1.0 2010-04-08 22:09:52 UTC 2026-09-18 18:02:59 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::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 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::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 HMDB02927 28819 #<Reference:0x0000558be9813038> #<Reference:0x0000558be9812e58> #<Reference:0x0000558be9812ca0> #<Reference:0x0000558be98129a8> #<Reference:0x0000558be98127c8> #<Reference:0x0000558be98125e8> #<Reference:0x0000558be98122f0> #<Reference:0x0000558be9812138> 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 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 Plant Citrus limon 2708 0.0 0.0 0.0 mg/100 g Lime Type 1 Plant Citrus aurantiifolia 159033 0.0 0.0 0.0 mg/100 g Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 Melogold Type 1 Plant Citrus paradisi X Citrus maxima 37656 45.05 45.049999873 45.049999873 mg/100 g 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 Acetyl-coenzyme A transporter 1 O00400 SLC33A1 Adenylate kinase 2, mitochondrial P54819 AK2 Cathepsin K P43235 CTSK Cytochrome P450 2A6 P11509 CP2A6_HUMAN CYP2A6 Focal adhesion kinase 1 Q05397 PTK2 L-ascorbate peroxidase 1, cytosolic Q10N21 APX1_ORYSJ APX1 Proactivator polypeptide P07602 PSAP Sterol O-acyltransferase 1 P35610 SOAT1 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). Alpha-glucosidase inhibitor 45 An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-glucosidase (EC 3.2.1.20). Anabolic 54 A compound which stimulates anabolism and inhibits catabolism. Anabolic agents stimulate the development of muscle mass, strength, and power. Analgesic 56 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti carcinogenic 161 A substance that inhibits or prevents the proliferation of neoplasms. Anti convulsant 204 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti depressant 223 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti dermatitic 225 A drug used to treat or prevent skin disorders or for the routine care of skin. Anti hypercholesterolemic 342 Anti hyperglycemic 343 Anti hyperlipidemic 348 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti hypertensive 352 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti hypoglycemic 355 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti lipedemic 403 Anti lipogenic 405 Anti microbial 436 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti neuropathic 476 Anti osteoporotic 495 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti peroxidative 520 Anti ulcer 676 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. Anti-aging 95 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-allergic 103 A drug used to treat allergic reactions. Anti-apoptotic 125 Anti-atherogenic 136 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. Anti-atherosclerotic 138 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. Anti-cancer 159 A substance that inhibits or prevents the proliferation of neoplasms. Anti-cholesterogenic 182 Anti-diabetic 228 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-infective 368 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-mutagenic 451 Anti-mutilation 452 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-proliferative 548 Anti-tussive 674 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-viral 689 A substance that destroys or inhibits replication of viruses. Anti-Zika virus 1441 Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Anxiolytic 698 Anxiolytic drugs are agents that alleviate anxiety, tension, and anxiety disorders, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. Bacteriostatic 724 A substance that kills or slows the growth of bacteria. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Cardioprotective 769 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. DNA-protective 887 Edematogenic 1836 Estrogenic 922 Flavor 936 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. Gastroprotective 947 A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion. Genoprotective 2131 Hepatoprotective 981 Any compound that is able to prevent damage to the liver. Hepatotoxic 984 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals. Hyperglycemic 1005 A drug which increases the blood glucose level. Hypocholesterolemic 1016 Hypolipemic 1019 Hypolipidemic 1020 Immunomodulator 1031 Biologically active substance whose activity affects or plays a role in the functioning of the immune system. Inhibitor 1432 A substance that diminishes the rate of a chemical reaction. Insulin-Mimetic 1477 Lipolytic 1074 Myorelaxant 1134 Nephroprotective 1147 Any protective agent that is able to prevent damage to the kidney. Neuroprotective 1158 Any compound that can be used for the treatment of neurodegenerative disorders. Neurotoxic 1160 A poison that interferes with the functions of the nervous system. 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. Prebiotic 1240 Proteolytic 1265 Sedative 1311 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. Ulcerprotective 2113