Compound: Prunetin
SMILES: O=c1c2c(occ1-c3ccc(O)cc3)cc(OC)cc2O
InChIKey: KQMVAGISDHMXJJ-UHFFFAOYSA-N
Synonyms: Prunetin, 552-59-0, Prunusetin, 5,4'-dihydroxy-7-methoxyisoflavone, 4',5-dihydroxy-7-methoxyisoflavone, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one, 5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one, 1TG4H5H11J, DTXSID3022530, RefChem:930127, DTXCID102530, 209-018-5, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one, Padmakastein, 4H-1-Benzopyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-, 5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4-benzopyrone, MFCD00016951, EINECS 209-018-5, BRN 0292155, pruneitin, UNII-1TG4H5H11J, CCRIS 8951, 7-O-methyl-genistein, 7-O-Methyl genistein, Spectrum_001027, SpecPlus_000493, PRUNETIN [MI], Spectrum3_001402, Spectrum4_001723, Spectrum5_000486, Oprea1_083784, SCHEMBL73420, BSPBio_003044, KBioGR_002106, KBioSS_001507, 5-18-04-00595 (Beilstein Handbook Reference), BIDD:ER0153, DivK1c_006589, Isoflavone, 4',5-dihydroxy-7-methoxy- (7CI,8CI), CHEMBL491174, GTPL6919, orb1302338, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-chromen-4-one, SCHEMBL29612430, KBio1_001533, KBio2_001507, KBio2_004075, KBio2_006643, KBio3_002264, Prunetin, >=98.0% (TLC), 4',5-dihydroxy-7-methoxygenistein, HY-N2597, BDBM50359990, LMPK12050353, AKOS016010281, EBC-465073, FP66156, SMP1_000150, Isoflavone, 4',5-dihydroxy-7-methoxy-, NCGC00178331-01, AC-35016, AS-71541, DA-57174, ST096009, CS-0022974, NS00033278, F241347, Q7253051, BRD-K57546357-001-01-6, 5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one, 9CI
Theoretical properties:
molecular_formula: C16H12O5
molecular_weight: 284.26 g/mol
exact_mass: 284.06847348 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 21
topological_polar_surface_area: 76 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 246 - 248 °C
Descriptions:
pubchem: Prunetin is a hydroxyisoflavone that is genistein in which the hydroxy group at position 7 is replaced by a methoxy group. It has a role as a metabolite, an EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor, an EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor and an anti-inflammatory agent. It is a member of 7-methoxyisoflavones and a hydroxyisoflavone. It is functionally related to a genistein. It is a conjugate acid of a prunetin-5-olate.
chebi: A hydroxyisoflavone that is  genistein  in which the hydroxy group at position 7 is replaced by a methoxy group.
chembl: PRUNETIN is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Prunetin is an O-methylated isoflavone, a type of flavonoid. It has been isolated for the first time by Finnemore in 1910 in the bark of Prunus emarginata (the Oregon cherry). Prunetin isolated from pea roots can act as an attractant for Aphanomyces euteiches zoospores. It is also an allosteric inhibitor of human liver aldehyde dehydrogenase.
Prunetin can lower blood pressure of spontaneously hypertensive rats and relax isolated rat aortic rings through calcium channel block mechanisms in vessel smooth muscles.