Showing metabocard for Epitestosterone (BMDB0000628)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:33:50 UTC
Update Date2020-06-04 20:38:12 UTC
MCDB ID BMDB0000628
Secondary Accession Numbers
  • BMDB00628
Metabolite Identification
Common NameEpitestosterone
DescriptionTestosterone 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. Thus, testosterone is considered to be a steroid lipid molecule. Testosterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Testosterone exists in all living organisms, ranging from bacteria to humans. Testosterone participates in a number of enzymatic reactions, within cattle. In particular, Testosterone can be converted into 19-hydroxytestosterone; which is catalyzed by the enzyme cytochrome P450 19A1. In addition, Testosterone can be converted into androstenedione; which is catalyzed by the enzyme testosterone 17-beta-dehydrogenase 3. In cattle, testosterone is involved in the metabolic pathway called the androgen and estrogen metabolism pathway. Testosterone is a potentially toxic compound.
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 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbf2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-383f8ad782110ec64fbf2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uy0-0090000000-9f1b0a9f20aee057d1dd2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-7add27947ecc7b5b14bc2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ki-0960000000-98c9b1c540f6d162d2252021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-2900000000-f5717697f5b4e8b7505f2021-09-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-00dv-5940000000-5e22fba0c369374c75df2018-05-25View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.0003 uM details
Detected and Quantified0.0002 uM details
Detected and Quantified0.00034 uM details
HMDB IDHMDB0000628
DrugBank IDDB07768
Phenol Explorer Compound IDNot Available
FoodDB 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
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. Courant F, Antignac JP, Laille J, Monteau F, Andre F, Le Bizec B: Exposure assessment of prepubertal children to steroid endocrine disruptors. 2. Determination of steroid hormones in milk, egg, and meat samples. J Agric Food Chem. 2008 May 14;56(9):3176-84. doi: 10.1021/jf800096f. Epub 2008 Apr 16. [PubMed:18412364 ]