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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-04-12 20:33:51 UTC
Update Date2022-03-07 02:49:29 UTC
HMDB IDHMDB0006026
Secondary Accession Numbers
  • HMDB06026
Metabolite Identification
Common NameNorbolethone
DescriptionNorbolethone is a 19-nor anabolic steroid first synthesized in 1966. During the 1960s it was administered to humans in efficacy studies concerned with short stature and underweight conditions. It has never been reported by doping control laboratories prior to 2001. Norbolethone was identified in two urine samples from one athlete by matching the mass spectra and chromatographic retention times with those of a reference standard. The samples also contained at least one likely metabolite. The samples were also unusual because the concentrations of endogenous steroids were exceptionally low. Since norbolethone is not known to be marketed by any pharmaceutical company, a clandestine source of norbolethone may exist. Norbolethone matches the description for what is described as a "designer steroid." Androgenic anabolic steroids (AAS) are defined as natural, synthetic or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic and neuro-endocrine systems, the AAS have been extensively used in sports activities. (PMID: 12112254 ).
Structure
Data?1582752371
Synonyms
ValueSource
13-EHDPOMeSH
13-Ethyl-17-hydroxy-18,19-dinor-17-pregn-4-en-20-yn-3-oneMeSH
NorboletoneChEMBL, HMDB
(+/-)-13,17a-diethyl-17b-hydroxygon-4-en-3-oneHMDB
(+/-)-13-ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-3-oneHMDB
(+/-)-13b,17a-diethyl-17b-hydroxygon-4-en-3-oneHMDB
(+/-)-17a-ethyl-18-homo-19-nortestosteroneHMDB
(17a)-(+/-)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-en-3-oneHMDB
13-Ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-3-oneHMDB
DL-13,17a-Diethyl-17-hydroxygon-4-en-3-oneHMDB
DL-13,17a-Diethyl-17b-hydroxygon-4-en-3-oneHMDB
DL-17b-Hydroxy-13b,17a-diethylgon-4-en-3-oneHMDB
DL-NorbolethoneHMDB
GenabolHMDB
Wy 3475HMDB
Chemical FormulaC21H32O2
Average Molecular Weight316.4776
Monoisotopic Molecular Weight316.240230268
IUPAC Name(1S,2R,10R,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Namenorbolethone
CAS Registry Number1235-15-0
SMILES
[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
InChI Identifier
InChI=1S/C21H32O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h13,16-19,23H,3-12H2,1-2H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChI KeyFTBJKONNNSKOLX-XUDSTZEESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0098 g/LALOGPS
logP4.02ALOGPS
logP4.31ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19.28ChemAxon
pKa (Strongest Basic)-0.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.72 m³·mol⁻¹ChemAxon
Polarizability38.16 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.95531661259
DarkChem[M-H]-172.14831661259
DeepCCS[M-2H]-211.84230932474
DeepCCS[M+Na]+186.24930932474
AllCCS[M+H]+182.132859911
AllCCS[M+H-H2O]+179.232859911
AllCCS[M+NH4]+184.732859911
AllCCS[M+Na]+185.532859911
AllCCS[M-H]-186.532859911
AllCCS[M+Na-2H]-186.932859911
AllCCS[M+HCOO]-187.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Norbolethone[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]3745.9Standard polar33892256
Norbolethone[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]2738.0Standard non polar33892256
Norbolethone[H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]2876.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norbolethone,1TMS,isomer #1CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC2929.8Semi standard non polar33892256
Norbolethone,1TMS,isomer #2CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC2803.4Semi standard non polar33892256
Norbolethone,2TMS,isomer #1CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC2855.5Semi standard non polar33892256
Norbolethone,2TMS,isomer #1CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC2901.9Standard non polar33892256
Norbolethone,2TMS,isomer #1CC[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3179.9Standard polar33892256
Norbolethone,1TBDMS,isomer #1CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC3175.7Semi standard non polar33892256
Norbolethone,1TBDMS,isomer #2CC[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3068.3Semi standard non polar33892256
Norbolethone,2TBDMS,isomer #1CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3381.8Semi standard non polar33892256
Norbolethone,2TBDMS,isomer #1CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3367.2Standard non polar33892256
Norbolethone,2TBDMS,isomer #1CC[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@@H]4[C@H]3CC[C@@]21CC3365.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norbolethone GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1291000000-d413aaf2b4edf20003602017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norbolethone GC-MS (1 TMS) - 70eV, Positivesplash10-0c00-1119000000-352ad6792758ae9d94d72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norbolethone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 10V, Positive-QTOFsplash10-00kb-0095000000-cda25eaf9c10361b92222017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 20V, Positive-QTOFsplash10-0002-0191000000-7aa90a3e0c0842920d992017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 40V, Positive-QTOFsplash10-05di-1690000000-4a138059002b023720e82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 10V, Negative-QTOFsplash10-014i-0029000000-98b78b3afa508c81ab7b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 20V, Negative-QTOFsplash10-014i-0069000000-9be5f2e135e6a2d1b47d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 40V, Negative-QTOFsplash10-052s-0090000000-810ee3872d7cdf37d1e02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 10V, Negative-QTOFsplash10-014i-0009000000-be6e06313d0abca8e6642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 20V, Negative-QTOFsplash10-014i-0019000000-eb65f94e6914722e1b9c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 40V, Negative-QTOFsplash10-014i-0092000000-3816ecdb5ba24754d3962021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 10V, Positive-QTOFsplash10-00kb-0096000000-12094c8bb5dfd35602b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 20V, Positive-QTOFsplash10-01ba-0791000000-6a375c28af2bcbf46d2b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbolethone 40V, Positive-QTOFsplash10-0691-1900000000-118c6246477fc37b89c42021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023805
KNApSAcK IDNot Available
Chemspider ID59638
KEGG Compound IDD05204
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorboletone
METLIN IDNot Available
PubChem Compound66255
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Catlin DH, Ahrens BD, Kucherova Y: Detection of norbolethone, an anabolic steroid never marketed, in athletes' urine. Rapid Commun Mass Spectrom. 2002;16(13):1273-5. [PubMed:12112254 ]