Compound: 2-HYDROXYESTRONE
SMILES: O=C1[C@@]2([C@H]([C@H]3[C@@H](c4c(cc(O)c(c4)O)CC3)CC2)CC1)C
InChIKey: SWINWPBPEKHUOD-JPVZDGGYSA-N
Synonyms: 2-HYDROXYESTRONE, 362-06-1, Catecholestrone, 2,3-Dihydroxyestra-1,3,5(10)-trien-17-one, UQS3A06ILY, DTXSID80904315, (8R,9S,13S,14S)-2,3-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one, 2-OHE1, CHEBI:1156, 2,3-dihydroxy-estra-1,3,5(10)-trien-17-one, Estra-1,3,5(1)-trien-17-one, 2,3-dihydroxy-, (8R,9S,13S,14S)-2,3-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta(a)phenanthren-17-one, RefChem:87529, Estra-1,3,5(10-trien-17-one, 2,3-dihydroxy)-, DTXCID701333471, 2-OHE(1), 1,3,5(10)-Estratrien-2,3-diol-17-one, 2-Hydroxy Estrone, UNII-UQS3A06ILY, CCRIS 9276, Estra-1,3,5(10)-trien-17-one, 2,3-dihydroxy-; 2,3-Dihydroxyestra-1,3,5(10)-trien-17-one; 2-Hydroxyestrone; Catecholestrone, Estrone Impurity 5, Estra-1,3,5(10)-trien-17-one, 2,3-dihydroxy-, SCHEMBL222517, CHEMBL1627343, SCHEMBL29565251, MSK8578, LMST02010032, MSK8578-100A, AKOS030254485, FH23994, (3aS,3bR,9bS,11aS)-7,8-dihydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-one, PD151132, HY-113251, CS-0059416, NS00006388, C05298, G60992, 2-Hydroxyestrone 100 microg/mL in Acetonitrile, 2-Hydroxy estrone Solution in Acetonitrile, 100ug/mL, Q27105413, 2-Hydroxyestrone; (8R,9S,13S,14S)-2,3-dihydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one
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: 2-hydroxyestrone is a 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2. It has a role as a human metabolite. It is a member of catechols and a 2-hydroxy steroid. It is functionally related to an estrone.
chebi: A 2-hydroxy steroid that is estrone substituted by a hydroxy group at position 2.
chembl: 2-HYDROXYESTRONE 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.