Compound: 16alpha-Hydroxyandrostenedione
SMILES: O=C1C=C2[C@]([C@@H]3[C@H]([C@H]4[C@](C(=O)[C@@H](C4)O)(C)CC3)CC2)(C)CC1
InChIKey: SSBCZTXGVMMZOT-NBBHSKLNSA-N
Synonyms: 16alpha-Hydroxyandrostenedione, 63-02-5, 16alpha-Hydroxyandrost-4-ene-3,17-dione, 16alpha-OH-Adion, JN8H7214IR, 16alpha-hydroxy-4-androstene-3,17-dione, delta4-Androsten-3,17-dione-16alpha-ol, (16alpha)-16-Hydroxyandrost-4-ene-3,17-dione, 4-Androsten-16alpha-ol-3,17-dione, CHEBI:27582, DTXSID20331500, RefChem:908224, DTXCID30282594, UNII-JN8H7214IR, (8R,9S,10R,13S,14S,16R)-16-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione, 16?-Hydroxyandrostenedione, 4-ANDROSTEN-16A-OL-3,17-DIONE, C05140, 16.ALPHA.-OH-ADION, 16alpha-hydroxy-androstenedione, SCHEMBL2508757, CHEMBL1908014, Androst-4-ene-3,17-dione, 16-hydroxy-, (16.alpha.)-, LMST02020065, 16.ALPHA.-HYDROXYANDROSTENEDIONE, 16a-Hydroxyandrost-4-ene-3,17-dione, 16alpha-hydroxy-androst-4-ene-3,17-dione, 16.ALPHA.-HYDROXY-4-ANDROSTENE-3,17-DIONE, .DELTA.4-ANDROSTEN-3,17-DIONE-16.ALPHA.-OL, Q27103209, (16.ALPHA.)-16-HYDROXYANDROST-4-ENE-3,17-DIONE
Theoretical properties:
molecular_formula: C19H26O3
molecular_weight: 302.4 g/mol
exact_mass: 302.18819469 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 22
topological_polar_surface_area: 54.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "16alpha-hydroxyandrost-4-ene-3,17-dione is a 16alpha-hydroxy steroid, a 17-oxo steroid, a secondary alpha-hydroxy ketone, a 3-oxo steroid and an androstanoid. It has a role as a mouse metabolite.", "chebi": null, "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "16\u03b1-Hydroxyestrone (16\u03b1-OH-E1), or hydroxyestrone, also known as estra-1,3,5(10)-triene-3,16\u03b1-diol-17-one, is an endogenous steroidal estrogen and a major metabolite of estrone, as well as an intermediate in the biosynthesis of estriol. It is a potent estrogen similarly to estrone, and it has been suggested that the ratio of 16\u03b1-hydroxyestrone to 2-hydroxyestrone, the latter being much less estrogenic in comparison and even antiestrogenic in the presence of more potent estrogens like estradiol, may be involved in the pathophysiology of breast cancer. Conversely, 16\u03b1-hydroxyestrone may help to protect against osteoporosis.\nIn terms of relative binding affinity (RBA) for the rat uterine estrogen receptor, 16\u03b1-hydroxyestrone showed 2.8% of the affinity of estradiol. For comparison, estrone had 11% of the affinity and estriol had 10% of the affinity of estradiol. In contrast to other estrogens, the binding  of 16\u03b1-hydroxyestrone to the estrogen receptor is reported to be covalent and irreversible. 16\u03b1-Hydroxyestrone has been reported to have 25% of the vaginal estrogenic potency of estradiol. The maximal uterotrophic and antigonadotropic effect of 16\u03b1-hydroxyestrone was equivalent to those of estradiol and estriol, indicating that 16\u03b1-hydroxyestrone is a fully effective estrogen. However, 16\u03b1-hydroxyestrone was much less potent than estradiol or estrone.\nThe C3 and C16\u03b1 diacetate ester of 16\u03b1-hydroxyestrone, hydroxyestrone diacetate (brand names Colpoginon, Colpormon, Hormobion, and Hormocervix), has been marketed and used medically as an estrogen in Europe."}