Compound: BOLANDIOL
SMILES: O[C@@H]1C=C2[C@@H]([C@@H]3[C@H]([C@H]4[C@]([C@@H](O)CC4)(C)CC3)CC2)CC1
InChIKey: CMXKUJNZWYTFJN-XFUVECHXSA-N
Synonyms: BOLANDIOL, 19793-20-5, 19-Nor-4-androstenediol, 4-norendiol, bolandiolum, 19-nortestosterone-3beta,17beta-diol, 3beta,17beta-dihydroxyestr-4-ene, 49SD6G16U5, DTXSID9041027, CHEBI:145661, RefChem:120883, DTXCID7021027, (1S,2R,5S,10R,11S,14S,15S)-15-methyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadec-6-ene-5,14-diol, Bolandiol [INN], UNII-49SD6G16U5, estr-4-ene-3beta,17beta-diol, (3S,8R,9S,10R,13S,14S,17S)-13-methyl-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol, 3.beta.,17.beta.-dihydroxyestr-4-ene, Bolandiol (1.0mg/ml in Acetonitrile), (3beta,17beta)-Estr-4-ene-3,17-diol; Estr-4-ene-3beta,17beta-diol; 19-Nor-4-androstene-3beta,17beta-diol; Norandrodiol Select 300; delta4-Estrene-3beta,17beta-diol, 3beta-dihydronandrolone, 19-norandrosta-4-ene-3beta,17beta-diol, BOLANDIOL [MI], 3.beta.-dihydronandrolone, BOLANDIOL [MART.], 4-estren-3beta,17beta-diol, Estr-4-ene-3,17-diol, (3.beta.,17.beta.)-, SCHEMBL547771, CHEMBL307500, CMXKUJNZWYTFJN-XFUVECHXSA-N, DB01554, FN66092, MSK011090-100M, Bolandiol Solution in Methanol, 100ug/mL, NS00071783, Q4938924, (3.BETA.,17.BETA.)-ESTR-4-ENE-3,17-DIOL, 19-NOR-4-ANDROSTENE-3.BETA.0,17.BETA.-DIOL, (1S,3aS,3bR,7S,9aR,9bS,11aS)-11a-methyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthrene-1,7-diol
Theoretical properties:
molecular_formula: C18H28O2
molecular_weight: 276.4 g/mol
exact_mass: 276.208930132 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 20
topological_polar_surface_area: 40.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Bolandiol is a 3beta-hydroxy steroid that is estr-4-ene substituted by a beta-hydroxy group at positions 3 and 17. It is a synthetic anabolic steroid that is used as a dietary supplement by athletes to enhance performance. It has a role as a nutraceutical and a prohormone. It is a diol, a 17beta-hydroxy steroid, a 3beta-hydroxy steroid and an anabolic androgenic steroid. It derives from a hydride of an estrane.
chebi: A 3β-hydroxy steroid that is estr-4-ene substituted by a β-hydroxy group at positions 3 and 17. It is a synthetic anabolic steroid that is used as a dietary supplement by athletes to enhance performance.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Bolandiol (INN, also known as 19-nor-4-androstenediol, estr-4-ene-3β,17β-diol, or 3β-dihydronandrolone) is an anabolic-androgenic steroid (AAS) that was never marketed. However, a dipropionate ester derivative, bolandiol dipropionate, has been marketed. Bolandiol and its dipropionate ester are unique among AASs in that they reportedly also possesses estrogenic and progestogenic activity.
Bolandiol is on the World Anti-Doping Agency's list of prohibited substances, and is therefore banned from use in most major sports.  It is a potential metabolic precursor (via 3β-HSD) to nandrolone or a derivative of nandrolone (via 3β-hydroxy-steroid:NADP+ 3-oxidoreductase). However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance.