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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:26 UTC
Update Date2022-03-07 02:57:14 UTC
HMDB IDHMDB0041928
Secondary Accession Numbers
  • HMDB41928
Metabolite Identification
Common NameMethenolone
DescriptionMetenolone (or methenolone) is a long-acting anabolic steroid with weak androgenic (testosterone or androsterone-like) properties. It is a naturally occurring drug, found within the adrenal glands of pregnant domesticated felines, and is supplied as the acetate ester for oral administration and as the enanthate ester for intramuscular injection. Adult doses for the treatment of aplastic anemia are usually in a range of 1-3 mg/kg per day.
Structure
Data?1563863715
Synonyms
ValueSource
1-Methyl-3-oxoandrost-1-en-17-yl heptanoate (acd/name 4.0)HMDB
17alpha-Androst-1-en-3-one heptanoateHMDB
Metenolone enanthateHMDB
Methenolone enanthateHMDB
MetenoloneHMDB
Chemical FormulaC20H30O2
Average Molecular Weight302.451
Monoisotopic Molecular Weight302.224580204
IUPAC Name(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-en-5-one
Traditional Namemethenolone
CAS Registry Number303-42-4
SMILES
[H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)C=C(C)[C@]4(C)[C@@]3([H])CC[C@]12C
InChI Identifier
InChI=1S/C20H30O2/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/h10,13,15-18,22H,4-9,11H2,1-3H3/t13-,15-,16-,17-,18-,19-,20-/m0/s1
InChI KeyANJQEDFWRSLVBR-VHUDCFPWSA-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-1-steroid
  • 3-oxosteroid
  • 3-oxo-5-alpha-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-1-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility0.022 g/LALOGPS
logP3.45ALOGPS
logP3.65ChemAxon
logS-4.1ALOGPS
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
Refractivity88.98 m³·mol⁻¹ChemAxon
Polarizability35.87 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]+173.01331661259
DarkChem[M-H]-168.78531661259
DeepCCS[M-2H]-199.46930932474
DeepCCS[M+Na]+173.86330932474
AllCCS[M+H]+177.232859911
AllCCS[M+H-H2O]+174.232859911
AllCCS[M+NH4]+179.932859911
AllCCS[M+Na]+180.732859911
AllCCS[M-H]-182.032859911
AllCCS[M+Na-2H]-182.232859911
AllCCS[M+HCOO]-182.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methenolone[H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)C=C(C)[C@]4(C)[C@@]3([H])CC[C@]12C3508.9Standard polar33892256
Methenolone[H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)C=C(C)[C@]4(C)[C@@]3([H])CC[C@]12C2573.8Standard non polar33892256
Methenolone[H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)C=C(C)[C@]4(C)[C@@]3([H])CC[C@]12C2818.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methenolone,1TMS,isomer #1CC1=CC(=O)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C2797.9Semi standard non polar33892256
Methenolone,1TMS,isomer #2CC1=CC(O[Si](C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]12C2665.4Semi standard non polar33892256
Methenolone,2TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C2668.0Semi standard non polar33892256
Methenolone,2TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C2739.1Standard non polar33892256
Methenolone,1TBDMS,isomer #1CC1=CC(=O)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C3034.6Semi standard non polar33892256
Methenolone,1TBDMS,isomer #2CC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]12C2889.0Semi standard non polar33892256
Methenolone,2TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C3168.3Semi standard non polar33892256
Methenolone,2TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]12C3227.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methenolone GC-MS (Non-derivatized) - 70eV, Positivesplash10-05g0-0290000000-541020c4a6431e6bc3392017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methenolone GC-MS (1 TMS) - 70eV, Positivesplash10-0592-4679000000-ad3f038a6d92a19f85ec2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methenolone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methenolone 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 - Methenolone 10V, Positive-QTOFsplash10-0f79-0195000000-d6e2130e5a72f40b1c022017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methenolone 20V, Positive-QTOFsplash10-0f79-0291000000-85fd4db178ebbf6734082017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methenolone 40V, Positive-QTOFsplash10-00kf-3980000000-556772f5244b5f3b227d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methenolone 10V, Negative-QTOFsplash10-0udi-0029000000-8f46e29158af0935ec892017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methenolone 20V, Negative-QTOFsplash10-0udi-0059000000-b1f0a818e6208b0d6be52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methenolone 40V, Negative-QTOFsplash10-00kr-2090000000-f3d2a8fd173fd09f12a52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methenolone 10V, Negative-QTOFsplash10-0udi-0009000000-16d58525184e918518fa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methenolone 20V, Negative-QTOFsplash10-0udi-0009000000-16d58525184e918518fa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methenolone 40V, Negative-QTOFsplash10-0002-0091000000-ec361b8e770c43bc5e1f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methenolone 10V, Positive-QTOFsplash10-0udi-0029000000-0103931e500d13b3abb62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methenolone 20V, Positive-QTOFsplash10-0v09-0962000000-e64fe8d6bebe16a8ce892021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methenolone 40V, Positive-QTOFsplash10-0a4i-6900000000-24ab90a547dbc41bc2952021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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 IDDB13710
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2301378
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetenolone
METLIN IDNot Available
PubChem Compound3037705
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.