Compound: Estrone 3-glucuronide
SMILES: O=C1[C@@]2([C@H]([C@H]3[C@@H](c4c(cc(O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@@H]([C@H]5O)O)cc4)CC3)CC2)CC1)C
InChIKey: FJAZVHYPASAQKM-JBAURARKSA-N
Synonyms: Estrone 3-glucuronide, 2479-90-5, Estrone glucuronide, Estrone-3-glucuronide, ESTRONE BETA-D-GLUCURONIDE, Estrone-3-glucosiduronate, DTXSID20891497, 933Q277TO2, (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]oxane-2-carboxylic acid, 3-hydroxy-estra-1,3,5(10)-trien-17-one 3-D-glucuronide, beta-D-Glucopyranosiduronic acid, 17-oxoestra-1,3,5(10)-trien-3-yl, (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta(a)phenanthren-3-yl)oxy)oxane-2-carboxylic acid, RefChem:921188, DTXCID501030598, 17-oxoestra-1,3,5(10)-trien-3-yl beta-D-glucopyranosiduronic acid, .beta.-D-Glucopyranosiduronic acid, 17-oxoestra-1,3,5(10)-trien-3-yl, E3G, UNII-933Q277TO2, Estrone Impurity 11, estrone 3-glucosiduronic acid, Estrone-3-glucosiduronic acid, Estrone-3-Glucuronide (Estrone beta-D-Glucuronide), Estrone beta-delta-glucuronide, orb1983473, SCHEMBL2505282, CHEMBL1232444, SCHEMBL29380869, CHEBI:28919, Estrone-3-(beta-D-glucuronide), ESTRONE MONOGLUCOSIDURONATE, ESTRONE .BETA.-GLUCURONIDE, ESTRONE .BETA.-D-GLUCURONIDE, LMST05010011, B-D-GLUCOPYRANOSIDURONIC ACID,17-OXOESTRA-1,3,5(10)-TRIEN-3-YL, PD150771, HY-113157, CS-0062306, NS00014415, Q27271553, .BETA.-D-GLUCOSIDURONIC ACID, 17-OXOESTRA-1,3,5(10)-TRIEN-3-YL, (14beta)-17-oxoestra-1,3,5(10)-trien-3-yl beta-D-glucopyranosiduronic acid, 1,3,5(10)-ESTRATRIEN-3-OL-17-ONE 3(O->1BETA)-D-GLYCOPYRANOSIDURONIC ACID, ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-(.BETA.-D-GLUCOPYRANURONOSYLOXY)-, GLUCOPYRANOSIDURONIC ACID, 17-OXOESTRA-1,3,5(10)-TRIEN-3-YL, .BETA.-D-, (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid, (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]oxy]tetrahydropyran-2-carboxylic acid
Theoretical properties:
molecular_formula: C24H30O8
molecular_weight: 446.5 g/mol
exact_mass: 446.19406791 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 8
rotatable_bond_count: 3
heavy_atom_count: 32
topological_polar_surface_area: 134 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 254.5 °C
Descriptions:
{"pubchem": "Estrone 3-O-(beta-D-glucuronide) is the 3-beta-D-glucuronide of estrone. It has a role as a mouse metabolite and a human metabolite. It is a beta-D-glucosiduronic acid, a 17-oxo steroid and a steroid glucosiduronic acid. It is functionally related to an estrone. It is a conjugate acid of an estrone 3-O-(beta-D-glucuronide)(1-).", "chebi": "The 3-\u03b2-<small>D</small>-glucuronide of estrone.", "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Estrone glucuronide, or estrone-3-D-glucuronide, is a conjugated metabolite of estrone. It is formed from estrone in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by the kidneys. It has much higher water solubility than does estrone. Glucuronides are the most abundant estrogen conjugates and estrone glucuronide is the dominant metabolite of estradiol.\nWhen exogenous estradiol is administered orally, it is subject to extensive first-pass metabolism (95%) in the intestines and liver. A single administered dose of estradiol is absorbed 15% as estrone, 25% as estrone sulfate, 25% as estradiol glucuronide, and 25% as estrone glucuronide. Formation of estrogen glucuronide conjugates is particularly important with oral estradiol as the percentage of estrogen glucuronide conjugates in circulation is much higher with oral ingestion than with parenteral estradiol. Estrone glucuronide can be reconverted back into estradiol, and a large circulating pool of estrogen glucuronide and sulfate conjugates serves as a long-lasting reservoir of estradiol that effectively extends its terminal half-life of oral estradiol. In demonstration of the importance of first-pass metabolism and the estrogen conjugate reservoir in the pharmacokinetics of estradiol, the terminal half-life of oral estradiol is 13 to 20 hours whereas with intravenous injection its terminal half-life is only about 1 to 2 hours."}