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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:04 UTC
HMDB IDHMDB0000628
Secondary Accession Numbers
  • HMDB00628
Metabolite Identification
Common NameEpitestosterone
DescriptionEpitestosterone, or isotestosterone, also known as 17alpha-testosterone or as androst-4-en-17alpha-ol-3-one belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. Epitestosterone is an endogenous steroid and a C-17 epimer of the androgen sex hormone testosterone. It is a weak competitive antagonist of the androgen receptor (AR) and a potent 5alpha-reductase inhibitor. Structurally, epitestosterone differs from testosterone only in the configuration at the hydroxy-bearing carbon, C17. Epitestosterone is believed to form in a similar way to testosterone with 50% of epitestosterone production in human males taking place in the testis. Epitestosterone levels are typically highest in young males; however, by adulthood, most healthy males exhibit a testosterone to epitestosterone ratio (T/E ratio) of about 1:1 (PMID: 11901061 ). A study of Australian athletes found that the mean T/E ratio in the study was 1.15:1. Another study found that the max T/E ratio for the 95th percentile of athletes was 3.71:1, and the max T/E ratio for the 99th percentile was 5.25:1. Epitestosterone has not been shown to enhance athletic performance, although administration of epistestosterone can be used to mask a high level of testosterone if the standard T/E ratio test is used. As such, epitestosterone is banned by many sporting authorities as a masking agent for testosterone. Interestingly, small amounts of ethanol can elevate T/E values, with women being more susceptible (PMID: 28671321 ).
Structure
Data?1582752145
Synonyms
ValueSource
Epi-testosteroneChEBI
17-EpitestosteroneHMDB
17a-cis-TestosteroneHMDB
cis-TestosteroneHMDB
IsotestosteroneHMDB
17-alpha-TestosteroneHMDB
17 alpha TestosteroneHMDB
EpitestosteroneMeSH, HMDB
Chemical FormulaC19H28O2
Average Molecular Weight288.4244
Monoisotopic Molecular Weight288.20893014
IUPAC Name(1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10R,11S,14R,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
CAS Registry Number481-30-1
SMILES
[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O2/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/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17+,18-,19-/m0/s1
InChI KeyMUMGGOZAMZWBJJ-KZYORJDKSA-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
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Cyclic ketone
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.033 g/LALOGPS
logP2.99ALOGPS
logP3.37ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.43 m³·mol⁻¹ChemAxon
Polarizability33.93 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]+171.35531661259
DarkChem[M-H]-168.19431661259
AllCCS[M+H]+174.27732859911
AllCCS[M-H]-178.5132859911
DeepCCS[M-2H]-205.28830932474
DeepCCS[M+Na]+179.34330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Epitestosterone[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C3544.2Standard polar33892256
Epitestosterone[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C2567.6Standard non polar33892256
Epitestosterone[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C2768.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Epitestosterone,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@H]2O[Si](C)(C)C2764.5Semi standard non polar33892256
Epitestosterone,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@H]2O2636.1Semi standard non polar33892256
Epitestosterone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@H]2O[Si](C)(C)C2694.5Semi standard non polar33892256
Epitestosterone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@H]2O[Si](C)(C)C2693.2Standard non polar33892256
Epitestosterone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC[C@H]2O[Si](C)(C)C2974.7Standard polar33892256
Epitestosterone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C3021.3Semi standard non polar33892256
Epitestosterone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@@H](O)[C@@]3(C)CC[C@@H]122917.7Semi standard non polar33892256
Epitestosterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123233.8Semi standard non polar33892256
Epitestosterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123170.2Standard non polar33892256
Epitestosterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC[C@@H](O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123231.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Epitestosterone EI-B (Non-derivatized)splash10-006t-1940000000-716f44b32e61cf34c7b42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone EI-B (Non-derivatized)splash10-006t-1940000000-716f44b32e61cf34c7b42018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone GC-MS (1 TMS)splash10-004i-3910000000-d6ace9b7f8aff4dd46d02018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone GC-MS (2 TMS)splash10-053u-1920200000-db3504f562c54e6e1bbb2018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone GC-MS (1 MEOX; 1 TMS)splash10-004l-3910000000-b43cd1ee268a855c8aa02018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone GC-MS (1 MEOX; 1 TMS)splash10-004l-3910000000-356ddfa8ddf8e551278d2018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone EI-B (Non-derivatized)splash10-0597-7920000000-dde7fba02fcbcec2d6652018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone EI-B (Non-derivatized)splash10-05fs-4920000000-ccd839134de79f179f9e2018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone EI-B (Non-derivatized)splash10-00ds-0950000000-c65fc8043083ad93d1692018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized)splash10-004i-3910000000-d6ace9b7f8aff4dd46d02018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized)splash10-053u-1920200000-db3504f562c54e6e1bbb2018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized)splash10-004l-3910000000-b43cd1ee268a855c8aa02018-05-25HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized)splash10-004l-3910000000-356ddfa8ddf8e551278d2018-05-25HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized) - 70eV, Positivesplash10-074i-0390000000-09e2a725ebd92c93dc882017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epitestosterone GC-MS (1 TMS) - 70eV, Positivesplash10-000t-1119000000-bf66038b9de80f6b8aab2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epitestosterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epitestosterone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epitestosterone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Epitestosterone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dv-5940000000-5e22fba0c369374c75df2018-05-25Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Epitestosterone Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0090000000-e1af5f6bcaf571731a2b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epitestosterone Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-052b-7900000000-581eb9c19ccb29ebac522012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epitestosterone Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-052b-9300000000-37c235bd069ce0c938132012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epitestosterone Linear Ion Trap , negative-QTOFsplash10-0690-0190000000-d4814fdc14f2b2818eb22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epitestosterone Linear Ion Trap , positive-QTOFsplash10-0fk9-1690000000-b39908a52b06c78530852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epitestosterone 20V, Positive-QTOFsplash10-0a4r-0950000000-5ee2f8e5795ea913ebad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epitestosterone 10V, Positive-QTOFsplash10-000i-0190000000-f4e3ff2bfc8e41de9c542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Epitestosterone 40V, Positive-QTOFsplash10-0a4i-0900000000-3b8123363e31bc461acf2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 10V, Positive-QTOFsplash10-00dr-0190000000-4b469479ef097f60ed902017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 20V, Positive-QTOFsplash10-00dr-0390000000-8bebba5f70c72e80b6302017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 40V, Positive-QTOFsplash10-0udi-5890000000-46ba5a59d051001f2a632017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 10V, Negative-QTOFsplash10-000i-0090000000-3c963477109db1f6b39e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 20V, Negative-QTOFsplash10-000i-0090000000-87d4a2534cd39e8c54a82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 