Compound: 16alpha-Hydroxyestrone
SMILES: O=C1[C@@]2([C@H]([C@H]3[C@@H](c4c(cc(O)cc4)CC3)CC2)C[C@H]1O)C
InChIKey: WPOCIZJTELRQMF-QFXBJFAPSA-N
Synonyms: 16alpha-Hydroxyestrone, 566-76-7, 16alpha-OHE1, Hydroxyestrone-16alpha, (8R,9S,13S,14S,16R)-3,16-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one, 3,16alpha-dihydroxy-1,3,5(10)-estratrien-17-one, CHEBI:776, 16 alpha OHE, JY611949JU, 3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-one, J130.683I, C05300, DTXSID901047947, Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-, (16alpha)-, estra-1,3,5(10)-triene-3,16alpha-diol-17-one, (8R,9S,13S,14S,16R)-3,16-DIHYDROXY-13-METHYL-7,8,9,11,12,14,15,16-OCTAHYDRO-6H-CYCLOPENTA(A)PHENANTHREN-17-ONE, 16alpha-OHE, 16alpha-OH Estrone, 16-alphaOHE1, 16alpha-Hydroxy E1, RefChem:1057571, DTXCID201529564, 16alpha-hydroxy estrone, 16|A-Hydroxyestrone, 1,3,5[10]-ESTRATRIENE-3,16ALPHA-DIOL-17-ONE, 16a-Hydroxy Estrone, Estriol EP Impurity H, 1.16a-Hydroxyestrone, 16.alpha.-Hydroxyestrone, (8R,9S,13S,14S,16R)-3,16-Dihydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one, 16a-Hydroxyestrone, 16 alpha-hydroxyestrone, Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy-, (16.alpha.)-, (9beta,13alpha,16beta)-3,16-dihydroxyestra-1,3,5(10)-trien-17-one, 16.alpha.-hydroxy Estrone, UNII-JY611949JU, CCRIS 7200, 3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-one (16alpha-Hydroxyestrone), 3,16a-dihydroxy-estra-1,3,5(10)-trien-17-one, 16.alpha.Ho-oe, 16??-Hydroxyestrone, 16?-Hydroxy Estrone, 3,16-Dihydroxyestra-1,3,5(10)-trien-17-one #, Epitope ID:850769, Estrone, 16alpha-hydroxy-, 16 alpha -Hydroxy Estrone, Estra-1,3,5(10)-triene-3,16a-diol-17-one, 16.ALPHA.-OHE1, SCHEMBL193937, orb3141076, HYDROXYESTRONE [WHO-DD], CHEMBL1233720, SCHEMBL29834891, GTPL12965, MSK8579, LMST02010041, MFCD00870436, MSK8579-100M, AKOS027378621, FH59537, MS-24094, HY-113344, CS-0061863, 3,16a-Dihydroxy-1,3,5(10)-estratrien-17-one, F986899, Q27067422, 16alpha-Hydroxyestrone Solution in Methanol, 100ug/mL, 3,16.alpha.-Dihydroxyestra-1,3,5(10)-trien-17-one, 88B6090E-294B-4358-B2CE-BF627E048AD0, Estra-1,3,5(10)-trien-17-one, 3,16.alpha.-dihydroxy-, 3,16.ALPHA.-DIHYDROXY-1,3,5(10)-ESTRATRIEN-17-ONE, ESTRA-1,3,5(10)-TRIENE-3,16.ALPHA.-DIOL-17-ONE, (16.ALPHA.)-3,16-DIHYDROXYESTRA-1(10),2,4-TRIEN-17-ONE, (16R)-3,16.ALPHA.-DIHYDROXY-1,3,5(10)-ESTRATRIEN-17-ONE, (8R,13S,16R)-3,16-Dihydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one, 16alpha-Hydroxyestrone, 100 mug/mL in methanol, certified reference material, ampule of 1 mL, Estra-1,3,5(10)-trien-17-one, 3,16-dihydroxy- (8CI), Estra-1,3,5(10)-triene-3,16-diol-17-one, 3,16-Dihydroxy-1,3,5(10)-estratrien-17-one, 16-Hydroxyestrone, Estriol Imp. H (EP),(16)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one, (16)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one, J2Z
Theoretical properties:
molecular_formula: C18H22O3
molecular_weight: 286.4 g/mol
exact_mass: 286.15689456 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 21
topological_polar_surface_area: 57.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 16alpha-hydroxyestrone is the 16alpha-hydroxy derivative of estrone; a minor estrogen metabolite. It has a role as an estrogen, a mouse metabolite, a human urinary metabolite and a human blood serum metabolite. It is a 16alpha-hydroxy steroid, a 17-oxo steroid, a secondary alpha-hydroxy ketone and a 3-hydroxy steroid. It is functionally related to an estrone.
chebi: The 16α-hydroxy derivative of estrone; a minor estrogen metabolite.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 2-Hydroxyestrone (2-OHE1), also known as estra-1,3,5(10)-trien-2,3-diol-17-one, is an endogenous, naturally occurring catechol estrogen and a major metabolite of estrone and estradiol. It is formed irreversibly from estrone in the liver and to a lesser extent in other tissues via 2-hydroxylation mediated by cytochrome P450 enzymes, mainly the CYP3A and CYP1A subfamilies. 2-OHE1 is the most abundant catechol estrogen in the body.
2-Hydroxyestrone is not significantly uterotrophic in bioassays, whereas other hydroxylated estrogen metabolites including 2-hydroxyestradiol, 16α-hydroxyestrone, estriol (16α-hydroxyestradiol), 4-hydroxyestradiol, and 4-hydroxyestrone all are. In addition, although not antiestrogenic in the uterus, 2-hydroxyestrone shows antiestrogenic effects on luteinizing hormone and prolactin levels. The lack of estrogenic or antiestrogenic activity of 2-hydroxyestrone in the uterus may be attributable to an extremely high metabolic clearance rate. When incubated at very high concentrations or in combination with a catechol O-methyltransferase (COMT) inhibitor to prevent its metabolism, 2-hydroxyestrone shows antiestrogenic effects in estrogen receptor-positive human breast cancer cells.
2-Hydroxyestrone dissociates from the estrogen receptors much more rapidly than does estradiol.