Compound: Phellamurin
SMILES: O=C1c2c(O[C@@H]([C@H]1O)c3ccc(O)cc3)c(c(O[C@@H]4O[C@@H]([C@@H](O)[C@@H]([C@H]4O)O)CO)cc2O)CC=C(C)C
InChIKey: GRDZTDZJQRPNCN-YIANMRPHSA-N
Synonyms: Phellamurin, 52589-11-4, Fellavine, 8-Prenyldihydrokaempferol 7-glucoside, UXB86HY2NK, CHEBI:8048, (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one, DTXSID00200563, 3,4',5,7-Tetrahydroxy-8-isoprenylflavanone-7-O-glucoside, (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chroman-4-one, 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-2,3-dihydro-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-, (2R-trans)-, (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2,3-dihydrochromen-4-one, (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl)oxy-chroman-4-one, RefChem:172511, DTXCID30123054, Fellavin; Flacoside, (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one, C26H30O11, MFCD00869630, FELLAVIN, FLACOSIDE, UNII-UXB86HY2NK, CHEMBL516116, MEGxp0_002039, orb1297078, SCHEMBL27013577, SCHEMBL30291874, ACon1_000824, HY-N3085, AKOS015955752, EBC-615953, FS-9972, NCGC00169323-01, (2R,3R)-3,5-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one, DA-76798, CS-0023185, C09808, Q7181228, BRD-K05031216-001-01-3, (2R,3R)-3,5-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl beta-D-glucopyranoside, (2R,3R)-7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-3,5-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-4H-1-BENZOPYRAN-4-ONE, 4H-1-BENZOPYRAN-4-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-3,5-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-, (2R,3R)-, 4H-1-BENZOPYRAN-4-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-3,5-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTENYL)-, (2R,3R)-, 4H-1-BENZOPYRAN-4-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-3,5-DIHYDROXY-2-(4-HYDROXYPHENYL)-8-(3-METHYL-2-BUTENYL)-, (2R-TRANS)-
Theoretical properties:
molecular_formula: C26H30O11
molecular_weight: 518.5 g/mol
exact_mass: 518.17881177 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 7
hydrogen_bond_acceptor_count: 11
rotatable_bond_count: 6
heavy_atom_count: 37
topological_polar_surface_area: 186 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Phellamurin is a member of the class of dihydroflavonols that is (+)-dihydrokaempferol substituted by a prenyl group at position 8 and a beta-D-glucopyranosyl group at position 7 via a glycosidic linkage. Isolated from Phellodendron amurense and Commiphora africana, it exhibits inhibition of intestinal P-glycoprotein. It has a role as a metabolite. It is a member of 4'-hydroxyflavanones, a beta-D-glucoside, a trihydroxyflavanone, a member of dihydroflavonols, a monosaccharide derivative and a flavanone glycoside. It is functionally related to a (+)-dihydrokaempferol.
chebi: A member of the class of dihydroflavonols that is (+)-dihydrokaempferol substituted by a prenyl group at position 8 and a β-<small>D</small>-glucopyranosyl group at position 7 via a glycosidic linkage. Isolated from   <em>Phellodendron amurense</em> and <em>Commiphora africana</em>, it exhibits inhibition of intestinal P-glycoprotein.
chembl: PHELLAMURIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Phellamurin, a flavonoid, is the 7-O-β-D-glucopyranoside, 8-C-prenyl derivative of the flavan-on-ol Aromadendrin, and may be seen as the 7-O-glucoside of noricaritin. Being a flavanonol, it has two stereocenters on the C-ring, so four stereoisomers of phellamurin are possible.
It can be found in Commiphora africana and in Phellodendron amurense.