Compound: Estriol 3-glucuronide
SMILES: O=C(O)[C@H]1O[C@@H](Oc2cc3c([C@@H]4[C@H]([C@H]5[C@]([C@@H](O)[C@@H](C5)O)(C)CC4)CC3)cc2)[C@H](O)[C@H]([C@@H]1O)O
InChIKey: UZKIAJMSMKLBQE-JRSYHJKYSA-N
Synonyms: Estriol 3-glucuronide, 2479-91-6, (16alpha,17beta)-16,17-Dihydroxyestra-1,3,5(10)-trien-3-yl beta-D-glucopyranosiduronic acid, RefChem:79065, (16 alpha,17 beta)-16,17-dihydroxyestra-1,3,5(10)-trien-3-yl beta-D-glucopyranosiduronic acid, 16alpha,17beta-Estriol 3-(beta-D-glucuronide), estriol 3-O-(beta-D-glucuronide), ESTRIOL 3-(B-D-GLUCURONIDE), (2S,3S,4S,5R,6S)-6-[[(8R,9S,13S,14S,16R,17R)-16,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid, CHEBI:45869, estra-1,3,5(10)-triene-3,16alpha,17beta-triol 3-D-glucuronide, Estriol 3-?-D-Glucuronide (sodium salt), DTXSID60947700, Epitope ID:159254, E13G, orb1692834, SCHEMBL4261172, CHEMBL1236070, LMST05010017, AKOS027461010, FS-6919, HY-113169, CS-0062331, Q27120636, 16alpha,17beta-Dihydroxyestra-1(10),2,4-trien-3-yl beta-D-glucopyranosiduronic acid, (14beta,16alpha,17alpha)-16,17-dihydroxyestra-1,3,5(10)-trien-3-yl beta-D-glucopyranosiduronic acid, (2S,3S,4S,5R,6S)-6-(((8R,9S,13S,14S,16R,17R)-16,17-dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)oxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid
Theoretical properties:
molecular_formula: C24H32O9
molecular_weight: 464.5 g/mol
exact_mass: 464.20463259 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 3
heavy_atom_count: 33
topological_polar_surface_area: 157 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
{"pubchem": "Estriol 3-O-(beta-D-glucuronide) is a steroid glucosiduronic acid that is the 3-beta-D-glucuronide of estriol; a steroid hormone ligand recognised by the monoclonal antibody 4155. It has a role as an estrogen and an epitope. It is a 16alpha-hydroxy steroid, a steroid glucosiduronic acid and a 17beta-hydroxy steroid. It is functionally related to an estriol. It is a conjugate acid of an estriol 3-O-(beta-D-glucuronide)(1-). It derives from a hydride of an estrane.", "chebi": "A  steroid glucosiduronic acid that is the 3-\u03b2-<small>D</small>-glucuronide of estriol; a steroid hormone ligand recognised by the monoclonal antibody 4155.", "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Estriol glucuronide (E3G), or oestriol glucuronide, also known as estriol monoglucuronide, as well as estriol 16\u03b1-\u03b2-D-glucosiduronic acid, is a natural, steroidal estrogen and the glucuronic acid (\u03b2-D-glucopyranuronic acid) conjugate of estriol. It occurs in high concentrations in the urine of pregnant women as a reversibly formed metabolite of estriol. Estriol glucuronide is a prodrug of estriol, and was the major component of Progynon and Emmenin, estrogenic products manufactured from the urine of pregnant women that were introduced in the 1920s and 1930s and were the first orally active estrogens. Emmenin was succeeded by Premarin (conjugated equine estrogens), which is sourced from the urine of pregnant mares and was introduced in 1941. Premarin replaced Emmenin because it was easier and less expensive to produce.\nEstrogen glucuronides can be deglucuronidated into the corresponding free estrogens by \u03b2-glucuronidase in tissues that express this enzyme, such as the mammary gland. As a result, estrogen glucuronides have estrogenic activity via conversion into estrogens.\nThe positional isomer of estriol 16\u03b1-glucuronide, estriol 3-glucuronide, also occurs as an endogenous metabolite of estriol, although to a much lower extent in comparison."}