1.02010-04-08 22:12:35 UTC2020-02-24 19:11:10 UTCFDB016683PruninPrunin, also known as pru du 6.01 protein, prunus, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Prunin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Prunin is a bitter tasting compound found in almond, garden tomato (variety), peach, and pine nut, which makes prunin a potential biomarker for the consumption of these food products. Prunin is a flavanone glycoside found in immature citrus fruits and in tomatoes. Its aglycone form is called naringenin .5,7,4'-Trihydroxyflavanone 7-O-beta-D-glucopyranosideNaringenin 7-O-beta-D-glucosideNaringenin-7-O-glucosidePruninC21H22O10434.3934434.1212969245-hydroxy-2-(4-hydroxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one5-hydroxy-2-(4-hydroxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one529-55-5OCC1OC(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=C(O)C=C2)C(O)C(O)C1OInChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-6,14,16,18-24,26-28H,7-8H2DLIKSSGEMUFQOK-UHFFFAOYSA-N belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.Flavonoid-7-O-glycosidesOrganic compoundsPhenylpropanoids and polyketidesFlavonoidsFlavonoid glycosidesAromatic heteropolycyclic compounds1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoids4'-hydroxyflavonoids5-hydroxyflavonoidsAcetalsAlkyl aryl ethersAryl alkyl ketonesBenzene and substituted derivativesChromonesFlavanonesHexosesHydrocarbon derivativesO-glycosyl compoundsOrganic oxidesOxacyclic compoundsOxanesPhenolic glycosidesPolyolsPrimary alcoholsSecondary alcoholsVinylogous acids1-benzopyran1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoid4'-hydroxyflavonoid5-hydroxyflavonoidAcetalAlcoholAlkyl aryl etherAromatic heteropolycyclic compoundAryl alkyl ketoneAryl ketoneBenzenoidBenzopyranChromaneChromoneEtherFlavanFlavanoneFlavonoid-7-o-glycosideGlycosyl compoundHexose monosaccharideHydrocarbon derivativeHydroxyflavonoidKetoneMonocyclic benzene moietyMonosaccharideO-glycosyl compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxanePhenolPhenolic glycosidePolyolPrimary alcoholSecondary alcoholVinylogous acida flavanone-7-O-β-D-glucosidelogp0.17logs-2.45solubility1.53e+00 g/lmelting_pointMp 225°logp0.57pka_strongest_acidic8.58pka_strongest_basic-3iupac5-hydroxy-2-(4-hydroxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-oneaverage_mass434.3934mono_mass434.121296924smilesOCC1OC(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=C(O)C=C2)C(O)C(O)C1OformulaC21H22O10inchiInChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-6,14,16,18-24,26-28H,7-8H2inchikeyDLIKSSGEMUFQOK-UHFFFAOYSA-Npolar_surface_area166.14refractivity103.43polarizability42.74rotatable_bond_count4acceptor_count10donor_count6physiological_charge0formal_charge0Specdb::CMs57102Specdb::CMs68856Specdb::CMs119165Specdb::CMs123552Specdb::CMs127790Specdb::CMs146782Specdb::CMs826469Specdb::CMs826470Specdb::CMs826471Specdb::CMs826472Specdb::CMs826473Specdb::CMs826474Specdb::CMs826475Specdb::CMs826476Specdb::CMs826477Specdb::CMs826478Specdb::CMs826479Specdb::CMs826480Specdb::CMs826481Specdb::CMs826482Specdb::CMs826483Specdb::CMs826484Specdb::CMs826485Specdb::CMs826486Specdb::CMs826487Specdb::MsMs75240Specdb::MsMs75241Specdb::MsMs75242Specdb::MsMs134844Specdb::MsMs134845Specdb::MsMs134846Specdb::MsMs2226293Specdb::MsMs2228396Specdb::MsMs2228659Specdb::MsMs2230809Specdb::MsMs2230931Specdb::MsMs2233252Specdb::MsMs2233362Specdb::MsMs2235584Specdb::MsMs2236626Specdb::MsMs2237008Specdb::MsMs2238779Specdb::MsMs2238825Specdb::MsMs2240147Specdb::MsMs2240755Specdb::MsMs2241582Specdb::MsMs2242815Specdb::MsMs2243044Specdb::MsMs2299917Specdb::MsMs229991828327AlmondType 1specificPrunus dulcis37550.1672880.16728750.1672875mg/100 gGarden tomato (var.)Type 1specificSolanum lycopersicum var. lycopersicum3977550.1409440.1409436340.140943634mg/100 gPeachType 1specificPrunus persica3760Pine nutType 1specificPinus3337bitter