3a3bae4a1d75273f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 20V, Negative-QTOFsplash10-014i-0009000000-a90d3a3bae4a1d75273f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7a,17-dimethyl-5b-Androstane-3a,17b-diol 40V, Negative-QTOFsplash10-014i-0019000000-8c6fb945dd6e4541f7e42021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023802
KNApSAcK IDNot Available
Chemspider ID23254171
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15706076
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:16799097 ]
  2. Yesalis CE, Bahrke MS: Doping among adolescent athletes. Baillieres Best Pract Res Clin Endocrinol Metab. 2000 Mar;14(1):25-35. [PubMed:10932808 ]
  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. [PubMed:14976846 ]
  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. [PubMed:15042372 ]
  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. [PubMed:15231229 ]
  6. Maughan RJ: Contamination of dietary supplements and positive drug tests in sport. J Sports Sci. 2005 Sep;23(9):883-9. [PubMed:16195040 ]
  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. [PubMed:16292586 ]
  8. VanHelder WP, Kofman E, Tremblay MS: Anabolic steroids in sport. Can J Sport Sci. 1991 Dec;16(4):248-57. [PubMed:1663826 ]
  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. [PubMed:16888758 ]
  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. [PubMed:16923823 ]
  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. [PubMed:17667636 ]
  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. [PubMed:17723876 ]
  13. Smurawa TM, Congeni JA: Testosterone precursors: use and abuse in pediatric athletes. Pediatr Clin North Am. 2007 Aug;54(4):787-96, xii. [PubMed:17723877 ]
  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. [PubMed:2079979 ]
  15. Hatton CK, Catlin DH: Detection of androgenic anabolic steroids in urine. Clin Lab Med. 1987 Sep;7(3):655-68. [PubMed:3308301 ]
  16. Brower KJ: Anabolic steroids. Psychiatr Clin North Am. 1993 Mar;16(1):97-103. [PubMed:8456050 ]
  17. Schanzer W: Metabolism of anabolic androgenic steroids. Clin Chem. 1996 Jul;42(7):1001-20. [PubMed:8674183 ]
  18. Lukas SE: CNS effects and abuse liability of anabolic-androgenic steroids. Annu Rev Pharmacol Toxicol. 1996;36:333-57. [PubMed:8725393 ]
  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. [PubMed:9216475 ]