Compound: Epitestosterone
SMILES: O=C1C=C2[C@]([C@@H]3[C@H]([C@H]4[C@]([C@H](O)CC4)(C)CC3)CC2)(C)CC1
InChIKey: MUMGGOZAMZWBJJ-KZYORJDKSA-N
Synonyms: Epitestosterone, 481-30-1, Isotestosterone, cis-Testosterone, 17-Epitestosterone, 17alpha-Hydroxyandrost-4-en-3-one, 17-alpha-Testosterone, 17alpha-Testosterone, 17alpha-cis-Testosterone, 17-alpha-Hydroxyandrost-4-en-3-one, DTXSID8022329, (17-alpha)-17-Hydroxyandrost-4-en-3-one, NSC-26499, (8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one, Androst-4-en-3-one, 17-hydroxy-, (17alpha)-, DTXCID002329, 48L726977Z, CHEBI:42534, 17 alpha Testosterone, (8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta(a)phenanthren-3-one, RefChem:137304, epi-Testosterone, 17-epi-Testosterone, NSC 26499, 17.alpha.-Testosterone, Testosterone, cis-, alpha epitestosterone, 17.alpha.-Hydroxyandrost-4-en-3-one, (17alpha)-17-hydroxyandrost-4-en-3-one, (10alpha,13alpha,14beta,17alpha)-17-Hydroxyandrost-4-En-3-One, Androst-4-en-3-one, 17.alpha.-hydroxy-, Androst-4-en-3-one, 17-hydroxy-, (17.alpha.)-, 17alpha-Hydroxyandrost-4-en-3-one (Epitestosterone), Testosterone EP Impurity C, BRN 1915396, 4-Androsten-17.alpha.-ol-3-one, UNII-48L726977Z, NCGC00091018-01, MFCD00067129, 17a-cis-Testosterone, Androst-4-en-3-one, 17alpha-hydroxy-, 17-Hydroxyandrost-4-en-3-one, (17.alpha.)-, ANDROST-4-EN-3-ONE, 17-alpha-HYDROXY-, EPITESTOSTERONE [MI], Androst-4-en-3-one, 17-hydroxy-, (17-alpha)-, BIDD:ER0485, SCHEMBL334193, CHEMBL196228, 17.ALPHA.-CIS-TESTOSTERONE, NSC26499, Tox21_111058, BDBM50410492, LMST02020051, MSK2266-100A, MSK2266-1000A, DB07768, FE22743, Androst-4-en-3-one, (17.alpha.)-, SMP2_000253, NCGC00091018-02, CAS-481-30-1, Epitestosterone 1.0 mg/ml in Acetonitrile, 4-ANDROSTENE-17.ALPHA.-OL-3-ONE, ANDROST-4-EN-17.ALPHA.-OL-3-ONE, DB-222500, NS00008414, TESTOSTERONE IMPURITY C [EP IMPURITY], Q416852, Epitestosterone Solution in Acetonitrile, 1000ug/mL, Epitestosterone Solution in Acetonitrile, 100ug/mL, BRD-K25836724-001-01-6, (8R,10R,13S,17R)-17-Hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one, (8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
Theoretical properties:
molecular_formula: C19H28O2
molecular_weight: 288.4 g/mol
exact_mass: 288.208930132 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: Epitestosterone is an androstanoid that is the C-17 epimer of testosterone. It has a role as an androgen antagonist and a human metabolite. It is a 17alpha-hydroxy steroid, a 3-oxo-Delta(4) steroid and an androstanoid.
chebi: An androstanoid that is the <em>C</em>-17 epimer of testosterone.
chembl: EPITESTOSTERONE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Epitestosterone, or isotestosterone, also known as 17α-testosterone or as androst-4-en-17α-ol-3-one, is an endogenous steroid and an epimer of the androgen sex hormone testosterone. It is a weak competitive antagonist of the androgen receptor (AR) and a potent 5α-reductase inhibitor.
Structurally, epitestosterone differs from testosterone only in the configuration at the hydroxy-bearing carbon, C17. Epitestosterone is believed to form in a similar way to testosterone; a 1993 study found that around 50% of epitestosterone production in human males can be ascribed to the testis, although the exact pathway of its formation is still the subject of research. It has been shown to accumulate in mammary cyst fluid and in the prostate. Epitestosterone levels are typically highest in young males; however, by adulthood, most healthy males exhibit a testosterone to epitestosterone ratio (T/E ratio) of about 1:1.