Calusterone (CHEM035688)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:59:27 UTC
Update Date2016-11-09 01:21:21 UTC
Accession NumberCHEM035688
Identification
Common NameCalusterone
ClassSmall Molecule
DescriptionA 17-alkylated orally active androgenic steroid. A Schedule IV drug in Canada.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(7b,17b)-17-Hydroxy-7,17-dimethyl-androst-4-en-3-oneHMDB
17-beta-Hydroxy-7-beta,17-alpha-dimethylandrost-4-ene-3-oneHMDB
17-beta-Hydroxy-7-beta-17-dimethyl androst-4-en-3-oneHMDB
17-Dimethyl-17beta-hydroxy-7beta-androst-4-en-3-oneHMDB
17-Hydroxy-7,17-dimethylandrost-4-en-3-oneHMDB
17b-Hydroxy-7b,17-dimethyl-androst-4-en-3-oneHMDB
17b-Hydroxy-7b,17-dimethylandrost-4-en-3-oneHMDB
17beta-Dimethyl testosteroneHMDB
17beta-Hydroxy-7beta-17-dimethylandrost-4-en-3-oneHMDB
17beta-Hydroxy-7beta-17alpha-dimethylandrost-4-ene-3-oneHMDB
7-beta,17-alpha-Dimethyl testosteroneHMDB
7-beta,17-DimethyltestosteroneHMDB
7-beta-17-alpha-DimethyltestosteroneHMDB
7beta,17alpha-DimethyltestosteroneHMDB
7beta,17beta-DimethyltestosteroneHMDB
7beta-DimethyltestosteroneHMDB
CalusteronHMDB
CalusteronaHMDB
CalusteronumHMDB
DimethyltestosteroneHMDB
MethosarbHMDB
7 beta,17 alpha-DimethyltestosteroneMeSH, HMDB
Chemical FormulaC21H32O2
Average Molecular Mass316.478 g/mol
Monoisotopic Mass316.240 g/mol
CAS Registry Number17021-26-0
IUPAC Name(1S,2R,9S,10R,11S,14S,15S)-14-hydroxy-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Namecalusterone
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-/m0/s1
InChI KeyIVFYLRMMHVYGJH-PVPPCFLZSA-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 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 Solubility0.011 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
Polarizability37.77 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, 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
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
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 IDDB01564
HMDB IDHMDB0004627
FooDB IDFDB023386
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCalusterone
Chemspider ID26239
ChEBI ID554295
PubChem Compound ID28204
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Campbell, J. Allan; Babcock, John C. The synthesis of some 7a- and 7b-methyl steroid hormones. Journal of the American Chemical Society (1959), 81 4069-74.
2. Campbell, J. Allan; Babcock, John C. The synthesis of some 7a- and 7b-methyl steroid hormones. Journal of the American Chemical Society (1959), 81 4069-74.
3. Georgakopoulos CG, Vonaparti A, Stamou M, Kiousi P, Lyris E, Angelis YS, Tsoupras G, Wuest B, Nielen MW, Panderi I, Koupparis M: Preventive doping control analysis: liquid and gas chromatography time-of-flight mass spectrometry for detection of designer steroids. Rapid Commun Mass Spectrom. 2007;21(15):2439-46.
4. Marcos J, Pascual JA, de la Torre X, Segura J: Fast screening of anabolic steroids and other banned doping substances in human urine by gas chromatography/tandem mass spectrometry. J Mass Spectrom. 2002 Oct;37(10):1059-73.
5. Lloyd RE, Jones SE, Salmon SE: Comparative trial of low-dose adriamycin plus cyclophosphamide with or without additive hormonal therapy in advanced breast cancer. Cancer. 1979 Jan;43(1):60-5.
6. Choo HY, Kwon OS, Park J: Quantitative determination of stanozolol and its metabolite in urine by gas chromatography/mass spectrometry. J Anal Toxicol. 1990 Mar-Apr;14(2):109-12.