Formebolone (CHEM035689)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:59:29 UTC
Update Date2016-11-09 01:21:21 UTC
Accession NumberCHEM035689
Identification
Common NameFormebolone
ClassSmall Molecule
DescriptionFormebolone, a derivative of androstane, is an anabolic androgenic steroid. It is on the list of substances prohibited by the Word Anti-Doping Agency, and is regularly screened for in athletes.[A14416] It is also classified by the US Drug Enforcement Administration as Schedule III drug in the Controlled Substances Act. It has been used experimentally in the treatment of growth retardation, and has been noted to increase bone mass.[A14416] Additionally, it has been patented for use in development of novel transdermal delivery systems for enhanced drug delivery.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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, MeSH
FormyldienoloneHMDB, MeSH
2-Formyl-17 alpha-methylandrosta-1,4-diene-11 alpha,17 beta-diol-3-oneMeSH, HMDB
Formyldienolone, (11 beta,17beta)-isomerMeSH, HMDB
FormildienoloneMeSH, HMDB
FormeboloneMeSH
Chemical FormulaC21H28O4
Average Molecular Mass344.445 g/mol
Monoisotopic Mass344.199 g/mol
CAS Registry Number2454-11-7
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
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 IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-132e2debff844207d185Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0019000000-440aecd91bd6be86b2b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0293000000-688a79dea37f10a0d946Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0019000000-4d6ca44432cd0e2ca971Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000e-3954000000-ac54633877d9786e5126Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4890000000-b21d6e58b198bff27fdaSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01569
HMDB IDHMDB0004631
FooDB IDFDB023388
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFormebolone
Chemspider ID16234
ChEBI IDNot Available
PubChem Compound ID17150
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Canonica, Luigi; Jommi, Giancarlo; Pelizzoni, Francesca; Scolastico, Carlo. 1,11-Oxido steroids. I. 1a,11a-Oxidoandrostanes. Gazzetta Chimica Italiana (1965), 95(3), 138-50.
2. Canonica, Luigi; Jommi, Giancarlo; Pelizzoni, Francesca; Scolastico, Carlo. 1,11-Oxido steroids. I. 1a,11a-Oxidoandrostanes. Gazzetta Chimica Italiana (1965), 95(3), 138-50.
3. 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.