40V, Negative-QTOFsplash10-0abc-1190000000-abbd0808a06f67c1f6fc2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 10V, Negative-QTOFsplash10-000i-0090000000-383f8ad782110ec64fbf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 20V, Negative-QTOFsplash10-000i-0090000000-383f8ad782110ec64fbf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 40V, Negative-QTOFsplash10-0uy0-0090000000-9f1b0a9f20aee057d1dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 10V, Positive-QTOFsplash10-000i-0090000000-7add27947ecc7b5b14bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 20V, Positive-QTOFsplash10-03ki-0960000000-98c9b1c540f6d162d2252021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Epitestosterone 40V, Positive-QTOFsplash10-0bt9-2900000000-f5717697f5b4e8b7505f2021-09-23Wishart 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)
Biospecimen Locations
  • Blood
Tissue Locations
  • Adrenal Gland
  • Ovary
  • Prostate
  • Testis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00132 +/- 0.00008 uMAdult (>18 years old)MaleEugonadism details
BloodDetected and Quantified0.00068 +/- 0.00004 uMAdult (>18 years old)MaleHypogonadism details
Associated Disorders and Diseases
Disease References
Hypogonadism
  1. Kicman AT, Coutts SB, Cowan DA, Handelsman DJ, Howe CJ, Burring S, Wu FC: Adrenal and gonadal contributions to urinary excretion and plasma concentration of epitestosterone in men--effect of adrenal stimulation and implications for detection of testosterone abuse. Clin Endocrinol (Oxf). 1999 May;50(5):661-8. [PubMed:10468933 ]
Associated OMIM IDs
DrugBank IDDB07768
Phenol Explorer Compound IDNot Available
FooDB IDFDB011544
KNApSAcK IDNot Available
Chemspider ID9789
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEpitestosterone
METLIN ID5601
PubChem Compound10204
PDB IDNot Available
ChEBI ID42534
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAlvarez, Francisco. Steroids. CCXLIX. A new synthesis of epitestosterone from pregnenolone acetate via nitrosation. Steroids (1963), 2(4), 393-8.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Falk O, Palonek E, Bjorkhem I: Effect of ethanol on the ratio between testosterone and epitestosterone in urine. Clin Chem. 1988 Jul;34(7):1462-4. [PubMed:3390919 ]
  2. Kicman AT, Oftebro H, Walker C, Norman N, Cowan DA: Potential use of ketoconazole in a dynamic endocrine test to differentiate between biological outliers and testosterone use by athletes. Clin Chem. 1993 Sep;39(9):1798-803. [PubMed:8375050 ]
  3. Riondino G, Strollo F: [Age-dependent changes in epitestosterone urinary excretion in man]. Boll Soc Ital Biol Sper. 1981 Nov 30;57(22):2215-21. [PubMed:7326107 ]
  4. Starka L: Epitestosterone. J Steroid Biochem Mol Biol. 2003 Oct;87(1):27-34. [PubMed:14630088 ]
  5. Marenich LP: [Effect of chorionic gonadotropin on the urinary excretion of testosterone and other androgens in healthy men and those with coronary arteriosclerosis]. Kardiologiia. 1979 Jun;19(6):76-9. [PubMed:156806 ]
  6. Aguilera R, Hatton CK, Catlin DH: Detection of epitestosterone doping by isotope ratio mass spectrometry. Clin Chem. 2002;48(4):629-36. [PubMed:11901061 ]
  7. Bicikova M, Hampl R, Hill M, Starka L: Inhibition of steroid 17 alpha-hydroxylase and C17,20-lyase in the human testis by epitestosterone. J Steroid Biochem Mol Biol. 1993 Oct;46(4):515-8. [PubMed:8217882 ]
  8. Havlikova H, Hill M, Hampl R, Starka L: Sex- and age-related changes in epitestosterone in relation to pregnenolone sulfate and testosterone in normal subjects. J Clin Endocrinol Metab. 2002 May;87(5):2225-31. [PubMed:11994368 ]
  9. Yamamoto Y, Peric-Golia P, Osawa Y, Kirdani RY, Sanberg AA: Androgen metabolism in sheep. Steroids. 1978 Oct;32(3):373-88. [PubMed:715826 ]
  10. Kicman AT, Coutts SB, Cowan DA, Handelsman DJ, Howe CJ, Burring S, Wu FC: Adrenal and gonadal contributions to urinary excretion and plasma concentration of epitestosterone in men--effect of adrenal stimulation and implications for detection of testosterone abuse. Clin Endocrinol (Oxf). 1999 May;50(5):661-8. [PubMed:10468933 ]
  11. Albeiroti S, Ahrens BD, Sobolevskii T, Butch AW: The influence of small doses of ethanol on the urinary testosterone to epitestosterone ratio in men and women. Drug Test Anal. 2018 Mar;10(3):575-583. doi: 10.1002/dta.2241. Epub 2017 Aug 1. [PubMed:28671321 ]