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Record Information
Version1.0
Created at2006-05-22 15:12:02 UTC
Updated at2021-10-07 20:41:39 UTC
NP-MRD IDNP0001313
Secondary Accession NumbersNone
Natural Product Identification
Common NameNaringenin
DescriptionNaringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs. Naringenin has the skeleton structure of a flavanone with three hydroxy groups at the 4', 5, and 7 carbons. It may be found both in the aglycol form, naringenin, or in its glycosidic form, naringin, which has the addition of the disaccharide neohesperidose attached via a glycosidic linkage at carbon 7. Naringenin (not to be confused with naringin) is a flavanone that is considered to have a bioactive effect on human health as antioxidant, free radical scavenger, antiinflammatory, carbohydrate metabolism promoter, immunity system modulater. This substance has also been shown to repair DNA. Scientists exposed cells to 80 micomoles of naringenin per liter, for 24 hours, and found that the amount of hydroxyl damage to the DNA was reduced by 24 percent in that very short period of time. Unfortunately, this bioflavonoid is difficult to absorb on oral ingestion. Only 15% of ingested naringenin will get absorbed, in the human gastrointestinal tract, in the best case scenario. A full glass of orange juice will supply about enough naringenin to achieve a concentration of about 0.5 Micromoles per liter. Naringenin is a biomarker for the consumption of citrus fruits.
Structure
Thumb
Synonyms
ValueSource
(-)-(2S)-NaringeninChEBI
(2S)-NaringeninChEBI
(S)-2,3-Dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
4',5,7-TrihydroxyflavanoneChEBI
NaringetolChEBI
PelargidanonChEBI
SalipurpolChEBI
(-)-NaringeninHMDB
AsahinaHMDB
NaringenineHMDB
SalipurolHMDB
(2S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneHMDB
(2S)-4',5,7-TrihydroxyflavanoneHMDB
(2S)-4’,5,7-trihydroxyflavanoneHMDB
(S)-NaringeninHMDB
S-DihydrogenisteinHMDB
5,7,4'-TrihydroxyflavanoneHMDB
5,7,4’-trihydroxyflavanoneHMDB
Chemical FormulaC15H12O5
Average Mass272.2528 Da
Monoisotopic Mass272.06847 Da
IUPAC Name(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namenaringenin
CAS Registry Number480-41-1
SMILES
[H][C@]1(CC(=O)C2=C(O1)C=C(O)C=C2O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1
InChI KeyFTVWIRXFELQLPI-ZDUSSCGKSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Abelmoschus esculentusFooDB
Acacia dealbataKNApSAcK Database
Acacia longifoliaKNApSAcK Database
Acer pictum subsp. MonoLOTUS Database
Achyrocline flaccidaLOTUS Database
Acritopappus confertusLOTUS Database
Actinidia chinensisFooDB
Adenothamnus validusLOTUS Database
Aeonium lindleyiLOTUS Database
Aeschynanthus bracteatusKNApSAcK Database
Afzelia bipindensisLOTUS Database
Agaricus bisporusFooDB
AgaveFooDB
Aglaia rubiginosaLOTUS Database
Allagopappus viscosissimusLOTUS Database
Allium ampeloprasumFooDB
Allium ascalonicumFooDB
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosumFooDB
Allium sativumKNApSAcK Database
Allium schoenoprasumFooDB
Allium tuberosumFooDB
Aloysia triphyllaFooDB
Alpinia zerumbetLOTUS Database
AmaranthusFooDB
Ambrosia bidentataLOTUS Database
Amelanchier alnifoliaFooDB
Anacardium occidentaleKNApSAcK Database
Ananas comosusFooDB
Anastatica hierochunticaLOTUS Database
Anethum graveolensFooDB
Angelica keiskeiFooDB
Annona cherimolaFooDB
Annona muricataFooDB
Annona reticulataFooDB
Annona squamosaFooDB
Anthriscus cerefoliumFooDB
Antiphiona pinnatisectaLOTUS Database
Antirrhinum majusKNApSAcK Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceumFooDB
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappaFooDB
Armoracia rusticanaFooDB
Artemisia argyiLOTUS Database
Artemisia barrelieriLOTUS Database
Artemisia campestrisLOTUS Database
Artemisia campestris ssp.maritimaKNApSAcK Database
Artemisia dracunculusFooDB
Artemisia glutinosaKNApSAcK Database
Artemisia spp.KNApSAcK Database
Artemisia vulgarisFooDB
Artocarpus altilisFooDB
Artocarpus heterophyllusFooDB
Asparagus officinalisKNApSAcK Database
Aster koraiensisLOTUS Database
Attalea speciosaFooDB
Auricularia auricula-judaeFooDB
Auricularia polytrichaFooDB
Avena sativaLOTUS Database
Avena sativa L.FooDB
Averrhoa carambolaFooDB
Baccharis dracunculifoliaLOTUS Database
Baccharis linearifoliaLOTUS Database
Baccharis spp.KNApSAcK Database
Bahiopsis laciniataLOTUS Database
Basella albaFooDB
Bauhinia guianensisKNApSAcK Database
Benincasa hispidaFooDB
Berchemia formosanaLOTUS Database
Berchemia racemosaLOTUS Database
Bertholletia excelsaFooDB
Beta vulgarisFooDB
Beta vulgaris ssp. ciclaFooDB
Betula maximowiczianaLOTUS Database
Betula pubescensLOTUS Database
Borago officinalisFooDB
Bracteantha viscosaLOTUS Database
Brassica alboglabraFooDB
Brassica junceaFooDB
Brassica napusFooDB
Brassica napus var. napusFooDB
Brassica oleraceaKNApSAcK Database
Brassica oleracea var. botrytisFooDB
Brassica oleracea var. capitataFooDB
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodesFooDB
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridisFooDB
Brassica rapaFooDB
Brassica rapa ssp. chinensisFooDB
Brassica rapa var. pekinensisFooDB
Brassica rapa var. rapaFooDB
Brassica ruvoFooDB
Brosimum acutifoliumLOTUS Database
Brosimum alicastrumFooDB
Broussonetia papyriferaKNApSAcK Database
Brucea javanicaLOTUS Database
Byrsonima crassifoliaFooDB
Cajanus cajanFooDB
Camellia sinensisLOTUS Database
Camellia sinensis var.assamicaKNApSAcK Database
Canarium ovatumFooDB
Cannabis indicaKNApSAcK Database
Cannabis inflorescencesKNApSAcK Database
Cannabis sativaKNApSAcK Database
Cantharellus cibariusFooDB
Capparis spinosaFooDB
Capsicum annuumKNApSAcK Database
Capsicum annuum L.FooDB
Capsicum annuum var. annuumFooDB
Capsicum chinenseFooDB
Capsicum pubescensFooDB
Carapa guianensisLOTUS Database
Carduus tenuiflorusLOTUS Database
Carica papayaKNApSAcK Database
Carica papaya L.FooDB
Carissa macrocarpaFooDB
Carthamus tinctoriusFooDB
Carum carviFooDB
CaryaFooDB
Carya illinoinensisFooDB
CastaneaFooDB
Castanea crenataFooDB
Castanea mollissimaFooDB
Castanea sativaFooDB
Cedrus deodaraLOTUS Database
Centaurea cyanusLOTUS Database
Centaurea spp.KNApSAcK Database
Ceratonia siliquaFooDB
Chamaemelum nobileFooDB
Chamerion angustifoliumFooDB
Chenopodium albumFooDB
Chenopodium quinoaFooDB
Chrysanthemum coronariumFooDB
Chrysanthemum morifoliumLOTUS Database
Chrysothamnus humilisKNApSAcK Database
Chrysothamnus viscidiflorusKNApSAcK Database
Cicer arietinumFooDB
Cichorium endiviaFooDB
Cichorium intybusFooDB
CinnamomumFooDB
Cinnamomum aromaticumFooDB
Cinnamomum verumFooDB
CirsiumFooDB
Cistus laurifoliusLOTUS Database
Citrullus lanatusFooDB
Citrus ×limon (L.) Burm. f. (pro sp.)FooDB
Citrus aurantiifoliaFooDB
Citrus aurantiumLOTUS Database
Citrus aurantium L. var. amaraKNApSAcK Database
Citrus grandisKNApSAcK Database
Citrus grandis var.tomentosaKNApSAcK Database
Citrus latifoliaFooDB
Citrus limonFooDB
Citrus maximaFooDB
Citrus medicaLOTUS Database
Citrus paradisiFooDB
Citrus reticulataFooDB
Citrus sinensisLOTUS Database
Citrus spp.KNApSAcK Database
Citrus trifoliataLOTUS Database
Citrus unshiuKNApSAcK Database
Citrus X sinensis (L.) Osbeck (pro. sp.)FooDB
Cochlospermum gillivraeiKNApSAcK Database
Cocos nuciferaFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Colocasia esculentaFooDB
Combretum imberbeLOTUS Database
Commiphora wightiiLOTUS Database
Corchorus olitoriusFooDB
Coriandrum sativum L.FooDB
Coriaria intermediaLOTUS Database
CorylusFooDB
Corylus avellanaFooDB
Corymbia maculataLOTUS Database
Cota palaestinaLOTUS Database
Cotoneaster orbicularisLOTUS Database
Couepia paraensisLOTUS Database
Craspedolobium schochiiLOTUS Database
Crateva religiosaFooDB
Crocus sativusFooDB
Crotalaria assamicaKNApSAcK Database
Crotalaria pallidaKNApSAcK Database
Cryptomeria japonicaLOTUS Database
Cucumis meloFooDB
Cucumis metuliferusFooDB
Cucumis sativus L.FooDB
CucurbitaFooDB
Cucurbita maximaFooDB
Cucurbita moschataFooDB
Cudrania cochinchinensis var. gerontogeaKNApSAcK Database
Cuminum cyminumFooDB
Curcuma longaFooDB
Curcuma manggaKNApSAcK Database
Cycas circinalisLOTUS Database
Cyclopia intermediaLOTUS Database
Cydonia oblongaFooDB
Cymbopogon citratusFooDB
Cynara cardunculusFooDB
Cynara scolymusFooDB
Dahlia spp.KNApSAcK Database
Dalbergia odoriferaKNApSAcK Database
Dalbergia parvifloraLOTUS Database
Dalbergia stevensoniiKNApSAcK Database
Daucus carotaKNApSAcK Database
Daucus carota ssp. sativusFooDB
Deinandra minthorniiLOTUS Database
Dendrobium densiflorumLOTUS Database
Dendrobium densiflorum Lindl.ex.Wall.KNApSAcK Database
Dimocarpus longanFooDB
DioscoreaFooDB
Dioscorea alataKNApSAcK Database
Dioscorea pentaphyllaFooDB
DiospyrosFooDB
Diospyros kakiFooDB
Diospyros virginianaFooDB
Diplostephium cinereumLOTUS Database
Dracocephalum tanguticumLOTUS Database
Durio zibethinusFooDB
Dysphania ambrosioidesFooDB
ElaeisFooDB
Elaeodendron croceumLOTUS Database
Eleocharis dulcisFooDB
Elettaria cardamomumFooDB
Empetrum nigrumFooDB
Entada phaseoloidesLOTUS Database
Ephedra sinicaKNApSAcK Database
Equisetum arvenseLOTUS Database
Eragrostis tefFooDB
Eriobotrya japonicaFooDB
Eriodictyon angustifoliumLOTUS Database
Eruca vesicaria subsp. SativaFooDB
Euchresta japonicaLOTUS Database
Eugenia javanicaFooDB
Eugenia unifloraFooDB
Euphorbia helioscopiaPlant
Euscaphis konishiiKNApSAcK Database
Eutrema japonicumFooDB
Fagopyrum esculentumFooDB
Fagopyrum tataricumFooDB
FagusFooDB
Feijoa sellowianaFooDB
Ficus caricaFooDB
Ficus nervosaLOTUS Database
Ficus pumilaLOTUS Database
Flammulina velutipesFooDB
Flemingia philippinensisLOTUS Database
Flemingia strictaKNApSAcK Database
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Garcinia mangostanaFooDB
Garcinia multifloraKNApSAcK Database
Garcinia neglectaKNApSAcK Database
Gaylussacia baccataFooDB
Gentiana lutea L. var. aurantiacaKNApSAcK Database
Gentiana trifloraKNApSAcK Database
Ginkgo bilobaKNApSAcK Database
Glycine maxKNApSAcK Database
Glycyrrhiza echinataLOTUS Database
Glycyrrhiza glabraKNApSAcK Database
Glycyrrhiza uralensisKNApSAcK Database
GossypiumFooDB
Goyazianthus tetrastichusLOTUS Database
Grifola frondosaFooDB
Gynerium sagittatumKNApSAcK Database
Hedysarum alpinumFooDB
Helianthus annuus L.FooDB
Helianthus tuberosusFooDB
Helichrysum arenariumKNApSAcK Database
Helichrysum armeniumLOTUS Database
Helichrysum bracteatum (Vent.)Andr.KNApSAcK Database
Helichrysum graveolenKNApSAcK Database
Heliotropium chenopodiaceumLOTUS Database
Heliotropium sclerocarpumLOTUS Database
Heliotropium sinuatumLOTUS Database
Heliotropium taltalenseLOTUS Database
Hibiscus sabbariffaFooDB
Hippophae rhamnoidesFooDB
Hordeum vulgareFooDB
Hymenoclea monogyraLOTUS Database
Hyssopus officinalis L.FooDB
Illicium verumFooDB
Intsia bijugaKNApSAcK Database
Inula salsoloidesLOTUS Database
Inulanthera calvaLOTUS Database
Ipomoea aquaticaFooDB
Ipomoea batatasFooDB
JuglansFooDB
Juglans ailanthifoliaFooDB
Juglans cinereaFooDB
Juglans nigra L.FooDB
Juglans regiaFooDB
Juniperus chinensisLOTUS Database
Lablab purpureusFooDB
Lactuca sativaFooDB
Lagenaria sicerariaFooDB
Laguncularia racemosaLOTUS Database
Lamyropsis cynaroidesLOTUS Database
Lathyrus sativusFooDB
Laurus nobilis L.FooDB
Leiocarpa semicalvaLOTUS Database
Lens culinarisFooDB
Lentinus edodesFooDB
Lepidium sativumFooDB
Lespedeza cyrtobotryaKNApSAcK Database
Levisticum officinaleFooDB
Limonium aureumLOTUS Database
Limonium sinenseLOTUS Database
Linum usitatissimumFooDB
Lippia graveolensLOTUS Database
Lippia origanoidesLOTUS Database
Litchi chinensisFooDB
Lonicera japonicaKNApSAcK Database
Lotus uliginosusLOTUS Database
Luffa aegyptiacaFooDB
LupinusFooDB
Lupinus albusFooDB
Lupinus subcarnosusKNApSAcK Database
Lupinus texensisKNApSAcK Database
Lychnophora ericoidesLOTUS Database
Maackia amurensisLOTUS Database
MacadamiaFooDB
Macadamia tetraphyllaFooDB
Maclura cochinchinensisLOTUS Database
Maclura pomiferaLOTUS Database
Maclura tinctoriaKNApSAcK Database
Maclura tricuspidataLOTUS Database
Magnolia denudataKNApSAcK Database
Magnolia liliifloraKNApSAcK Database
Malpighia emarginataFooDB
MalusFooDB
Malus pumilaFooDB
Mammea americanaFooDB
Mandevilla hirsutaLOTUS Database
Mangifera indicaFooDB
Manihot esculentaFooDB
Manilkara zapotaFooDB
Maranta arundinaceaFooDB
Matricaria chamomillaLOTUS Database
Matricaria recutitaFooDB
Matteuccia struthiopterisFooDB
Matthiola incanaLOTUS Database
Medicago arabicaKNApSAcK Database
Medicago sativaKNApSAcK Database
Medicago truncatulaKNApSAcK Database
Melissa officinalis L.FooDB
MenthaFooDB
Mentha aquaticaFooDB
Mentha arvensisFooDB
Mentha spicataFooDB
Mentha x piperitaFooDB
Mespilus germanicaFooDB
Metroxylon saguFooDB
Millettia brandisianaKNApSAcK Database
Mimosa hostilisKNApSAcK Database
Mimosa tenuifloraLOTUS Database
Momordica charantiaKNApSAcK Database
Monopteryx inpaeLOTUS Database
MorchellaceaeFooDB
Morella rubraFooDB
Moringa oleiferaFooDB
MorusFooDB
Morus nigraFooDB
Musa acuminataKNApSAcK Database
Musa x paradisiacaFooDB
MyricaFooDB
Myristica fragransFooDB
NelumboFooDB
Nelumbo nuciferaFooDB
Nephelium lappaceumFooDB
Nuphar luteaFooDB
Nymphaea caeruleaKNApSAcK Database
Ocimum basilicumFooDB
Oenothera biennisFooDB
Olea europaeaFooDB
OpuntiaFooDB
Opuntia cochenilliferaFooDB
Opuntia macrorhizaFooDB
Origanum dictamnusLOTUS Database
Origanum majoranaFooDB
Origanum onitesFooDB
Origanum vulgareFooDB
Origanum X majoricumFooDB
Ormosia henryiLOTUS Database
Ormosia monospermaLOTUS Database
Oryza rufipogonFooDB
Oryza sativaKNApSAcK Database
Pachyrhizus erosusFooDB
Panax ginsengFooDB
Pangium eduleFooDB
Panicum miliaceumFooDB
Passiflora edulisFooDB
Pastinaca sativaFooDB
Paulownia coreanaLOTUS Database
Paulownia tomentosaLOTUS Database
Pediomelum esculentumFooDB
Perideridia oreganaFooDB
Persea americanaFooDB
Petasites japonicusFooDB
Petroselinum crispumFooDB
Petunia hybridaKNApSAcK Database
Phaseolus coccineusFooDB
Phaseolus lunatusFooDB
Phaseolus vulgarisFooDB
Phlomis aureaLOTUS Database
Phlomis caucasicaKNApSAcK Database
Phoenix dactyliferaFooDB
Photinia melanocarpaFooDB
Phyllanthus emblicaKNApSAcK Database
Phyllostachys edulisFooDB
PhysalisFooDB
Physalis philadelphica var. immaculataFooDB
Phytolacca americanaFooDB
Picea jezoensisLOTUS Database
Pimenta dioicaFooDB
Pimpinella anisumFooDB
PinusFooDB
Pinus edulisFooDB
Pinus sibiricaKNApSAcK Database
Piper crassinerviumLOTUS Database
Piper crassinervium KunthKNApSAcK Database
Piper nigrum L.FooDB
Pistacia veraFooDB
Pisum sativumFooDB
Pittocaulon praecoxLOTUS Database
Pittocaulon velatumLOTUS Database
Plazia daphnoidesLOTUS Database
Pleurotus ostreatusFooDB
Podocarpus fasciculusKNApSAcK Database
Polygonum alpinumFooDB
Polygonum minusKNApSAcK Database
Polymnia fruticosaKNApSAcK Database
Populus balsamiferaLOTUS Database
Populus davidianaLOTUS Database
Populus deltoidesLOTUS Database
Populus szechuanicaLOTUS Database
Populus tremulaLOTUS Database
Populus tremuloidesLOTUS Database
Portulaca oleraceaFooDB
Pouteria sapotaFooDB
Premna fulvaLOTUS Database
Prunus armeniacaFooDB
Prunus aviumKNApSAcK Database
Prunus avium L.FooDB
Prunus campanulataLOTUS Database
Prunus cerasusKNApSAcK Database
Prunus cornutaLOTUS Database
Prunus davidianaKNApSAcK Database
Prunus domesticaFooDB
Prunus dulcisFooDB
Prunus mumeKNApSAcK Database
Prunus persicaKNApSAcK Database
Prunus persica var. nucipersicaFooDB
Prunus persica var. persicaFooDB
Prunus serrulataLOTUS Database
Prunus tomentosaFooDB
Prunus virginianaFooDB
Prunus yedoensisKNApSAcK Database
Pseudotsuga wilsonianaKNApSAcK Database
Psidium cattleianumFooDB
Psidium guajavaFooDB
Psophocarpus tetragonolobusFooDB
Pterocarpus marsupiumKNApSAcK Database
Punica granatumFooDB
Punica granatum L.KNApSAcK Database
Pyracantha coccineaLOTUS Database
Pyrus communisFooDB
Pyrus pyrifoliaFooDB
QuercusFooDB
Raphanus sativusKNApSAcK Database
Raphanus sativus var. longipinnatusFooDB
Raphanus sativus var. sativusFooDB
Retama raetamLOTUS Database
Rheum rhabarbarumFooDB
Rhynchosia beddomeiKNApSAcK Database
Ribes aureumFooDB
Ribes glandulosumFooDB
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispaFooDB
RosaFooDB
Rubus arcticusFooDB
Rubus chamaemorusFooDB
Rubus idaeusFooDB
Rubus occidentalisFooDB
Rubus spectabilisFooDB
RumexFooDB
Rumex acetosaFooDB
Rumex articusFooDB
Sagittaria latifoliaFooDB
Salix capreaLOTUS Database
Salix pulchraFooDB
Salvia elegansFooDB
Salvia hispanicaFooDB
Salvia mexicanaLOTUS Database
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Salvia xalapensisLOTUS Database
Sambucus nigraFooDB
Sambucus nigra L.FooDB
Sarcophyte sanguineaLOTUS Database
Satureja cuneifoliaLOTUS Database
Satureja hortensis L.FooDB
Satureja montanaFooDB
Satureja subspicataKNApSAcK Database
Scalesia bauriiLOTUS Database
Scorzonera hispanicaFooDB
Scutellaria strigillosaLOTUS Database
Secale cerealeFooDB
Sechium eduleFooDB
Senna toraLOTUS Database
Sesamum indicumFooDB
Sesbania bispinosaFooDB
Shuteria involucrataLOTUS Database
Sinapis albaFooDB
Sinningia cardinalisLOTUS Database
SisymbriumFooDB
Smallanthus fruticosusLOTUS Database
Smilax bracteataPlant
Smilax corbulariaLOTUS Database
Smilax excelsaLOTUS Database
Smilax perfoliataLOTUS Database
Solanum lycopersicumFooDB
Solanum lycopersicum var. cerasiformeFooDB
Solanum lycopersicum var. lycopersicumFooDB
Solanum melongenaFooDB
Solanum quitoenseFooDB
Solanum tuberosumFooDB
Sophora flavescensKNApSAcK Database
Sophora japonicaKNApSAcK Database
Sorbus aucupariaFooDB
Sorghum bicolorFooDB
Spinacia oleraceaFooDB
Stachys aegyptiacaLOTUS Database
Steiractinia sodiroiLOTUS Database
Streptomyces graminofaciensLOTUS Database
Swartzia polyphyllaKNApSAcK Database
Syzygium aromaticumFooDB
Syzygium cuminiFooDB
Syzygium jambosFooDB
Tamarindus indicaFooDB
Taraxacum officinaleFooDB
Taxus chinensisKNApSAcK Database
Taxus fuanaKNApSAcK Database
Taxus wallichianaLOTUS Database
Taxus yunnanensisKNApSAcK Database
Tetragonia tetragonioidesFooDB
Teucrium chamaedrysLOTUS Database
ThelespermaFooDB
Theobroma cacao L.KNApSAcK Database
Thymus herba-baronaLOTUS Database
Thymus pulegioidesFooDB
Thymus vulgarisFooDB
Tilia cordataFooDB
Tilia L.FooDB
Tragopogon porrifoliusFooDB
Trigonella foenum-graecumKNApSAcK Database
TriticumFooDB
Triticum aestivumFooDB
Triticum durumFooDB
Triticum speltaFooDB
Triticum turanicumFooDB
Typha angustifoliaKNApSAcK Database
Urospermum dalechampiiLOTUS Database
VacciniumFooDB
Vaccinium angustifoliumFooDB
Vaccinium angustifolium X Vaccinium corymbosumFooDB
Vaccinium arboreumFooDB
Vaccinium corymbosumFooDB
Vaccinium deliciosumFooDB
Vaccinium elliottiiFooDB
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Vachellia niloticaLOTUS Database
Valerianella locustaFooDB
VanillaFooDB
Verbena officinalisFooDB
Viburnum cotinifoliumLOTUS Database
Viburnum eduleFooDB
Vicia fabaKNApSAcK Database
Vigna aconitifoliaFooDB
Vigna angularisFooDB
Vigna mungoFooDB
Vigna radiataFooDB
Vigna umbellataFooDB
Vigna unguiculataFooDB
Vigna unguiculata ssp. cylindricaFooDB
Vigna unguiculata ssp. unguiculataFooDB
Vigna unguiculata var. sesquipedalisFooDB
Viscum angulatumKNApSAcK Database
Viscum coloratumKNApSAcK Database
VitisFooDB
Vitis aestivalisFooDB
Vitis labruscaFooDB
Vitis rotundifoliaFooDB
Vitis viniferaLOTUS Database
Vitis vinifera L.FooDB
Wyethia angustifoliaLOTUS Database
Xanthoceras sorbifoliaKNApSAcK Database
Xanthoceras sorbifoliumLOTUS Database
Xanthorrhoea fulvaLOTUS Database
Xanthosoma sagittifoliumFooDB
Xerochrysum bracteatumLOTUS Database
Xylopia poilaneiKNApSAcK Database
Zea maysKNApSAcK Database
Zea mays L.FooDB
Zingiber officinaleFooDB
ZizaniaFooDB
Zizania aquaticaFooDB
Ziziphus zizyphusFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanones
Alternative Parents
Substituents
  • Flavanone
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point251 °CNot Available
Boiling Point577.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility475.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.52Perrissoud, D., & Testa, B. (1986). Inhibiting or potentiating effects of flavonoids on carbon tetrachloride-induced toxicity in isolated rat hepatocytes. Arzneimittel-forschung, 36(8), 1249-1253.
