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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:01 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
Data?1582752126
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 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
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
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.02 mg/mL at 23 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.23531661259
DarkChem[M-H]-162.80731661259
AllCCS[M+H]+175.46632859911
AllCCS[M-H]-178.96832859911
DeepCCS[M-2H]-205.13430932474
DeepCCS[M+Na]+179.6530932474
AllCCS[M+H]+175.532859911
AllCCS[M+H-H2O]+172.532859911
AllCCS[M+NH4]+178.332859911
AllCCS[M+Na]+179.132859911
AllCCS[M-H]-179.032859911
AllCCS[M+Na-2H]-179.232859911
AllCCS[M+HCOO]-179.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Epiandrosterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C2280.7Standard polar33892256
Epiandrosterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C2441.5Standard non polar33892256
Epiandrosterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2C[C@@H](O)CC[C@]12C2637.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Epiandrosterone,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2578.5Semi standard non polar33892256
Epiandrosterone,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CCC4C[C@@H](O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2579.0Semi standard non polar33892256
Epiandrosterone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2602.6Semi standard non polar33892256
Epiandrosterone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2511.5Standard non polar33892256
Epiandrosterone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2920.4Standard polar33892256
Epiandrosterone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C12818.4Semi standard non polar33892256
Epiandrosterone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C2849.6Semi standard non polar33892256
Epiandrosterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3134.5Semi standard non polar33892256
Epiandrosterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C2771.5Standard non polar33892256
Epiandrosterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3167.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Epiandrosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-03ea-0390000000-17f2f9f14aa5e282a19a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epiandrosterone GC-MS (1 TMS) - 70eV, Positivesplash10-0f7k-1139000000-2bff067a4137502d6ea72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epiandrosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epiandrosterone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epiandrosterone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epiandrosterone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Epiandrosterone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-05fr-0190000000-b665b61b3fc9060b35b52012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epiandrosterone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-4900000000-e43c3bdb0c139ec15f8b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epiandrosterone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-05mo-9300000000-c77bd97ae174005bf3482012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 10V, Positive-QTOFsplash10-00dl-0090000000-fb385ad40b5d4ae1a6d92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 20V, Positive-QTOFsplash10-00dm-0290000000-6287ec557af150ef07fe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 40V, Positive-QTOFsplash10-000t-3690000000-da6f3211b1e397dcf1ae2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 10V, Negative-QTOFsplash10-000i-0090000000-03f14a475acfab5558d62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 20V, Negative-QTOFsplash10-000i-0090000000-5e4902f7af78201459542017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 40V, Negative-QTOFsplash10-06xx-2090000000-97cca29f0df7b3cc37142017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 10V, Positive-QTOFsplash10-0006-0090000000-afb176951034ef62419f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 20V, Positive-QTOFsplash10-052e-0930000000-1ed776267953f7acda8a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 40V, Positive-QTOFsplash10-0a4j-2900000000-1ba60805778f2942bfd72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 10V, Negative-QTOFsplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 20V, Negative-QTOFsplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epiandrosterone 40V, Negative-QTOFsplash10-000i-0090000000-00c0e7de4e528b98df5c2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
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 QuantifiedNot QuantifiedAdult (>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 QuantifiedNot QuantifiedAdult (>18 years old)Male
Schizophrenia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
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 ]
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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