1.0 2010-04-08 22:09:52 UTC 2019-11-26 03:05:37 UTC FDB011866 Naringin obtained from citrus fruits, Clymenia polyandra (clymenia) and Origanum vulgare (oregano) Naringin is the major flavonoid glycoside in grapefruit and gives grapefruit juice its bitter taste. It is metabolized to the flavonone naringenin in humans. Both naringin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits. Narinigin exerts a variety of pharmacological effects such as antioxidant activity, blood lipid-lowering, anticarcinogenic activity, and inhibition of selected cytochrome P450 enzymes including CYP3A4 and CYP1A2, which may result in several drug interactions in-vitro. Naringin is found in many foods, some of which are fruits, common sage, lime, and citrus. 4'5-DiOH-flavone-7-rhgluc Aurantiin Isohesperidin Naringenin 7-neohesperidoside Naringenin 7-O-[a-L-rhamnosyl-(1->2)-b-D-glucoside] Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside] Naringenin 7-O-[α-L-rhamnosyl-(1->2)-β-D-glucoside] Naringenin 7-O-a-L-rhamnosyl-(1->2)-b-D-glucoside Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucoside Naringenin 7-O-neohesperidoside Naringenin 7-O-α-L-rhamnosyl-(1->2)-β-D-glucoside Naringin Naringin hydrate Naringoside C27H32O14 580.5346 580.179205732 (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one naringin 10236-47-2 C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1 DFPMSGMNTNDNHN-ZPHOTFPESA-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 Disaccharides Flavanones 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 Disaccharide Ether Flavan Flavanone Flavonoid-7-o-glycoside Glycosyl compound Hydrocarbon derivative Hydroxyflavonoid Ketone Monocyclic benzene moiety O-glycosyl compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenolic glycoside Polyol Primary alcohol Secondary alcohol Vinylogous acid dihydroxyflavanone disaccharide derivative flavanones neohesperidoside Liquid logp -0.24 ALOGPS logs -2.16 ALOGPS solubility 4.06e+00 g/l ALOGPS melting_point Mp 171° (dihydrate) logp -0.16 ChemAxon pka_strongest_acidic 8.58 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one ChemAxon average_mass 580.5346 ChemAxon mono_mass 580.179205732 ChemAxon smiles C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]2OC2=CC(O)=C3C(=O)C[C@H](OC3=C2)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O ChemAxon formula C27H32O14 ChemAxon inchi InChI=1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1 ChemAxon inchikey DFPMSGMNTNDNHN-ZPHOTFPESA-N ChemAxon polar_surface_area 225.06 ChemAxon refractivity 134.3 ChemAxon polarizability 56.19 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 14 ChemAxon donor_count 8 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1850 Specdb::CMs 26255 Specdb::CMs 32215 Specdb::CMs 38499 Specdb::CMs 99786 Specdb::CMs 282544 Specdb::CMs 395365 Specdb::CMs 395366 Specdb::CMs 395367 Specdb::CMs 395368 Specdb::CMs 395369 Specdb::CMs 395370 Specdb::CMs 395371 Specdb::CMs 395372 Specdb::CMs 395373 Specdb::CMs 395374 Specdb::CMs 395375 Specdb::CMs 395376 Specdb::CMs 395377 Specdb::CMs 395378 Specdb::CMs 395379 Specdb::CMs 395380 Specdb::CMs 395381 Specdb::CMs 395382 Specdb::CMs 395383 Specdb::CMs 395384 Specdb::MsMs 2169 Specdb::MsMs 5804 Specdb::MsMs 285587 Specdb::MsMs 285588 Specdb::MsMs 285589 Specdb::MsMs 285590 Specdb::MsMs 285591 Specdb::MsMs 285592 Specdb::MsMs 324169 Specdb::MsMs 324170 Specdb::MsMs 324171 Specdb::MsMs 372520 Specdb::MsMs 372521 Specdb::MsMs 372522 Specdb::MsMs 373803 Specdb::MsMs 373804 Specdb::MsMs 373805 Specdb::MsMs 373806 Specdb::MsMs 373807 Specdb::MsMs 373808 Specdb::MsMs 374909 Specdb::MsMs 440293 Specdb::MsMs 440294 Specdb::MsMs 440295 Specdb::MsMs 440296 Specdb::NmrOneD 1915 Specdb::NmrOneD 129078 Specdb::NmrOneD 129079 Specdb::NmrOneD 129080 Specdb::NmrOneD 129081 Specdb::NmrOneD 129082 Specdb::NmrOneD 129083 Specdb::NmrOneD 129084 Specdb::NmrOneD 129085 Specdb::NmrOneD 129086 Specdb::NmrOneD 129087 Specdb::NmrOneD 129088 Specdb::NmrOneD 129089 Specdb::NmrOneD 129090 Specdb::NmrOneD 129091 Specdb::NmrOneD 129092 Specdb::NmrOneD 129093 Specdb::NmrOneD 129094 Specdb::NmrOneD 129095 Specdb::NmrOneD 129096 Specdb::NmrOneD 129097 HMDB02927 28819 #<Reference:0x000055ce30b23c58> #<Reference:0x000055ce30b23960> #<Reference:0x000055ce30b23550> #<Reference:0x000055ce30b22ec0> #<Reference:0x000055ce30b22600> #<Reference:0x000055ce30b22420> #<Reference:0x000055ce30b221c8> #<Reference:0x000055ce30b21f98> Beer Type 2 specific 0.00075 0.00075 0.00075 mg/100 g Citrus Unknown generic Common oregano Type 1 specific Origanum vulgare 39352 Common sage Type 1 specific Salvia officinalis 38868 0.0 0.0 0.0 mg/100 g Common thyme Type 1 specific Thymus vulgaris 49992 0.0 0.0 0.0 mg/100 g Fruit juice Type 2 specific Fruits Unknown generic Grape wine Type 2 specific 0.493 0.753500015 0.232499994 mg/100 g Grapefruit Type 1 specific Citrus X paradisi 37656 34.269336 37.759999355 30.778672656 mg/100 g Grapefruit/Pummelo hybrid Type 1 specific Citrus paradisi X Citrus maxima 37656 45.05 45.049999873 45.049999873 mg/100 g Herbs and Spices Unknown generic Italian oregano Type 1 specific Origanum X majoricum 1384207 0.0 0.0 0.0 mg/100 g Kumquat Type 1 specific Fortunella 2706 Lemon Type 1 specific Citrus limon 2708 0.0 0.0 0.0 mg/100 g Lime Type 1 specific Citrus aurantiifolia 159033 0.0 0.0 0.0 mg/100 g Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 Pomegranate Type 1 specific Punica granatum 22663 Pummelo Type 1 specific Citrus maxima 37334 8.483333 8.48333323 8.48333323 mg/100 g Rosemary Type 1 specific Rosmarinus officinalis 39367 55.049999 55.049999237 55.049999237 mg/100 g Sour orange Type 1 Citrus × aurantium Sweet orange Type 1 specific Citrus sinensis 2711 0.023431 0.070293477 0.0 mg/100 g bitter Aldose reductase inhibitor 40 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). Anti dermatitic 225 A drug used to treat or prevent skin disorders or for the routine care of skin. Anti neuropathic 476 Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-mutagenic 451 Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Anti-viral 689 A substance that destroys or inhibits replication of viruses. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Myorelaxant 1134 Name 936 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. Oviposition stimulant 1181 Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.