Compound: 4-Androstenediol
SMILES: O[C@@H]1C=C2[C@]([C@@H]3[C@H]([C@H]4[C@]([C@@H](O)CC4)(C)CC3)CC2)(C)CC1
InChIKey: BTTWKVFKBPAFDK-LOVVWNRFSA-N
Synonyms: 4-Androstenediol, 1156-92-9, Androst-4-ene-3beta,17beta-diol, UNII-G10EHA9I0D, G10EHA9I0D, Androst-4-ene-3.beta.,17.beta.-diol, 4-ANDENDIOL, 3beta,17beta-Dihydroxy-4-androstene, delta4-Androstene-3beta,17beta-diol, NSC 12458, NSC-12458, (3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol, 4-Androstene-3b,17b-diol, androst-4-en-3b,17b-diol, D4-Androstene-3b,17b-diol, Androst-4-ene-3b,17b-diol, 3b,17b-Dihydroxy-4-androstene, 4-Androsten-3beta,17beta-diol, DTXSID5036505, ANDROST-4-ENE-1,1 DIOL, (3b,17b)-Androst-4-ene-3,17-diol, 3.beta.,17.beta.-Dihydroxy-4-androstene, TESTOSTERONE IMPURITY D [EP IMPURITY], .DELTA.4-Androstene-3.beta.,17.beta.-diol, 4-ANDROSTENE-3.BETA.O,17.BETA.-DIOL, Androst-4-ene-3,17-diol, (3beta,17beta)-, TESTOSTERONE IMPURITY D (EP IMPURITY), Androst-4-ene-3,17-diol, (3.beta.,17.beta.)-, (3S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta(a)phenanthrene-3,17-diol, Androst-4-ene-3beta,17beta-diol (8CI), RefChem:97891, DTXCID3016505, Androst-4-ene-3I2,17I2-diol, 4-ANDROSTENE-3BETAO,17BETA-DIOL, (3beta,17beta)-Androst-4-ene-3,17-diol, Androst-4-ene-3,17-diol, (3beta,17beta)-(9CI), BTTWKVFKBPAFDK-WJWLXVOASA-N, Testosterone EP Impurity D, CHEMBL195836, Androst-4-ene-3,17-diol, 4-androstene-3beta,17beta-diol, MFCD00082814, SCHEMBL183700, CHEBI:34386, NSC12458, BDBM50410526, LMST02020105, DB01526, MSK011042-100A, PD008806, Androst-4-ene-3, (3.beta.,17.beta.)-, NS00067942, Q3324829, 4-Androstenediol Solution in Acetonitrile, 100ug/mL, Androst-4-ene-3beta,17beta-diol (?4-Androstenediol), Androst-4-ene-3beta,17beta-diol (Delta4-Androstenediol), (3S,8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol, Androst-4-ene-3beta,17beta-diol; Testosterone Imp. D (EP); Delta4-Androstenediol; Testosterone Impurity D
Theoretical properties:
molecular_formula: C19H30O2
molecular_weight: 290.4 g/mol
exact_mass: 290.224580195 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 21
topological_polar_surface_area: 40.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 4-Androstenediol is a 3-hydroxy steroid. It has a role as an androgen.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 4-Androstenediol, also known as androst-4-ene-3β,17β-diol, is an androstenediol that is converted to testosterone. The conversion rate is about 15.76%, almost triple that of 4-androstenedione, due to utilization of a different enzymatic pathway. There is also some conversion into estrogen, since testosterone is the metabolic precursor of the estrogens.
4-Androstenediol is closer to testosterone structurally than 5-androstenediol, and has androgenic effects, acting as a weak partial agonist of the androgen receptor. However, due to its lower intrinsic activity in comparison, in the presence of full agonists like testosterone or dihydrotestosterone (DHT), 4-androstenediol has antagonistic actions, behaving more like an antiandrogen.
4-Androstenediol is very weakly estrogenic. It has approximately 0.5% and 0.6% of the affinity of estradiol at the ERα and ERβ, respectively.