Androsterone (CHEM017470)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:23:03 UTC
Update Date2016-11-09 01:15:36 UTC
Accession NumberCHEM017470
Identification
Common NameAndrosterone
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3alpha,5alpha)-3-Hydroxyandrostan-17-oneChEBI
3-Epihydroxyetioallocholan-17-oneChEBI
3alpha-Hydroxy-5alpha-androstan-17-oneChEBI
3alpha-Hydroxyetioallocholan-17-oneChEBI
5alpha-Androstane-3alpha-ol-17-oneChEBI
5alpha-AndrosteroneChEBI
AndrokinineChEBI
AndrotineChEBI
cis-AndrosteroneChEBI
(3a,5a)-3-Hydroxyandrostan-17-oneGenerator
(3Α,5α)-3-hydroxyandrostan-17-oneGenerator
3a-Hydroxy-5a-androstan-17-oneGenerator
3Α-hydroxy-5α-androstan-17-oneGenerator
3a-Hydroxyetioallocholan-17-oneGenerator
3Α-hydroxyetioallocholan-17-oneGenerator
5a-Androstane-3a-ol-17-oneGenerator
5Α-androstane-3α-ol-17-oneGenerator
5a-AndrosteroneGenerator
5Α-androsteroneGenerator
3-alpha-Hydroxy-5-alpha-androstan-17-oneHMDB
3 alpha Hydroxy 5 alpha androstan 17 oneHMDB
5 alpha Androstan 3 alpha ol 17 oneHMDB
5 alpha-Androstan-3 alpha-ol-17-oneHMDB
EpiandrosteroneHMDB
3-alpha-Hydroxy-17-androstanoneHMDB
3-alpha-Hydroxy-5-alpha-androstane-17-oneHMDB
3-alpha-Hydroxy-5alpha-androstan-17-oneHMDB
3-alpha-Hydroxyetioallocholan-17-oneHMDB
3-Hydroxy-(3-alpha,5-alpha)-androstan-17-oneHMDB
3-Hydroxyandrostan-17-oneHMDB
3alpha-Hydroxy-17-androstanoneHMDB
5-alpha-Androstan-3-alpha-ol-17-oneHMDB
5-alpha-Androstane-3alpha-ol-17-oneHMDB
5-alpha-AndrosteroneHMDB
Androstanon-3-alpha-ol-17-oneHMDB
Atromide iciHMDB
3Α-hydroxy-17-androstanoneHMDB
3Α-hydroxy-5α-androstane-17-oneHMDB
5Α-androstan-17-one-3α-olHMDB
5Α-androstan-3α-ol-17-oneHMDB
3alpha-Hydroxy-5alpha-androstane-17-oneHMDB
5alpha-Androstan-17-one-3alpha-olHMDB
5alpha-Androstan-3alpha-ol-17-oneHMDB
AndrosteroneHMDB
Chemical FormulaC19H30O2
Average Molecular Mass290.440 g/mol
Monoisotopic Mass290.225 g/mol
CAS Registry Number53-41-8
IUPAC Name(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
Traditional Name(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@]([H])(O)CC[C@]12C
InChI IdentifierInChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1
InChI KeyQGXBDMJGAMFCBF-HLUDHZFRSA-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-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • 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 Solubility0.0064 g/LALOGPS
logP3.71ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.81 m³·mol⁻¹ChemAxon
Polarizability34.56 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-056u-6920000000-1d886b76fe1f65860afbSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-00al-9820000000-321baddda5ac4f8adaa7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0536-7900000000-8cce10a8e140584407c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-fbea13833f57d0820cd8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-052r-6490000000-d9f8bf6f9bc4664ccad2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-f56a880ba97983c7e021Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0bta-0930000000-49751ee4f183943f62faSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-f81b1315d55db1d47ec4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-001c-7190000000-e870cf89a876e5f81d31Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0390000000-85c48da18cebca66ba3cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 55V, Positivesplash10-00di-0090000000-4a8b942c855c02555969Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0bta-0930000000-078d7455103eab0cf1eeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0390000000-905b691e9dad87bc603cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-0090000000-514df1ac9844abce75a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-1930000000-b9c49a039799b0a23e04Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-08gj-0900000000-9f326ea5c1c454997fd3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-02cv-0900000000-9d78808dd524e4ca6c50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0090000000-42eb8c941695a061666dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-0290000000-1a37c17eb6ea7be9211cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06u7-2790000000-d6e7cebd4af538181f77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-9e9f9de3b33af0311acdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-5ba62f51f815ded16002Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-2190000000-513ad65531fff88b9f69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-c8c452fd99c6bb4f3631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-c8c452fd99c6bb4f3631Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0090000000-00c0e7de4e528b98df5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-afb176951034ef62419fSpectrum
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 IDNot Available
HMDB IDHMDB0000031
FooDB IDFDB021881
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID35244
BioCyc IDNot Available
METLIN ID2797
PDB IDNot Available
Wikipedia LinkAndrosterone
Chemspider ID5668
ChEBI ID16032
PubChem Compound ID5879
Kegg Compound IDC00523
YMDB IDNot Available
ECMDB IDECMDB24015
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Marker, Russell E. Androsterone. Journal of the American Chemical Society (1935), 57 1755-6.
