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Showing Compound Mesterolone (FDB023812)

Record Information
Version1.0
Creation date2011-09-21 00:35:04 UTC
Update date2015-07-21 06:57:52 UTC
Primary IDFDB023812
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMesterolone
DescriptionMesterolone is a synthetic anabolic androgenic steroid (AAS) with reported abuses in human sports. As for other AAS, mesterolone is also a potential doping agent in equine sports. In humans, mesterolone exhibits no inhibitory effects on hypophysial gonadotropin secretion or on spermatogenesis, unlike most androgens. Mesterolone has been used in the treatment of primary nocturnal enuresis in boys six to ten years of age. Mesterolone probably modulates the autonomic innervation of the vesical musculature with correction of the defective neural mechanism which is believed to be implicated in the pathogenesis of nocturnal enuresis. Mesterolone has been utilized in hypogonadism patients to increase total ejaculation volume and the concentration of fructose in the spermatic plasma to normal levels. Mesterolone treatment decreases cholesterol, beta-lipoproteins, fatty acid esters, free fatty acids, triglycerides and glycerol in human serum. (PMID: 4880965, 17616252, 10796496, 17636603, 2087834, 6111418, 6142498, 6386424, 7558381, 792898) [HMDB]
CAS Number1424-00-6
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0064 g/LALOGPS
logP3.75ALOGPS
logP3.7ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.15 m³·mol⁻¹ChemAxon
Polarizability36.46 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O2
IUPAC name(1S,2S,3S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
InChI IdentifierInChI=1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1
InChI KeyUXYRZJKIQKRJCF-TZPFWLJSSA-N
Isomeric SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)C[C@H](C)[C@]12C
Average Molecular Weight304.4669
Monoisotopic Molecular Weight304.240230268
Classification
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-oxosteroid
  • 3-oxo-5-alpha-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSMesterolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03g1-0290000000-6711f2fd4cedd8b8ebe9Spectrum
Predicted GC-MSMesterolone, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dj-2029000000-d49394c5377c1d882480Spectrum
Predicted GC-MSMesterolone, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0195000000-44dcd42d89336ba3b7502017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0291000000-412b4cbbe59f184a654f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052o-1790000000-09c00b6e9a55d7df23002017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-e48e22f298cdef5479312017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0059000000-231f9da9a32e84b9b6042017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007c-3090000000-69a7d162e0bb3918d70b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-f9d10b76ade80bd401ad2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-f9d10b76ade80bd401ad2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udj-0094000000-7cb92f7f18ba376864182021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0079000000-2860312a6cf9370e19572021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0960000000-9c3e64e51c3a7c290a002021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3910000000-a9991caf02a89a9820902021-09-24View Spectrum
NMRNot Available
ChemSpider ID14296
ChEMBL IDCHEMBL258918
KEGG Compound IDD04947
Pubchem Compound ID15020
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06036
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMesterolone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference