1.02010-04-08 22:09:52 UTC2019-11-26 03:05:37 UTCFDB011866Naringinobtained 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-rhglucAurantiinIsohesperidinNaringenin 7-neohesperidosideNaringenin 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-glucosideNaringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucosideNaringenin 7-O-neohesperidosideNaringenin 7-O-α-L-rhamnosyl-(1->2)-β-D-glucosideNaringinNaringin hydrateNaringosideC27H32O14580.5346580.179205732(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-onenaringin10236-47-2C[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]1OInChI=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/s1DFPMSGMNTNDNHN-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-glycosidesOrganic compoundsPhenylpropanoids and polyketidesFlavonoidsFlavonoid glycosidesAromatic heteropolycyclic compounds1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoids4'-hydroxyflavonoids5-hydroxyflavonoidsAcetalsAlkyl aryl ethersAryl alkyl ketonesBenzene and substituted derivativesChromonesDisaccharidesFlavanonesHydrocarbon 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 ketoneBenzenoidBenzopyranChromaneChromoneDisaccharideEtherFlavanFlavanoneFlavonoid-7-o-glycosideGlycosyl compoundHydrocarbon derivativeHydroxyflavonoidKetoneMonocyclic benzene moietyO-glycosyl compoundOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacycleOxanePhenolPhenolic glycosidePolyolPrimary alcoholSecondary alcoholVinylogous aciddihydroxyflavanonedisaccharide derivativeflavanonesneohesperidosideLiquidlogp-0.24logs-2.16solubility4.06e+00 g/lmelting_pointMp 171° (dihydrate)logp-0.16pka_strongest_acidic8.58pka_strongest_basic-3.6iupac(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-oneaverage_mass580.5346mono_mass580.179205732smilesC[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]1OformulaC27H32O14inchiInChI=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/s1inchikeyDFPMSGMNTNDNHN-ZPHOTFPESA-Npolar_surface_area225.06refractivity134.3polarizability56.19rotatable_bond_count6acceptor_count14donor_count8physiological_charge0formal_charge0Specdb::NmrTwoD1850Specdb::NmrOneD1915Specdb::NmrOneD129078Specdb::NmrOneD129079Specdb::NmrOneD129080Specdb::NmrOneD129081Specdb::NmrOneD129082Specdb::NmrOneD129083Specdb::NmrOneD129084Specdb::NmrOneD129085Specdb::NmrOneD129086Specdb::NmrOneD129087Specdb::NmrOneD129088Specdb::NmrOneD129089Specdb::NmrOneD129090Specdb::NmrOneD129091Specdb::NmrOneD129092Specdb::NmrOneD129093Specdb::NmrOneD129094Specdb::NmrOneD129095Specdb::NmrOneD129096Specdb::NmrOneD129097Specdb::CMs26255Specdb::CMs32215Specdb::CMs38499Specdb::CMs99786Specdb::CMs282544Specdb::CMs395365Specdb::CMs395366Specdb::CMs395367Specdb::CMs395368Specdb::CMs395369Specdb::CMs395370Specdb::CMs395371Specdb::CMs395372Specdb::CMs395373Specdb::CMs395374Specdb::CMs395375Specdb::CMs395376Specdb::CMs395377Specdb::CMs395378Specdb::CMs395379Specdb::CMs395380Specdb::CMs395381Specdb::CMs395382Specdb::CMs395383Specdb::CMs395384Specdb::MsMs2169Specdb::MsMs5804Specdb::MsMs285587Specdb::MsMs285588Specdb::MsMs285589Specdb::MsMs285590Specdb::MsMs285591Specdb::MsMs285592Specdb::MsMs324169Specdb::MsMs324170Specdb::MsMs324171Specdb::MsMs372520Specdb::MsMs372521Specdb::MsMs372522Specdb::MsMs373803Specdb::MsMs373804Specdb::MsMs373805Specdb::MsMs373806Specdb::MsMs373807Specdb::MsMs373808Specdb::MsMs374909Specdb::MsMs440293Specdb::MsMs440294Specdb::MsMs440295Specdb::MsMs440296HMDB0292728819#<Reference:0x00005556755d1d28>#<Reference:0x00005556755d1b20>#<Reference:0x00005556755d18f0>#<Reference:0x00005556755d16c0>#<Reference:0x00005556755d1490>#<Reference:0x00005556755d1238>#<Reference:0x00005556755d1058>#<Reference:0x00005556755d0e28>BeerType 2specific0.000750.000750.00075mg/100 gCitrusUnknowngenericCommon oreganoType 1specificOriganum vulgare39352Common sageType 1specificSalvia officinalis388680.00.00.0mg/100 gCommon thymeType 1specificThymus vulgaris499920.00.00.0mg/100 gFruit juiceType 2specificFruitsUnknowngenericGrape wineType 2specific0.4930.7535000150.232499994mg/100 gGrapefruitType 1specificCitrus X paradisi3765634.26933637.75999935530.778672656mg/100 gGrapefruit/Pummelo hybridType 1specificCitrus paradisi X Citrus maxima3765645.0545.04999987345.049999873mg/100 gHerbs and SpicesUnknowngenericItalian oreganoType 1specificOriganum X majoricum13842070.00.00.0mg/100 gKumquatType 1specificFortunella2706LemonType 1specificCitrus limon27080.00.00.0mg/100 gLimeType 1specificCitrus aurantiifolia1590330.00.00.0mg/100 gMandarin orange (Clementine, Tangerine)Type 1specificCitrus reticulata85571PomegranateType 1specificPunica granatum22663PummeloType 1specificCitrus maxima373348.4833338.483333238.48333323mg/100 gRosemaryType 1specificRosmarinus officinalis3936755.04999955.04999923755.049999237mg/100 gSour orangeType 1Citrus × aurantiumSweet orangeType 1specificCitrus sinensis27110.0234310.0702934770.0mg/100 gbitteraldose reductase inhibitor40An 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 dermatitic225A drug used to treat or prevent skin disorders or for the routine care of skin.anti inflammatory370A substance that reduces or suppresses inflammation.anti mutagenic451anti neuropathic476anti viral689A substance that destroys or inhibits replication of viruses.antioxidant502A 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.cancer preventive754A substance that inhibits or prevents the proliferation of neoplasms.flavor936A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.myorelaxant1134oviposition stimulant1181pesticide1210Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.