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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-20 06:57:58 UTC
HMDB IDHMDB0000365
Secondary Accession Numbers
  • HMDB00365
Metabolite Identification
Common NameEpiandrosterone
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 ).
Structure
Thumb
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-oneCAS
3β-AndrosteroneCAS
3β-Hydroxy-17-oxo-5α-androstaneCAS
3β-Hydroxy-5α-androstan-17-oneCAS
3β-Hydroxy-5α-androstane-17-oneCAS
3β-Hydroxyandrostan-17-oneCAS
3β-Hydroxyetioallocholan-17-oneCAS
3β-OH-5α-Androstane-17-oneCAS
5α-Androstan-17-one-3β-olCAS
5α-Androstan-3β-ol-17-oneCAS
5α-Androstane-3β-ol-17-oneCAS
(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 Weight290.4403
Monoisotopic Molecular Weight290.224580204
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
CAS Registry Number481-29-8
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=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
DescriptionThis compound 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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point178 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.02 mg/mL at 23 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0063 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 RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0390000000-17f2f9f14aa5e282a19aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0f7k-1139000000-2bff067a4137502d6ea7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-0190000000-b665b61b3fc9060b35b5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-4900000000-e43c3bdb0c139ec15f8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9300000000-c77bd97ae174005bf348View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0090000000-fb385ad40b5d4ae1a6d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-0290000000-6287ec557af150ef07feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-3690000000-da6f3211b1e397dcf1aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-03f14a475acfab5558d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-5e4902f7af7820145954View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06xx-2090000000-97cca29f0df7b3cc3714View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Adipose Tissue
  • Adrenal Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.9 (2.65-4.19) uMAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Male
Schizophrenia
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Schizophrenia
  1. Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021984
KNApSAcK IDNot Available
Chemspider ID9230560
KEGG Compound IDC07635
BioCyc IDNot Available
BiGG ID45201
Wikipedia LinkEpiandrosterone
METLIN IDNot Available
PubChem Compound11055399
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceJohnson, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:15954157 ]
  2. 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. [PubMed:15650074 ]
  3. Johnson MD, Bebb RA, Sirrs SM: Uses of DHEA in aging and other disease states. Ageing Res Rev. 2002 Feb;1(1):29-41. [PubMed:12039447 ]
  4. 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. [PubMed:6330917 ]
  5. 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. [PubMed:16040239 ]
  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. [PubMed:8476769 ]
  7. Matsuzaki Y, Honda A: Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents. Curr Pharm Des. 2006;12(26):3411-21. [PubMed:17017935 ]
  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. [PubMed:12475725 ]
  9. Chalbot S, Morfin R: Neurosteroids: metabolism in human intestine microsomes. Steroids. 2005 Apr;70(4):319-26. [PubMed:15784286 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325