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Showing Compound Bolasterone (FDB023820)

Record Information
Version1.0
Creation date2011-09-21 00:35:19 UTC
Update date2015-07-21 06:57:53 UTC
Primary IDFDB023820
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number1605-89-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H32O2
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
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
Isomeric 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
Average Molecular Weight316.4776
Monoisotopic Molecular Weight316.240230268
Classification
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
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBolasterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-0292000000-d45cc06905f97c71acb7Spectrum
Predicted GC-MSBolasterone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-1219000000-a3d8e93a3429c1b5b79eSpectrum
Predicted GC-MSBolasterone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0095000000-24b926788859812bd1402017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-0291000000-d17e4bd109b597541b522017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi9-3490000000-b1ee70c1893fd95ab7832017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-6f88574915ba36904ede2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0059000000-88ccda88856d7b515ee62017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-0090000000-6f3e258701147d9911472017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-be6e06313d0abca8e6642021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-be6e06313d0abca8e6642021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0097000000-3e67e2b99b64bbb19dde2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0749000000-4e378b170e7e0e501a172021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002f-3911000000-3d55560ae9987134faeb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-0900000000-1206f2feee3fa74b86742021-09-24View Spectrum
NMRNot Available
ChemSpider ID92280
ChEMBL IDCHEMBL259548
KEGG Compound IDC14475
Pubchem Compound ID102146
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01471
HMDB IDHMDB06048
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference