Compound: Morphine-3-glucuronide
SMILES: O=C(O)[C@H]1O[C@@H](Oc2c3O[C@H]4[C@@H](O)C=C[C@@H]5[C@]64c3c(C[C@H]5N(C)CC6)cc2)[C@H](O)[C@H]([C@@H]1O)O
InChIKey: WAEXKFONHRHFBZ-ZXDZBKESSA-N
Synonyms: Morphine-3-glucuronide, 20290-09-9, O27Z9CH39A, DTXSID80174157, (2S,3S,4S,5R,6S)-6-[[(4R,4aR,7S,7aR,12bS)-7-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid, beta-D-Glucopyranosiduronic acid, (5alpha,6alpha)-7,8-didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl, (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(((1S,5R,13R,14S,17R)-14-hydroxy-4-methyl-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7(18),8,10,15-tetraen-10-yl)oxy)oxane-2-carboxylic acid, (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-14-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-10-yl]oxy}oxane-2-carboxylic acid, (2S,3S,4S,5R,6S)-6-(((4R,4aR,7S,7aR,12bS)-7-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolin-9-yl)oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid, RefChem:819441, (-)-Morphine 3-glucuronide, DTXCID5096648, Morphine-3-beta-D-glucuronide, CHEBI:80631, Morphine 3-beta-D-glucuronide, UNII-O27Z9CH39A, Morphine 3-b-D-Glucuronide (0.1 mg/mL in Methanol/Water 1:1), Morphine 3-b-D-Glucuronide (1.0 mg/mL in Methanol w/0.05% NaOH), Morphine-3G, .beta.-D-Glucopyranosiduronic acid, (5.alpha.,6.alpha.)-7,8-didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl, morphine-3-beta-glucuronide, CHEMBL1329, Epitope ID:2270999, Morphine 3-?-D-Glucuronide, Morfina 3beta- D-Glucuronide, SCHEMBL3843209, BDBM224029, MORPHINE 3-GLUCURONIDE(MINOR), .BETA.-D-GLUCOPYRANOSIDURONIC ACID, MORPHINE 3-O-.BETA.-D-GLUCURONIDE, NS00007611, Q65707098, GLUCOPYRANOSIDURONIC ACID, MORPHINE-3, .BETA.-D-, Morphine 3-beta-D-Glucuronide (1 mg/mL in Methanol w/0.05% NaOH), Morphine-3-Beta-D-glucuronide, 1mg/ml in Methanol/Water : 1/1, (5?,6?)-7,8-Didehydro-4,5-epoxy-6-hydroxy-17-methylmorphinan-3-yl ?-d-Glucopyranosiduronic Acid; 3-Glucuronosidomorphine; Morphine 3-O-Glucuronide;, 6alpha-Hydroxy-17-methyl-5alpha-7,8-didehydro-4,5-epoxymorphinan-3-yl beta-D-glucopyranosiduronic acid
Theoretical properties:
molecular_formula: C23H27NO9
molecular_weight: 461.5 g/mol
exact_mass: 461.16858144 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 10
rotatable_bond_count: 3
heavy_atom_count: 33
topological_polar_surface_area: 149 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Morphine-3-glucuronide is a morphinane alkaloid.
chembl: MORPHINE 3-GLUCURONIDE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Morphine-3-glucuronide is a metabolite of morphine produced by UGT2B7.  It is not active as an opioid agonist, but does have some action as a convulsant, which does not appear to be mediated through opioid receptors, but rather through interaction with glycine and/or GABA receptors. As a polar compound, it has a limited ability to cross the blood–brain barrier, but kidney failure may lead to its accumulation and result in seizures. Probenecid and inhibitors of P-glycoprotein can enhance uptake of morphine-3-glucuronide and, to a lesser extent, morphine-6-glucuronide. Reported side effects related to the accumulation of this metabolite include convulsions, agitation, hallucinations, hyperalgesia, and coma.