Epitestosterone (CHEM016526)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:35:56 UTC
Update Date2016-11-09 01:15:25 UTC
Accession NumberCHEM016526
Identification
Common NameEpitestosterone
ClassSmall Molecule
DescriptionAn androstanoid that is the C-17 epimer of testosterone.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Epi-testosteroneChEBI
17-EpitestosteroneHMDB
17a-cis-TestosteroneHMDB
cis-TestosteroneHMDB
IsotestosteroneHMDB
17-alpha-TestosteroneHMDB
17 alpha TestosteroneHMDB
EpitestosteroneMeSH, HMDB
Chemical FormulaC19H28O2
Average Molecular Mass288.424 g/mol
Monoisotopic Mass288.209 g/mol
CAS Registry Number481-30-1
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
SMILES[H][C@@]12CC[C@@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=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
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 Solubility0.033 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-1940000000-716f44b32e61cf34c7b4Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-006t-1940000000-716f44b32e61cf34c7b4Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-004i-3910000000-d6ace9b7f8aff4dd46d0Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-053u-1920200000-db3504f562c54e6e1bbbSpectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-004l-3910000000-b43cd1ee268a855c8aa0Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-004l-3910000000-356ddfa8ddf8e551278dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0597-7920000000-dde7fba02fcbcec2d665Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05fs-4920000000-ccd839134de79f179f9eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00ds-0950000000-c65fc8043083ad93d169Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004i-3910000000-d6ace9b7f8aff4dd46d0Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053u-1920200000-db3504f562c54e6e1bbbSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-b43cd1ee268a855c8aa0Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-004l-3910000000-356ddfa8ddf8e551278dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-074i-0390000000-09e2a725ebd92c93dc88Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000t-1119000000-bf66038b9de80f6b8aabSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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)splash10-000i-0090000000-e1af5f6bcaf571731a2bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052b-7900000000-581eb9c19ccb29ebac52Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-052b-9300000000-37c235bd069ce0c93813Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0690-0190000000-d4814fdc14f2b2818eb2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0fk9-1690000000-b39908a52b06c7853085Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0950000000-5ee2f8e5795ea913ebadSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-f4e3ff2bfc8e41de9c54Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-3b8123363e31bc461acfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0190000000-4b469479ef097f60ed90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0390000000-8bebba5f70c72e80b630Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5890000000-46ba5a59d051001f2a63Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-3c963477109db1f6b39eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-87d4a2534cd39e8c54a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-1190000000-abbd0808a06f67c1f6fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy0-0090000000-9f1b0a9f20aee057d1ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-7add27947ecc7b5b14bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ki-0960000000-98c9b1c540f6d162d225Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-2900000000-f5717697f5b4e8b7505fSpectrum
MSMass Spectrum (Electron Ionization)splash10-00dv-5940000000-5e22fba0c369374c75dfSpectrum
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 IDDB07768
HMDB IDHMDB0000628
FooDB IDFDB011544
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5601
PDB IDNot Available
Wikipedia LinkEpitestosterone
Chemspider ID9789
ChEBI ID42534
PubChem Compound ID10204
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDM2MDB005065
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22956306
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23263519
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24333796
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2532272
5. Alvarez, Francisco. Steroids. CCXLIX. A new synthesis of epitestosterone from pregnenolone acetate via nitrosation. Steroids (1963), 2(4), 393-8.
6. 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.
7. 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.
8. 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.
9. Starka L: Epitestosterone. J Steroid Biochem Mol Biol. 2003 Oct;87(1):27-34.
10. 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.
11. Aguilera R, Hatton CK, Catlin DH: Detection of epitestosterone doping by isotope ratio mass spectrometry. Clin Chem. 2002;48(4):629-36.
12. 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.
13. 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.
14. Yamamoto Y, Peric-Golia P, Osawa Y, Kirdani RY, Sanberg AA: Androgen metabolism in sheep. Steroids. 1978 Oct;32(3):373-88.
15. 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.
16. 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.