1.0 2010-04-08 22:12:35 UTC 2025-11-19 01:49:07 UTC FDB016683 Prunin Prunin, 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-glucopyranoside Naringenin 7-O-beta-D-glucoside Naringenin-7-O-glucoside Prunin C21H22O10 434.3934 434.121296924 5-hydroxy-2-(4-hydroxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one 5-hydroxy-2-(4-hydroxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydro-1-benzopyran-4-one 529-55-5 OCC1OC(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=C(O)C=C2)C(O)C(O)C1O InChI=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,7-8H2 DLIKSSGEMUFQOK-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-glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 4'-hydroxyflavonoids 5-hydroxyflavonoids Acetals Alkyl aryl ethers Aryl alkyl ketones Benzene and substituted derivatives Chromones Flavanones Hexoses Hydrocarbon derivatives O-glycosyl compounds Organic oxides Oxacyclic compounds Oxanes Phenolic glycosides Polyols Primary alcohols Secondary alcohols Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 4'-hydroxyflavonoid 5-hydroxyflavonoid Acetal Alcohol Alkyl aryl ether Aromatic heteropolycyclic compound Aryl alkyl ketone Aryl ketone Benzenoid Benzopyran Chromane Chromone Ether Flavan Flavanone Flavonoid-7-o-glycoside Glycosyl compound Hexose monosaccharide Hydrocarbon derivative Hydroxyflavonoid Ketone Monocyclic benzene moiety Monosaccharide O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenolic glycoside Polyol Primary alcohol Secondary alcohol Vinylogous acid a flavanone-7-O-β-D-glucoside logp 0.17 ALOGPS logs -2.45 ALOGPS solubility 1.53e+00 g/l ALOGPS melting_point Mp 225° logp 0.57 ChemAxon pka_strongest_acidic 8.58 ChemAxon pka_strongest_basic -3 ChemAxon iupac 5-hydroxy-2-(4-hydroxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one ChemAxon average_mass 434.3934 ChemAxon mono_mass 434.121296924 ChemAxon smiles OCC1OC(OC2=CC(O)=C3C(=O)CC(OC3=C2)C2=CC=C(O)C=C2)C(O)C(O)C1O ChemAxon formula C21H22O10 ChemAxon inchi InChI=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,7-8H2 ChemAxon inchikey DLIKSSGEMUFQOK-UHFFFAOYSA-N ChemAxon polar_surface_area 166.14 ChemAxon refractivity 103.43 ChemAxon polarizability 42.74 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 75240 Specdb::MsMs 75241 Specdb::MsMs 75242 Specdb::MsMs 134844 Specdb::MsMs 134845 Specdb::MsMs 134846 Specdb::MsMs 2226293 Specdb::MsMs 2228396 Specdb::MsMs 2228659 Specdb::MsMs 2230809 Specdb::MsMs 2230931 Specdb::MsMs 2233252 Specdb::MsMs 2233362 Specdb::MsMs 2235584 Specdb::MsMs 2236626 Specdb::MsMs 2237008 Specdb::MsMs 2238779 Specdb::MsMs 2238825 Specdb::MsMs 2240147 Specdb::MsMs 2240755 Specdb::MsMs 2241582 Specdb::MsMs 2242815 Specdb::MsMs 2243044 Specdb::MsMs 2299917 Specdb::MsMs 2299918 Specdb::CMs 57102 Specdb::CMs 68856 Specdb::CMs 119165 Specdb::CMs 123552 Specdb::CMs 127790 Specdb::CMs 146782 Specdb::CMs 826469 Specdb::CMs 826470 Specdb::CMs 826471 Specdb::CMs 826472 Specdb::CMs 826473 Specdb::CMs 826474 Specdb::CMs 826475 Specdb::CMs 826476 Specdb::CMs 826477 Specdb::CMs 826478 Specdb::CMs 826479 Specdb::CMs 826480 Specdb::CMs 826481 Specdb::CMs 826482 Specdb::CMs 826483 Specdb::CMs 826484 Specdb::CMs 826485 Specdb::CMs 826486 Specdb::CMs 826487 28327 Almond Type 1 specific Prunus dulcis 3755 0.167288 0.1672875 0.1672875 mg/100 g Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 0.140944 0.140943634 0.140943634 mg/100 g Peach Type 1 specific Prunus persica 3760 Pine nut Type 1 specific Pinus 3337 bitter