Compound: EPIANDROSTERONE
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-LUJOEAJASA-N
Synonyms: EPIANDROSTERONE, 481-29-8, Isoandrosterone, iso-Androsterone, 3Beta-hydroxy-5alpha-androstan-17-one, d-Epiandrosterone, 3beta-Hydroxyetioallocholan-17-one, 3beta-Hydroxy-androstan-17-one, 8TR252Z538, CHEBI:541975, DTXSID20289698, NSC-93996, (3S,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, (3S,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:590907, DTXCID601030608, 207-563-3, trans-Androsterone, Androstan-17-one, 3-hydroxy-, (3b,5a)-, 5alpha-Androstan-3beta-ol-17-one, (3beta,5alpha)-3-hydroxyandrostan-17-one, MLS001304190, CHEMBL272195, Androsterone, epi-, NSC 93996, ST072176, epi-andosterone, Androsterone, trans-, (1S,2S,5S,7S,11S,15S,10R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0<2,7>.0<11, 15>]heptadecan-14-one, Epiandrosterone (1mg/mL in Acetonitrile), SMR000718744, 3.beta.-Hydroxy-5.alpha.-androstan-17-one, Androsterone, (3beta)-, Epiandrosterone?, MFCD00064134, UNII-8TR252Z538, 3?-Androsterone, (3?,5?)-3-Hydroxyandrostan-17-one, AOX, Prestwick_699, EINECS 207-563-3, 3|A-androsterone;EpiA, 3-beta-Hydroxy-5-alpha-androstan-17-one, Prestwick0_000440, Prestwick1_000440, Prestwick2_000440, Prestwick3_000440, EC 207-563-3, EPIANDROSTERONE [MI], BSPBio_000460, MLS000563092, MLS001333976, MLS001333977, MLS002153812, orb341615, SCHEMBL295167, SPBio_002399, BPBio1_000506, Rocuronium Bromide Impurity 30, MSK2201, HMS1569G22, HMS2096G22, HMS2235I04, HMS3713G22, HMS3884L18, Epiandrosterone (3|A-androsterone), HY-I0352, BBL030012, BDBM50236240, LMST02020023, MSK2201-100A, s2832, SBB012505, STK801866, AKOS001582886, CCG-220440, CS-5183, FE22714, NCGC00142619-02, NCGC00142619-04, AC-16141, AS-13045, 5alpha-Androstan-17-one, 3beta-hydroxy-, (3beta, 5alpha)-androstan-3-ol- 17-one, E0374, NS00067046, NS00124666, Epiandrosterone 100 microg/mL in Acetonitrile, C07635, 3-Androsterone;trans-Androsterone;iso-Androsterone, SR-01000837513, Epiandrosterone Solution in Acetonitrile, 100ug/mL, Q5382412, SR-01000837513-2, (3S,5S,8R,10S,13S)-3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one, (3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-17(2H)-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:
Descriptions:
pubchem: Epiandrosterone is a 3beta-hydroxy steroid that is (5alpha)-androstane substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It has a role as an androgen and a human metabolite. It is a 17-oxo steroid, a 3beta-hydroxy steroid and an androstanoid. It is functionally related to a 5alpha-androstane.
chebi: A 3β-hydroxy steroid that is (5α)-androstane substituted by a β-hydroxy group at position 3 and an oxo group at position 17.
chembl: EPIANDROSTERONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Epiandrosterone, or isoandrosterone, also known as 3β-androsterone, 3β-hydroxy-5α-androstan-17-one, or 5α-androstan-3β-ol-17-one, is a steroid hormone with weak androgenic activity. It is a metabolite of testosterone and dihydrotestosterone (DHT). It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline androsterone (most likely mixed isomers), which was sufficient to find that the chemical formula was very similar to estrone.
Epiandrosterone has been shown to naturally occur in most mammals including pigs.
Epiandrosterone is naturally produced by the enzyme 5α-reductase from the adrenal hormone DHEA.  Epiandrosterone can also be produced from the natural steroids androstanediol via 17β-hydroxysteroid dehydrogenase or from androstanedione via 3β-hydroxysteroid dehydrogenase.