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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:40:10 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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available171.35531661259
DarkChem[M-H]-PredictedNot Available168.19431661259
AllCCS[M+H]+PredictedNot Available174.27732859911
AllCCS[M-H]-PredictedNot Available178.5132859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Epitestosterone,1TMS,#12764.5178https://arxiv.org/abs/1905.12712
Epitestosterone,1TMS,#22636.071https://arxiv.org/abs/1905.12712
Epitestosterone,1TBDMS,#13021.3396https://arxiv.org/abs/1905.12712
Epitestosterone,1TBDMS,#22917.7356https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-1940000000-716f44b32e61cf34c7b42017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-1940000000-716f44b32e61cf34c7b42018-05-18View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-3910000000-d6ace9b7f8aff4dd46d02018-05-25View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-053u-1920200000-db3504f562c54e6e1bbb2018-05-25View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-004l-3910000000-b43cd1ee268a855c8aa02018-05-25View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-004l-3910000000-356ddfa8ddf8e551278d2018-05-25View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0597-7920000000-dde7fba02fcbcec2d6652018-05-25View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fs-4920000000-ccd839134de79f179f9e2018-05-25View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ds-0950000000-c65fc8043083ad93d1692018-05-25View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-3910000000-d6ace9b7f8aff4dd46d02018-05-25View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053u-1920200000-db3504f562c54e6e1bbb2018-05-25View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-b43cd1ee268a855c8aa02018-05-25View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-356ddfa8ddf8e551278d2018-05-25View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-074i-0390000000-09e2a725ebd92c93dc882017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000t-1119000000-bf66038b9de80f6b8aab2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dv-5940000000-5e22fba0c369374c75df2018-05-25View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0090000000-e1af5f6bcaf571731a2b2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-7900000000-581eb9c19ccb29ebac522012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9300000000-37c235bd069ce0c938132012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0690-0190000000-d4814fdc14f2b2818eb22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0fk9-1690000000-b39908a52b06c78530852017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0950000000-5ee2f8e5795ea913ebad2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-f4e3ff2bfc8e41de9c542021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-3b8123363e31bc461acf2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0190000000-4b469479ef097f60ed902017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0390000000-8bebba5f70c72e80b6302017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5890000000-46ba5a59d051001f2a632017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-3c963477109db1f6b39e2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-87d4a2534cd39e8c54a82017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-1190000000-abbd0808a06f67c1f6fc2017-07-26View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCl3, predicted)2012-12-05View 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
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 ]