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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-04-12 21:14:39 UTC
Update Date2022-03-07 02:49:29 UTC
HMDB IDHMDB0006048
Secondary Accession Numbers
  • HMDB06048
Metabolite Identification
Common NameBolasterone
DescriptionBolasterone is an anabolic androgenic steroid. Analysis of steroids in urine has been used to detect different hormonal actions in human beings such as testicular function in men, hyperandrogenic disorders in women and puberty problems in children, by the measurement of anabolic steroids, and some hormonal disorders such as adrenocortical adenoma and Cushing syndrome by the control of corticoids. This steroid have been included in the International Olympic Committee (IOC) doping list due to their illegal use in some sports and in the list of schedules drugs in several countries because of its use by young people. In addition, the examination of endogenous steroids profile provides information about the health and the use of exogenous steroids. Bolasterone is excreted as the original compound in human urine. Androgenic anabolic steroids (AAS) 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: 10892583 , 10932808 , 14976846 , 15042372 , 15231229 , 3308301 , 8456050 , 8674183 , 16040239 ).
Structure
Data?1582752373
Synonyms
ValueSource
7alpha,17alpha-DimethyltestosteroneKegg
17beta-Hydroxy-7alpha,17-dimethylandrost-4-en-3-oneKegg
U19763Kegg
7a,17a-DimethyltestosteroneGenerator
7Α,17α-dimethyltestosteroneGenerator
17b-Hydroxy-7a,17-dimethylandrost-4-en-3-oneGenerator
17Β-hydroxy-7α,17-dimethylandrost-4-en-3-oneGenerator
(7a,17b)-17-Hydroxy-7,17-dimethyl-androst-4-en-3-oneHMDB
17b-Hydroxy-7a,17-dimethyl-androst-4-en-3-oneHMDB
17b-Hydroxy-7a,17a-dimethylandrost-4-ene-3-oneHMDB
7a,17-Dimethyl-testosteroneHMDB
7a,17a-Dimethyl-17b-hydroxyandrost-4-en-3-oneHMDB
MyagenHMDB
Chemical FormulaC21H32O2
Average Molecular Weight316.4776
Monoisotopic Molecular Weight316.240230268
IUPAC Name(1S,2R,9R,10R,11S,14S,15S)-14-hydroxy-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Namebolasterone
CAS Registry Number1605-89-6
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)CC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O2/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/h12-13,16-18,23H,5-11H2,1-4H3/t13-,16+,17+,18-,19+,20+,21+/m1/s1
InChI KeyIVFYLRMMHVYGJH-VLOLGRDOSA-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
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Tertiary alcohol
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point164 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.55ALOGPS
logP3.93ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)19.56ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity93.62 m³·mol⁻¹ChemAxon
Polarizability37.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.1631661259
DarkChem[M-H]-172.52631661259
DeepCCS[M-2H]-211.91230932474
DeepCCS[M+Na]+186.42430932474
AllCCS[M+H]+180.232859911
AllCCS[M+H-H2O]+177.332859911
AllCCS[M+NH4]+182.932859911
AllCCS[M+Na]+183.732859911
AllCCS[M-H]-187.232859911
AllCCS[M+Na-2H]-187.632859911
AllCCS[M+HCOO]-188.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Bolasterone[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)CC2=CC(=O)CC[C@]12C3592.7Standard polar33892256
Bolasterone[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)CC2=CC(=O)CC[C@]12C2653.3Standard non polar33892256
Bolasterone[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@H](C)CC2=CC(=O)CC[C@]12C2808.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Bolasterone,1TMS,isomer #1C[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O[Si](C)(C)C)[C@@H]212816.3Semi standard non polar33892256
Bolasterone,1TMS,isomer #2C[C@@H]1CC2=CC(O[Si](C)(C)C)=CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@]3(C)O)[C@@H]212688.8Semi standard non polar33892256
Bolasterone,2TMS,isomer #1C[C@@H]1CC2=CC(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]212747.6Semi standard non polar33892256
Bolasterone,2TMS,isomer #1C[C@@H]1CC2=CC(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]212787.3Standard non polar33892256
Bolasterone,2TMS,isomer #1C[C@@H]1CC2=CC(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]212854.2Standard polar33892256
Bolasterone,1TBDMS,isomer #1C[C@@H]1CC2=CC(=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]213052.8Semi standard non polar33892256
Bolasterone,1TBDMS,isomer #2C[C@@H]1CC2=CC(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]212958.6Semi standard non polar33892256
Bolasterone,2TBDMS,isomer #1C[C@@H]1CC2=CC(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]213263.7Semi standard non polar33892256
Bolasterone,2TBDMS,isomer #1C[C@@H]1CC2=CC(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]213250.2Standard non polar33892256
Bolasterone,2TBDMS,isomer #1C[C@@H]1CC2=CC(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]213074.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Bolasterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-0292000000-d45cc06905f97c71acb72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bolasterone GC-MS (1 TMS) - 70eV, Positivesplash10-00di-1219000000-a3d8e93a3429c1b5b79e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bolasterone 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 - Bolasterone 10V, Negative-QTOFsplash10-014i-0029000000-6f88574915ba36904ede2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bolasterone 20V, Negative-QTOFsplash10-014i-0059000000-88ccda88856d7b515ee62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bolasterone 40V, Negative-QTOFsplash10-00kb-0090000000-6f3e258701147d9911472017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bolasterone 10V, Negative-QTOFsplash10-014i-0009000000-be6e06313d0abca8e6642021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bolasterone 20V, Negative-QTOFsplash10-014i-0009000000-be6e06313d0abca8e6642021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bolasterone 40V, Negative-QTOFsplash10-014i-0097000000-3e67e2b99b64bbb19dde2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bolasterone 10V, Positive-QTOFsplash10-00kb-0095000000-24b926788859812bd1402017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bolasterone 20V, Positive-QTOFsplash10-00kb-0291000000-d17e4bd109b597541b522017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bolasterone 40V, Positive-QTOFsplash10-0zi9-3490000000-b1ee70c1893fd95ab7832017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bolasterone 10V, Positive-QTOFsplash10-014i-0749000000-4e378b170e7e0e501a172021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bolasterone 20V, Positive-QTOFsplash10-002f-3911000000-3d55560ae9987134faeb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bolasterone 40V, Positive-QTOFsplash10-000f-0900000000-1206f2feee3fa74b86742021-09-24Wishart 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 IDDB01471
Phenol Explorer Compound IDNot Available
FooDB IDFDB023820
KNApSAcK IDNot Available
Chemspider ID92280
KEGG Compound IDC14475
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBolasterone
METLIN IDNot Available
PubChem Compound102146
PDB IDNot Available
ChEBI ID529021
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. 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. [PubMed:16040239 ]
  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. Hatton CK, Catlin DH: Detection of androgenic anabolic steroids in urine. Clin Lab Med. 1987 Sep;7(3):655-68. [PubMed:3308301 ]
  7. Brower KJ: Anabolic steroids. Psychiatr Clin North Am. 1993 Mar;16(1):97-103. [PubMed:8456050 ]
  8. Schanzer W: Metabolism of anabolic androgenic steroids. Clin Chem. 1996 Jul;42(7):1001-20. [PubMed:8674183 ]
  9. Gonzalo-Lumbreras R, Izquierdo-Hornillos R: Optimization of the high-performance liquid chromatographic separation of a complex mixture containing urinary steroids, boldenone and bolasterone: application to urine samples. J Chromatogr B Biomed Sci Appl. 2000 May 26;742(1):47-57. [PubMed:10892583 ]