Compound: androsterone
SMILES: O=C1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@H](C[C@H](O)CC4)CC3)C)CC2)CC1)C
InChIKey: QGXBDMJGAMFCBF-HLUDHZFRSA-N
Synonyms: androsterone, 53-41-8, Androkinine, Androtine, 3alpha-Hydroxy-5alpha-androstan-17-one, 5alpha-Androsterone, 3-Epihydroxyetioallocholan-17-one, 3alpha-Hydroxyetioallocholan-17-one, 5alpha-Androstane-3alpha-ol-17-one, 3alpha-Hydroxy-17-androstanone, 3-alpha-Hydroxy-5-alpha-androstan-17-one, Androstan-17-one, 3-hydroxy-, (3alpha,5alpha)-, (3alpha,5alpha)-3-hydroxyandrostan-17-one, (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one, C24W7J5D5R, DTXSID3036525, CHEBI:16032, NSC-9898, DTXCID1016525, (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta(a)phenanthren-17-one, RefChem:112651, 5 alpha Androstan 3 alpha ol 17 one, 5 alpha-Androstan-3 alpha-ol-17-one, 3 alpha Hydroxy 5 alpha Androstan 17 One, (1S,2S,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo(8.7.0.02,7.011,15)heptadecan-14-one, 200-173-4, Atromide ICI, cis-Androsterone, Androstanon-3-alpha-ol-17-one, 3-alpha-Hydroxy-17-androstanone, 3-alpha-Hydroxyetioallocholan-17-one, 5-alpha-Androstan-3-alpha-ol-17-one, Androstan-17-one, 3-hydroxy-, (3a,5a)-, 5alpha-Androstan-17-one, 3alpha-hydroxy-, 5alpha-Androstan-3alpha-ol-17-one, 5.alpha.-Androsterone, Androstan-17-one, 3-hydroxy-, (3-alpha,5-alpha)-, 3.alpha.-Hydroxy-17-androstanone, U 6036, CHEMBL87285, MLS000069394, 5-alpha-Androstan-17-one, 3-alpha-hydroxy-, NSC 9898, 3.alpha.-Hydroxyetioallocholan-17-one, SMR000058571, 5.alpha.-Androstane-3.alpha.-ol-17-one, 5.alpha.-Androstan-17-one, 3.alpha.-hydroxy-, trans-Androsterone, Caswell No. 051G, Androsterone, epi-, MFCD00003618, Androsterone, trans-, Androsterone (1mg/ml in Acetonitrile), Androstan-17-one, 3-hydroxy-, (3.alpha.,5.alpha.)-, Esterase basic kit, (1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one, 3-Hydroxyandrostan-17-one, EINECS 200-173-4, EPA Pesticide Chemical Code 126501, BRN 2217626, UNII-C24W7J5D5R, 3-.beta.Hydroxyandrostan-17-one, Androsterolone, (3?,5?)-3-Hydroxyandrostan-17-one, CAS-53-41-8, 5.alpha.-Androstan-3.beta.-ol-17-one, (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-one, AOI, Prestwick_689, 5-alpha-Androsterone, 1x8j, Opera_ID_584, Prestwick0_000411, Prestwick1_000411, Prestwick2_000411, Prestwick3_000411, ANDROSTERONE [MI], bmse000543, Epitope ID:174330, UPCMLD-DP124, 5-androstan-3-ol-17-one, BSPBio_000362, 4-08-00-00642 (Beilstein Handbook Reference), MLS000563085, MLS001146886, MLS002153256, SCHEMBL269981, SPBio_002301, rocuronium bromide impurity 50, BPBio1_000400, orb2281184, UPCMLD-DP124:001, BDBM17639, MSK8508, NSC9898, HMS1569C04, HMS2096C04, HMS2230I18, HMS3713C04, HY-N0933, 3?-HYDROXY-17-ANDROSTANONE, Tox21_303701, LMST02020001, MSK8508-100A, s6352, 5-alpha-Androstane-3alpha-ol-17-one, AKOS015894886, MSK8508-1000A, CCG-220411, FH17918, GS-3614, 3alpha-hydroxy-5alpha-androstane-17-one, NCGC00161664-01, NCGC00161664-02, NCGC00357021-01, (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-Dimethylhexadecahydro-17H-cyclopenta[a]phenanthren-17-one, 3-alpha-hydroxy-5alpha-Androstan-17-one, AC-16145, 3-alpha-Hydroxy-5-alpha-androstane-17-one, A0646, CS-0014230, NS00010906, Androstan-17-one, 3alpha-hydroxy-, 5alpha-, C00523, 3-hydroxy-(3-alpha,5-alpha)-Androstan-17-one, Androsterone Solution in Acetonitrile, 100ug/mL, Androsterone, VETRANAL(TM), analytical standard, Androsterone Solution in Acetonitrile, 1000ug/mL, Q422469, SR-01000759187, SR-01000759187-3, 3.ALPHA.-HYDROXY-5.ALPHA.-ANDROSTAN-17-ONE, BRD-K12329651-001-18-8, (3.ALPHA.,5.ALPHA.)-3-HYDROXYANDROSTAN-17-ONE, 086DA2D0-D9AE-4593-9E08-991AF2BF2A47, (3alpha,5beta,8alpha,10alpha,13alpha,14beta)-3-hydroxyandrostan-17-one, (1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0?,?.0??,??]heptadecan-14-one, (3R,5S,8R,10S,13S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
Theoretical properties:
molecular_formula: C19H30O2
molecular_weight: 290.4 g/mol
exact_mass: 290.224580195 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 21
topological_polar_surface_area: 37.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 185 °C
solubility: 0.012 mg/mL at 23 °C
Descriptions:
pubchem: Androsterone is an androstanoid that is 5alpha-androstane having a hydroxy substituent at the 3alpha-position and an oxo group at the 17-position. It is a metabolite of dehydroepiandrosterone. It has a role as a pheromone, an anticonvulsant, an androgen, a mouse metabolite, a human metabolite, a human urinary metabolite and a human blood serum metabolite. It is a C19-steroid, a 17-oxo steroid, a 3alpha-hydroxy steroid and an androstanoid. It derives from a hydride of a 5alpha-androstane.
chebi: An androstanoid that is 5α-androstane having a hydroxy substituent at the 3α-position and an oxo group at the 17-position. It is a metabolite of dehydroepiandrosterone .
chembl: ANDROSTERONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone, neurosteroid, and putative pheromone. It is a weak androgen with a potency that is approximately 1/7 that of testosterone. Androsterone is a metabolite of testosterone and dihydrotestosterone (DHT). In addition, it can be converted back into DHT via 3α-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase, bypassing conventional intermediates such as androstanedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right.
Androsterone is also known to be an inhibitory androstane neurosteroid, acting as a positive allosteric modulator of the GABAA receptor, and possesses anticonvulsant effects. The unnatural enantiomer of androsterone is more potent as a positive allosteric modulator of GABAA receptors and as an anticonvulsant than the natural form. Androsterone's 3β-isomer is epiandrosterone, and its 5β-epimer is etiocholanolone. The 3β,5β-isomer is epietiocholanolone.