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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-08-13 22:41:35 UTC
Update Date2020-02-26 21:25:10 UTC
HMDB IDHMDB0004631
Secondary Accession Numbers
  • HMDB04631
Metabolite Identification
Common NameFormebolone
DescriptionFormebolone is a synthetic anabolic steroid. It is suspected of misuse in sports and therefore tested for in regular screening of athletes. The desire to artificially enhance physical performance in order to increase the chances to win in sports competition is supposedly as old as mankind itself. Already during the ancient Olympic Games, in approximately 200 B.C., athletes used concoctions of mushrooms and plant seeds, as well as special diets including bovine and canine testicles, as reported by Philostratos and Galen. The attempt to improve the power and strength of racing animals also has a long history, as it has been reported that the ancient Romans fed their horses so-called 'Hydromel', a mixture of honey and water, in order to increase endurance. The manipulation of the capacities of an athlete or animal has been referred to as doping since 1889, when this term, originating from a dialect spoken in the south-eastern region of Africa, was included in a British dictionary. With the athlete Linton, the first authentic doping-related death occurred in 1886 during a cycle race (Paris-Bordeaux), caused by an overdose of caffeine. (For a more complete review on doping see PMID: 15808003 ).
Structure
Data?1582752310
Synonyms
ValueSource
(11a,17b)-11,17-Dihydroxy-17-methyl-3-oxo-androsta-1,4-diene-2-carboxaldehydeHMDB
11a,17b-Dihydroxy-17-methyl-3-oxo-androsta-1,4-diene-2-carboxaldehydeHMDB
11a,17b-Dihydroxy-17-methyl-3-oxoandrosta-1,4-diene-2-carboxaldehydeHMDB
2-Formyl-11a-hydroxy-D1-methyltestosteroneHMDB
2-Formyl-17a-methylandrosta-1,4-dien-11a,17b-diol-3-oneHMDB
2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-dihydroxy-3-oneHMDB
2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-diol-3-oneHMDB
EsicleneHMDB
FormyldienoloneHMDB
2-Formyl-17 alpha-methylandrosta-1,4-diene-11 alpha,17 beta-diol-3-oneHMDB
Formyldienolone, (11 beta,17beta)-isomerHMDB
FormildienoloneHMDB
FormeboloneMeSH
Chemical FormulaC21H28O4
Average Molecular Weight344.4446
Monoisotopic Molecular Weight344.198759384
IUPAC Name(1S,2R,10S,11S,14S,15S,17R)-14,17-dihydroxy-2,14,15-trimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-4-carbaldehyde
Traditional Nameformebolone
CAS Registry Number2454-11-7
SMILES
[H][C@@]12CC[C@](C)(O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C(C=O)=C[C@]12C
InChI Identifier
InChI=1S/C21H28O4/c1-19-9-12(11-22)16(23)8-13(19)4-5-14-15-6-7-21(3,25)20(15,2)10-17(24)18(14)19/h8-9,11,14-15,17-18,24-25H,4-7,10H2,1-3H3/t14-,15-,17+,18+,19-,20-,21-/m0/s1
InChI KeyAMVODTGMYSRMNP-GNIMZFFESA-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-1,4-steroid
  • 3-oxosteroid
  • Hydroxysteroid
  • Oxosteroid
  • 11-alpha-hydroxysteroid
  • 11-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Secondary alcohol
  • Ketone
  • Cyclic ketone
  • Aldehyde
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point209 - 212 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.06 g/LALOGPS
logP2.59ALOGPS
logP1.76ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.39ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity96.9 m³·mol⁻¹ChemAxon
Polarizability38.13 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00or-1549000000-42102185d1dded40eceaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3506900000-e9c4f9b646ae0846ac95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-83d05b9ec6d4114e8a0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0239000000-e2958d7b5f276c7c8f72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0rkd-2294000000-a7c54e1065ffa26a8568Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-be5664450200906ba6e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0009000000-51507deb2305cd3590afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ta-1196000000-a3d80644f38949e4fd48Spectrum
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 IDDB01569
Phenol Explorer Compound IDNot Available
FooDB IDFDB023388
KNApSAcK IDNot Available
Chemspider ID16234
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFormebolone
METLIN IDNot Available
PubChem Compound17150
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceCanonica, Luigi; Jommi, Giancarlo; Pelizzoni, Francesca; Scolastico, Carlo. 1,11-Oxido steroids. I. 1a,11a-Oxidoandrostanes. Gazzetta Chimica Italiana (1965), 95(3), 138-50.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thevis M, Schanzer W: Examples of doping control analysis by liquid chromatography-tandem mass spectrometry: ephedrines, beta-receptor blocking agents, diuretics, sympathomimetics, and cross-linked hemoglobins. J Chromatogr Sci. 2005 Jan;43(1):22-31. [PubMed:15808003 ]