Epiandrosterone (CHEM034821)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:15:07 UTC
Update Date2016-11-09 01:21:11 UTC
Accession NumberCHEM034821
Identification
Common NameEpiandrosterone
ClassSmall Molecule
DescriptionEpiandrosterone is a naturally occurring steroid synthesized in the adrenal cortex, gonads, brain, and gastrointestinal tract. It is less active than androsterone and excreted in small amounts in normal human urine. Epiandrosterone is a metabolite of the most abundant adrenal androgenic steroid dehydroepiandrosterone (DHEA) in young adult humans, but is not completely inactive and is considered an effector as well. Epiandrosterone is a precursor or substrate for cytochrome P450 species and enzymes (EC 1.14.13.100, 25-hydroxycholesterol 7alpha-hydroxylase) that produce 7alpha- and 7beta-hydroxylated metabolites in the human brain and other organs. These 7-hydroxylated derivatives exert anti-glucocorticoid and neuroprotective effects. (PMID: 17017935, 12475725, 15650074, 15784286) [HMDB]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-EpiandrosteroneHMDB
3b-AndrosteroneHMDB
3b-Hydroxy-17-oxo-5a-androstaneHMDB
3b-Hydroxy-5a-androstan-17-oneHMDB
3b-Hydroxy-5a-androstane-17-oneHMDB
3b-Hydroxyandrostan-17-oneHMDB
3b-Hydroxyetioallocholan-17-oneHMDB
3b-OH-5a-Androstane-17-oneHMDB
5a-Androstan-3b-ol-17-oneHMDB
5a-Androstane-3b-ol-17-oneHMDB
D-EpiandrosteroneHMDB
Epi-andosteroneHMDB
Epi-androsteroneHMDB
Iso-androsteroneHMDB
IsoandrosteroneHMDB
trans-AndrosteroneHMDB
(3Β,5α)-3-hydroxyandrostan-17-oneHMDB
3Β-androsteroneHMDB
3Β-hydroxy-17-oxo-5α-androstaneHMDB
3Β-hydroxy-5α-androstan-17-oneHMDB
3Β-hydroxy-5α-androstane-17-oneHMDB
3Β-hydroxyandrostan-17-oneHMDB
3Β-hydroxyetioallocholan-17-oneHMDB
3Β-OH-5α-androstane-17-oneHMDB
5Α-androstan-17-one-3β-olHMDB
5Α-androstan-3β-ol-17-oneHMDB
5Α-androstane-3β-ol-17-oneHMDB
(3beta,5alpha)-3-Hydroxyandrostan-17-oneHMDB
3beta-AndrosteroneHMDB
3beta-Hydroxy-17-oxo-5alpha-androstaneHMDB
3beta-Hydroxy-5alpha-androstan-17-oneHMDB
3beta-Hydroxy-5alpha-androstane-17-oneHMDB
3beta-Hydroxyandrostan-17-oneHMDB
3beta-Hydroxyetioallocholan-17-oneHMDB
3beta-OH-5alpha-Androstane-17-oneHMDB
5alpha-Androstan-17-one-3beta-olHMDB
5alpha-Androstan-3beta-ol-17-oneHMDB
5alpha-Androstane-3beta-ol-17-oneHMDB
Chemical FormulaC19H30O2
Average Molecular Mass290.440 g/mol
Monoisotopic Mass290.225 g/mol
CAS Registry Number481-29-8
IUPAC Name(1S,2S,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
Traditional Name(1S,2S,5S,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])CCC2C[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-QRIARFFBSA-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-beta-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 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 Solubility0.0064 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
Polarizability34.7 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, Positivesplash10-03ea-0390000000-17f2f9f14aa5e282a19aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0f7k-1139000000-2bff067a4137502d6ea7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 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 - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-0190000000-b665b61b3fc9060b35b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-4900000000-e43c3bdb0c139ec15f8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9300000000-c77bd97ae174005bf348Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0090000000-fb385ad40b5d4ae1a6d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-0290000000-6287ec557af150ef07feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-3690000000-da6f3211b1e397dcf1aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-03f14a475acfab5558d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-5e4902f7af7820145954Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06xx-2090000000-97cca29f0df7b3cc3714Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-afb176951034ef62419fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052e-0930000000-1ed776267953f7acda8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4j-2900000000-1ba60805778f2942bfd7Spectrum
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
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
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 IDHMDB0000365
FooDB IDFDB021984
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID45201
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEpiandrosterone
Chemspider ID9230560
ChEBI IDNot Available
PubChem Compound ID11055399
Kegg Compound IDC07635
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Johnson, Wm. S.; Bannister, Brian; Pappo, Raphael. Steroid total synthesis-hydrochrysene approach. VII. Metal-in-ammonia reduction of the aromatic nucleus. dl-Epiandrosterone and the lumi epimer. Journal of the American Chemical Society (1956), 78 6331-9.
2. Johnson MD, Bebb RA, Sirrs SM: Uses of DHEA in aging and other disease states. Ageing Res Rev. 2002 Feb;1(1):29-41.
3. Norman RJ, Maharaj C, Adhikari M, Joubert SM: Adrenal sensitivity to adrenocorticotrophin in twin neonates--effect of birth order and growth retardation. S Afr Med J. 1984 Jul 21;66(3):90-2.
4. 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.
5. 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.
6. Thijssen JH, Daroszewski J, Milewicz A, Blankenstein MA: Local aromatase activity in human breast tissues. J Steroid Biochem Mol Biol. 1993 Mar;44(4-6):577-82.
7. Matsuzaki Y, Honda A: Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents. Curr Pharm Des. 2006;12(26):3411-21.
8. Yoshida S, Honda A, Matsuzaki Y, Fukushima S, Tanaka N, Takagiwa A, Fujimoto Y, Miyazaki H, Salen G: Anti-proliferative action of endogenous dehydroepiandrosterone metabolites on human cancer cell lines. Steroids. 2003 Jan;68(1):73-83.
9. Chalbot S, Morfin R: Human liver S9 fractions: metabolism of dehydroepiandrosterone, epiandrosterone, and related 7-hydroxylated derivatives. Drug Metab Dispos. 2005 Apr;33(4):563-9. Epub 2005 Jan 13.
10. Chalbot S, Morfin R: Neurosteroids: metabolism in human intestine microsomes. Steroids. 2005 Apr;70(4):319-26.