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Record Information
Version1.0
Creation Date2016-07-13 19:42:32 UTC
Update Date2016-09-23 18:44:42 UTC
LmdbLMDB00108
Secondary Accession NumbersNone
Metabolite Identification
Common NameTestosterone
DescriptionTestosterone is the most important androgen in potency and quantity. Testosterone is synthesized and released by the Leydig cells that lie between the tubules and comprise less than 5% of the total testicular volume. testosterone diffuses into the seminiferous tubules where it is essential for maintaining spermatogenesis. Some binds to an androgen-binding protein (ABP) that is produced by the Sertoli cells and is homologous to the sex-hormone binding globulin that transports testosterone in the general circulation. The ABP carries testosterone in the testicular fluid where it maintains the activity of the accessory sex glands and may also help to retain testosterone within the tubule and bind excess free hormone. Some testosterone is converted to estradiol by Sertoli cell-derived aromatase enzyme. Leydig cell steroidogenesis is controlled primarily by luteinizing hormone with negative feedback of testosterone on the hypothalamic-pituitary axis. The requirement of spermatogenesis for high local concentrations of testosterone means that loss of androgen production is likely to be accompanied by loss of spermatogenesis. Indeed, if testicular androgen production is inhibited by the administration of exogenous androgens then spermatogenesis ceases. This is the basis of using exogenous testosterone as a male contraceptive. testosterone is converted to dihydrotestosterone by 5a-reductase type 2 (EC 1.3.1.22, SRD5A2), the androgen with the highest affinity for the androgen receptor. SRD5A2 deficiency illustrates the importance of dihydrotestosterone for external virilization, as individuals with this condition have normal male internal structures but their external genitalia are of female appearance. There is now clear evidence that the animal fetal testis and also the fetal adrenal gland is capable of testosterone biosynthesis during the first trimester. Regardless of the source of androgen production, the target tissue responds by male sexual differentiation of the external genitalia by the end of the first trimester. It is clear that testicular damage may result in loss of testosterone production or the loss of spermatogenesis or both. Loss of androgen production results in hypogonadism, the symptoms of which reflect the functions of testosterone. Male hypogonadism is defined as failure of the testes to produce normal amounts of testosterone, combined with signs and symptoms of androgen deficiency. Systemic testosterone levels fall by about 1% each year in men. Therefore, with increasing longevity and the aging of the population, the number of older men with testosterone deficiency will increase substantially over the next several decades. Serum testosterone levels decrease progressively in aging men, but the rate and magnitude of decrease vary considerably. Approximately 1% of healthy young men have total serum testosterone levels below normal; in contrast, approximately 20% of healthy men over age 60 years have serum testosterone levels below normal. (PMID: 17904450 , 17875487 ).
Structure
Thumb
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 Number58-22-0
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-DYKIIFRCSA-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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
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
BioavailabilityYesChemAxon
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
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Follicular Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Follicular FluidDetected and Quantified0.0485 +/- 0.00347 uMNot AvailablePorcine details
SerumDetected and Quantified0.00167 uMNot AvailableBovine details
SerumDetected and Quantified0.00171 uMNot AvailableBovine details
SerumDetected and Quantified<0.00115 uMNot AvailableBovine details
SerumDetected and Quantified0.000675&0.00115 uMNot AvailableBovine details
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
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kazi M, Geraci SA, Koch CA: Considerations for the diagnosis and treatment of testosterone deficiency in elderly men. Am J Med. 2007 Oct;120(10):835-40. [17904450 ]
  2. Krone N, Hanley NA, Arlt W: Age-specific changes in sex steroid biosynthesis and sex development. Best Pract Res Clin Endocrinol Metab. 2007 Sep;21(3):393-401. [17875487 ]