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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 22:35:49 UTC
Update Date2020-02-26 21:25:10 UTC
HMDB IDHMDB0004627
Secondary Accession Numbers
  • HMDB04627
Metabolite Identification
Common NameCalusterone
DescriptionCalusterone is an androgenic steroid. Calusterone induce given orally induce a marked decrease (between 30 and 70% depending on the dose) in the binding capacity of oestradiol-17beta to specific uterine receptors in vivo. As an androgen, calusterone has been used as a therapeutic agent in postmenopausal women with metastatic breast cancer; the addition of a potent hormonal agent to effective cytotoxic chemotherapy improves the results of treatment of women with metastatic breast cancer. Calusterone is tested in sport screening; fast and sensitive method for the comprehensive screening of anabolic agents and other banned doping substances using gas chromatography/tandem mass spectrometry (GC/MS/MS) with an external ionization ion trap mass spectrometer have been developed for the parent substances and their metabolites. (PMID: 17610244 , 12375280 , 153787 , 2325376 , 12375280 ).
Structure
Data?1582752309
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-DimethyltestosteroneHMDB
Chemical FormulaC21H32O2
Average Molecular Weight316.4776
Monoisotopic Molecular Weight316.240230268
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
CAS Registry Number17021-26-0
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-/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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point128 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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 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
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 IDDB01564
Phenol Explorer Compound IDNot Available
FooDB IDFDB023386
KNApSAcK IDNot Available
Chemspider ID26239
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCalusterone
METLIN IDNot Available
PubChem Compound28204
PDB IDNot Available
ChEBI ID554295
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceCampbell, 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.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:17610244 ]
  2. 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. [PubMed:12375280 ]
  3. 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. [PubMed:153787 ]
  4. 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. [PubMed:2325376 ]