1.02011-09-21 00:29:11 UTC2015-07-21 06:57:41 UTCFDB023388FormeboloneFormebolone 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) [HMDB](11a,17b)-11,17-dihydroxy-17-methyl-3-oxo-Androsta-1,4-diene-2-carboxaldehyde11a,17b-dihydroxy-17-methyl-3-oxo-Androsta-1,4-diene-2-carboxaldehyde11a,17b-Dihydroxy-17-methyl-3-oxoandrosta-1,4-diene-2-carboxaldehyde2-Formyl-11a-hydroxy-D1-methyltestosterone2-Formyl-17a-methylandrosta-1,4-dien-11a,17b-diol-3-one2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-dihydroxy-3-one2-Formyl-17a-methylandrosta-1,4-diene-11a,17b-diol-3-oneEsicleneFormyldienoloneC21H28O4344.4446344.198759384(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-carbaldehydeformebolone2454-11-7[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@]12CInChI=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/s1AMVODTGMYSRMNP-GNIMZFFESA-N 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.Androgens and derivativesOrganic compoundsLipids and lipid-like moleculesSteroids and steroid derivativesAndrostane steroidsAliphatic homopolycyclic compounds11-alpha-hydroxysteroids17-hydroxysteroids3-oxo delta-1,4-steroidsAldehydesCyclic alcohols and derivativesCyclic ketonesDelta-1,4-steroidsHydrocarbon derivativesOrganic oxidesSecondary alcoholsTertiary alcohols11-alpha-hydroxysteroid11-hydroxysteroid17-hydroxysteroid3-oxo-delta-1,4-steroid3-oxosteroidAlcoholAldehydeAliphatic homopolycyclic compoundAndrogen-skeletonCarbonyl groupCyclic alcoholCyclic ketoneDelta-1,4-steroidHydrocarbon derivativeHydroxysteroidKetoneOrganic oxideOrganic oxygen compoundOrganooxygen compoundOxosteroidSecondary alcoholTertiary alcoholSolidlogp2.59logs-3.76solubility6.05e-02 g/llogp1.76pka_strongest_acidic14.39pka_strongest_basic-2.9iupac(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-carbaldehydeaverage_mass344.4446mono_mass344.198759384smiles[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@]12CformulaC21H28O4inchiInChI=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/s1inchikeyAMVODTGMYSRMNP-GNIMZFFESA-Npolar_surface_area74.6refractivity96.9polarizability38.13rotatable_bond_count1acceptor_count4donor_count2physiological_charge0formal_charge0Specdb::CMs16298Specdb::CMs38775Specdb::CMs172152Specdb::MsMs255882Specdb::MsMs255883Specdb::MsMs255884Specdb::MsMs275823Specdb::MsMs275824Specdb::MsMs275825Specdb::MsMs2467193Specdb::MsMs2467194Specdb::MsMs2467195Specdb::MsMs2498540Specdb::MsMs2498541Specdb::MsMs2498542HMDB04631#<Reference:0x00005556749d0998>