2. Muller L, Phillipou G: Quantification of 5 alpha- and 5 beta-androstanediols in urine by gas chromatography-mass spectrometry. Clin Chem. 1987 Feb;33(2 Pt 1):256-60.
3. Schonberger W, Benes P, Morsches B, Zabel B, Scheidt E: [Improvement in the longitudinal growth in Ullrich-Turner syndrome with oxandrolone. Function of urinary excretion of steroid hormones]. Dtsch Med Wochenschr. 1982 Jul 2;107(26):1008-11.
4. Kim YS, Zhang H, Kim HY: Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. Anal Biochem. 2000 Jan 15;277(2):187-95.
5. Labows JN, Preti G, Hoelzle E, Leyden J, Kligman A: Steroid analysis of human apocrine secretion. Steroids. 1979 Sep;34(3):249-58.
6. Raju U, Kadner S, Levitz M, Kaganowicz A, Blaustein A: Glucosiduronidation and esterification of androsterone by human breast tumors in vitro. Steroids. 1981 Apr;37(4):399-407.
7. Kaminski RM, Marini H, Kim WJ, Rogawski MA: Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. 2005 Jun;46(6):819-27.
8. Grosse J, Anielski P, Hemmersbach P, Lund H, Mueller RK, Rautenberg C, Thieme D: Formation of 19-norsteroids by in situ demethylation of endogenous steroids in stored urine samples. Steroids. 2005 Jul;70(8):499-506. Epub 2005 Mar 29.
9. Toth I, Faredin I: Steroids excreted by human skin. II. C19-steroid sulphates in human axillary sweat. Acta Med Hung. 1985;42(1-2):21-8.
10. Teller WM, Homoki J, Wudy S, Schlickenrieder JH: Adrenarche is dissociated from gonadarche--studies in patients with Turner's syndrome. Acta Endocrinol Suppl (Copenh). 1986;279:232-40.
11. Mitamura K, Setaka M, Shimada K, Honma S, Namiki M, Koh E, Mizokami A: Determination of sulfates of androsterone and epiandrosterone in human serum using isotope diluted liquid chromatography-electrospray ionization-mass spectrometry. Biomed Chromatogr. 2005 Dec;19(10):796-801.
12. Tchedam Ngatcha B, Luu-The V, Labrie F, Poirier D: Androsterone 3alpha-ether-3beta-substituted and androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: chemical synthesis and structure-activity relationship. J Med Chem. 2005 Aug 11;48(16):5257-68.
13. Hammond GL: Endogenous steroid levels in the human prostate from birth to old age: a comparison of normal and diseased tissues. J Endocrinol. 1978 Jul;78(1):7-19.
14. Biswas MG, Russell DW: Expression cloning and characterization of oxidative 17beta- and 3alpha-hydroxysteroid dehydrogenases from rat and human prostate. J Biol Chem. 1997 Jun 20;272(25):15959-66.
15. Matsuzaki Y, Honda A: Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents. Curr Pharm Des. 2006;12(26):3411-21.
16. Belanger A, Pelletier G, Labrie F, Barbier O, Chouinard S: Inactivation of androgens by UDP-glucuronosyltransferase enzymes in humans. Trends Endocrinol Metab. 2003 Dec;14(10):473-9.
17. Barbier O, Belanger A: The cynomolgus monkey (Macaca fascicularis) is the best animal model for the study of steroid glucuronidation. J Steroid Biochem Mol Biol. 2003 Jun;85(2-5):235-45.
18. Belanger A, Hum DW, Beaulieu M, Levesque E, Guillemette C, Tchernof A, Belanger G, Turgeon D, Dubois S: Characterization and regulation of UDP-glucuronosyltransferases in steroid target tissues. J Steroid Biochem Mol Biol. 1998 Apr;65(1-6):301-10.
19. Thevis M, Geyer H, Mareck U, Sigmund G, Henke J, Henke L, Schanzer W: Detection of manipulation in doping control urine sample collection: a multidisciplinary approach to determine identical urine samples. Anal Bioanal Chem. 2007 Aug;388(7):1539-43. Epub 2007 Jan 27.
20. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
21. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
22. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
23. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
24. The lipid handbook with CD-ROM
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=10438974
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=19493957
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=24705905