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP2.47ALOGPS
logP2.84ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.86ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.29 m³·mol⁻¹ChemAxon
Polarizability27.31 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002670
DrugBank IDDB03467
Phenol Explorer Compound ID201
FoodDB IDFDB000678
KNApSAcK IDC00000982
Chemspider ID388383
KEGG Compound IDC00509
BioCyc IDNARINGENIN-CMPD
BiGG IDNot Available
Wikipedia LinkNaringenin
METLIN ID3401
PubChem Compound439246
PDB IDNot Available
ChEBI ID17846
Good Scents IDrw1193531
References
General References
  1. Miniscalco A, Lundahl J, Regardh CG, Edgar B, Eriksson UG: Inhibition of dihydropyridine metabolism in rat and human liver microsomes by flavonoids found in grapefruit juice. J Pharmacol Exp Ther. 1992 Jun;261(3):1195-9. [PubMed:1602384 ]
  2. Walker D, Flinois JP, Monkman SC, Beloc C, Boddy AV, Cholerton S, Daly AK, Lind MJ, Pearson AD, Beaune PH, et al.: Identification of the major human hepatic cytochrome P450 involved in activation and N-dechloroethylation of ifosfamide. Biochem Pharmacol. 1994 Mar 29;47(7):1157-63. [PubMed:8161344 ]
  3. Ameer B, Weintraub RA, Johnson JV, Yost RA, Rouseff RL: Flavanone absorption after naringin, hesperidin, and citrus administration. Clin Pharmacol Ther. 1996 Jul;60(1):34-40. [PubMed:8689809 ]
  4. Kanaze FI, Kokkalou E, Georgarakis M, Niopas I: Validated high-performance liquid chromatographic method utilizing solid-phase extraction for the simultaneous determination of naringenin and hesperetin in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Mar 5;801(2):363-7. [PubMed:14751808 ]
  5. Guengerich FP, Kim DH: In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis. 1990 Dec;11(12):2275-9. [PubMed:2265479 ]
  6. Ishii K, Furuta T, Kasuya Y: Determination of naringin and naringenin in human plasma by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Aug 30;683(2):225-9. [PubMed:8891919 ]
  7. Matsuo M, Sasaki N, Saga K, Kaneko T: Cytotoxicity of flavonoids toward cultured normal human cells. Biol Pharm Bull. 2005 Feb;28(2):253-9. [PubMed:15684479 ]
  8. Franke AA, Cooney RV, Henning SM, Custer LJ: Bioavailability and antioxidant effects of orange juice components in humans. J Agric Food Chem. 2005 Jun 29;53(13):5170-8. [PubMed:15969493 ]
  9. Fuhr U, Kummert AL: The fate of naringin in humans: a key to grapefruit juice-drug interactions? Clin Pharmacol Ther. 1995 Oct;58(4):365-73. [PubMed:7586927 ]
  10. Lin YT, Hsiu SL, Hou YC, Chen HY, Chao PD: Degradation of flavonoid aglycones by rabbit, rat and human fecal flora. Biol Pharm Bull. 2003 May;26(5):747-51. [PubMed:12736527 ]
  11. Malaveille C, Hautefeuille A, Pignatelli B, Talaska G, Vineis P, Bartsch H: Dietary phenolics as anti-mutagens and inhibitors of tobacco-related DNA adduction in the urothelium of smokers. Carcinogenesis. 1996 Oct;17(10):2193-200. [PubMed:8895488 ]