Compound: ADRENOSTERONE
SMILES: O=C1C=C2[C@]([C@H]3C(=O)C[C@@]4(C(=O)CC[C@H]4[C@@H]3CC2)C)(C)CC1
InChIKey: RZRPTBIGEANTGU-IRIMSJTPSA-N
Synonyms: ADRENOSTERONE, 382-45-6, Androst-4-ene-3,11,17-trione, Andrenosterone, Reichstein's substance G, 11-Ketoandrostenedione, 11-Oxy-4-androstenedione, 11-Keto-androstenedione, 11-OXO, NSC 12166, AE4E9102GY, DTXSID801019311, NSC-12166, CHEBI:2495, (1S,2R,10S,11S,15S)-2,15-dimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadec-6-ene-5,14,17-trione, (1S,2R,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14,17-trione, RefChem:915191, DTXCID901477289, 206-843-2, 4-Androstene-3,11,17-trione, 11-Oxoandrostenedione, C19H24O3, MFCD00003606, MLS000028712, MLS001146874, (8S,9S,10R,13S,14S)-10,13-dimethyl-1,2,6,7,8,9,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,11,17-trione, 11-oxoandrost-4-ene-3,17-dione, (+)-Adrenosterone, SMR000059216, (8S,9S,10R,13S,14S)-10,13-dimethyl-6,7,8,9,10,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,11,17(2H)-trione, 82043-34-3, Adrenosterone (1.0mg/ml in Acetonitrile), adrenoterone, UNII-AE4E9102GY, Adrenosteron, EINECS 206-843-2, Adrenosterone, 98%, (+/-)-Adrenosterone, Opera_ID_1090, Prestwick0_000899, Prestwick1_000899, Prestwick2_000899, Prestwick3_000899, Prednisolone Impurity 78, ADRENOSTERONE [MI], bmse000522, BSPBio_000718, Androst-4-ene-3,17-trione, SCHEMBL329751, SPBio_002927, BPBio1_000790, CHEMBL485683, 11-oxo4-androstene-3,17-dione, DTXSID301020915, HMS1570D20, HMS2097D20, HMS2231O24, HMS3714D20, NSC12166, 11-Oxo-4-androstene-3,17-dione, 11-Keto-4-androstene-3,17-dione, MSK157206, s4773, AKOS015919184, CCG-220899, CS-1756, FA17228, MSK157206-100A, Adrenosterone (1 mg/ml in Acetonitrile), NCGC00179466-01, NCGC00179466-06, 911474-75-4, AS-56448, HY-17462, A1397, AB00513953, NS00042221, C05285, Adrenosterone Solution in Acetonitrile, 100ug/mL, SR-01000721947, Q-200603, Q4684756, SR-01000721947-3, BRD-K17368287-001-03-5, BRD-K17368287-001-18-3, 793B9701-82B7-46F0-BDC7-04C33B82723A, (8S,10R,13S)-10,13-Dimethyl-1,2,6,7,8,9,10,12,13,14,15,16-dodecahydro-cyclopenta[a]phenanthrene-3,11,17-trione, (8S,9S,10R,13S,14S)-10,13-dimethyl-7,8,10,12,13,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,11,17(2H,6H,9H)-trione, 2,5,8(6H)-Chrysenetrione, 7-((acetyloxy)methyl)-3,4,4a,4b,6a,7,9,10,10a,10b,11,12-dodecahydro-7-hydroxy-4a,6a-dimethyl-, (4aR,4bS,6aS,7R,10aS,10bS)-
Theoretical properties:
molecular_formula: C19H24O3
molecular_weight: 300.4 g/mol
exact_mass: 300.17254462 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 22
topological_polar_surface_area: 51.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Adrenosterone is a 3-oxo 4-steroid that is androst-4-ene carrying three oxo-substituents at positions 3, 11 and 17. It has a role as an EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor, an androgen, a marine metabolite and a human urinary metabolite. It is a 17-oxo steroid, an 11-oxo steroid, a 3-oxo-Delta(4) steroid and an androstanoid. It derives from a hydride of an androstane.
chebi: A 3-oxo Δ<small><sup>4</small></sup>-steroid that is androst-4-ene carrying three oxo-substituents at positions 3, 11 and 17.
chembl: ADRENOTERONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Adrenosterone, also known as Reichstein's substance G , as well as 11-ketoandrostenedione (11-KA4), 11-oxoandrostenedione (11-OXO), and androst-4-ene-3,11,17-trione, is a steroid hormone with an extremely weak androgenic effect, and an intermediate/prohormone of 11-ketotestosterone. It was first isolated in 1936 from the adrenal cortex by Tadeus Reichstein at the Pharmaceutical Institute in the University of Basel. Originally, adrenosterone was called Reichstein's substance G. Adrenosterone occurs in trace amounts in humans as well as most mammals and in larger amounts in fish, where it is a precursor to the primary androgen, 11-ketotestosterone.
Adrenosterone is sold as a dietary supplement since 2007 as a fat loss and muscle gaining supplement.  It is thought to be a competitive selective 11βHSD1 inhibitor, which is responsible for activation of cortisol from cortisone. Thus preventing muscle breakdown, and contributing to a majority of its effects.
Adrenosterone is used as an intermediate in the synthesis of fluoxymesterone and in the RTI synthesis of dimethandrolone.