Bolasterone (CHEM036029)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:09:54 UTC
Update Date2016-11-09 01:21:25 UTC
Accession NumberCHEM036029
Identification
Common NameBolasterone
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass316.478 g/mol
Monoisotopic Mass316.240 g/mol
CAS Registry Number1605-89-6
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
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 IdentifierInChI=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
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 Solubility0.011 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-0292000000-d45cc06905f97c71acb7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-1219000000-a3d8e93a3429c1b5b79eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0095000000-24b926788859812bd140Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0291000000-d17e4bd109b597541b52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi9-3490000000-b1ee70c1893fd95ab783Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-6f88574915ba36904edeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0059000000-88ccda88856d7b515ee6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-0090000000-6f3e258701147d991147Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-be6e06313d0abca8e664Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-be6e06313d0abca8e664Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0097000000-3e67e2b99b64bbb19ddeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0749000000-4e378b170e7e0e501a17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-3911000000-3d55560ae9987134faebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-0900000000-1206f2feee3fa74b8674Spectrum
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 IDDB01471
HMDB IDHMDB0006048
FooDB IDFDB023820
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBolasterone
Chemspider ID92280
ChEBI ID529021
PubChem Compound ID102146
Kegg Compound IDC14475
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
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. Hatton CK, Catlin DH: Detection of androgenic anabolic steroids in urine. Clin Lab Med. 1987 Sep;7(3):655-68.
7. Brower KJ: Anabolic steroids. Psychiatr Clin North Am. 1993 Mar;16(1):97-103.
8. Schanzer W: Metabolism of anabolic androgenic steroids. Clin Chem. 1996 Jul;42(7):1001-20.
9. 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.