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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 esculentus
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 bisporus
Agave
Aglaia rubiginosaLOTUS Database
Allagopappus viscosissimusLOTUS Database
Allium ampeloprasum
Allium ascalonicum
Allium cepaFooDB
Allium cepa L.FooDB
Allium fistulosum
Allium sativumKNApSAcK Database
Allium schoenoprasum
Allium tuberosum
Aloysia triphylla
Alpinia zerumbetLOTUS Database
Amaranthus
Ambrosia bidentataLOTUS Database
Amelanchier alnifolia
Anacardium occidentaleKNApSAcK Database
Ananas comosusFooDB
Anastatica hierochunticaLOTUS Database
Anethum graveolensFooDB
Angelica keiskei
Annona cherimola
Annona muricata
Annona reticulata
Annona squamosa
Anthriscus cerefolium
Antiphiona pinnatisectaLOTUS Database
Antirrhinum majusKNApSAcK Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
Apium graveolens var. rapaceum
Apium graveolens var. secalinumFooDB
Arabidopsis thalianaKNApSAcK Database
Arachis hypogaeaFooDB
Arctium lappa
Armoracia rusticana
Artemisia argyiLOTUS Database
Artemisia barrelieriLOTUS Database
Artemisia campestrisLOTUS Database
Artemisia campestris ssp.maritimaKNApSAcK Database
Artemisia dracunculusFooDB
Artemisia glutinosaKNApSAcK Database
Artemisia spp.KNApSAcK Database
Artemisia vulgaris
Artocarpus altilis
Artocarpus heterophyllus
Asparagus officinalisKNApSAcK Database
Aster koraiensisLOTUS Database
Attalea speciosa
Auricularia auricula-judae
Auricularia polytricha
Avena sativaLOTUS Database
Avena sativa L.
Averrhoa carambola
Baccharis dracunculifoliaLOTUS Database
Baccharis linearifoliaLOTUS Database
Baccharis spp.KNApSAcK Database
Bahiopsis laciniataLOTUS Database
Basella alba
Bauhinia guianensisKNApSAcK Database
Benincasa hispida
Berchemia formosanaLOTUS Database
Berchemia racemosaLOTUS Database
Bertholletia excelsaFooDB
Beta vulgaris
Beta vulgaris ssp. cicla
Betula maximowiczianaLOTUS Database
Betula pubescensLOTUS Database
Borago officinalis
Bracteantha viscosaLOTUS Database
Brassica alboglabra
Brassica juncea
Brassica napus
Brassica napus var. napus
Brassica oleraceaKNApSAcK Database
Brassica oleracea var. botrytis
Brassica oleracea var. capitata
Brassica oleracea var. gemmiferaFooDB
Brassica oleracea var. gongylodes
Brassica oleracea var. italicaFooDB
Brassica oleracea var. sabaudaFooDB
Brassica oleracea var. viridis
Brassica rapa
Brassica rapa ssp. chinensis
Brassica rapa var. pekinensis
Brassica rapa var. rapa
Brassica ruvoFooDB
Brosimum acutifoliumLOTUS Database
Brosimum alicastrum
Broussonetia papyriferaKNApSAcK Database
Brucea javanicaLOTUS Database
Byrsonima crassifolia
Cajanus cajan
Camellia sinensisLOTUS Database
Camellia sinensis var.assamicaKNApSAcK Database
Canarium ovatum
Cannabis indicaKNApSAcK Database
Cannabis inflorescencesKNApSAcK Database
Cannabis sativaKNApSAcK Database
Cantharellus cibarius
Capparis spinosa
Capsicum annuumKNApSAcK Database
Capsicum annuum L.
Capsicum annuum var. annuum
Capsicum chinense
Capsicum pubescens
Carapa guianensisLOTUS Database
Carduus tenuiflorusLOTUS Database
Carica papayaKNApSAcK Database
Carica papaya L.
Carissa macrocarpa
Carthamus tinctorius
Carum carvi
Carya
Carya illinoinensisFooDB
Castanea
Castanea crenata
Castanea mollissima
Castanea sativa
Cedrus deodaraLOTUS Database
Centaurea cyanusLOTUS Database
Centaurea spp.KNApSAcK Database
Ceratonia siliqua
Chamaemelum nobile
Chamerion angustifolium
Chenopodium album
Chenopodium quinoa
Chrysanthemum coronarium
Chrysanthemum morifoliumLOTUS Database
Chrysothamnus humilisKNApSAcK Database
Chrysothamnus viscidiflorusKNApSAcK Database
Cicer arietinum
Cichorium endivia
Cichorium intybus
Cinnamomum
Cinnamomum aromaticum
Cinnamomum verum
Cirsium
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 nucifera
Coffea arabica L.
Coffea canephora
Colocasia esculenta
Combretum imberbeLOTUS Database
Commiphora wightiiLOTUS Database
Corchorus olitorius
Coriandrum sativum L.FooDB
Coriaria intermediaLOTUS Database
CorylusFooDB
Corylus avellana
Corymbia maculataLOTUS Database
Cota palaestinaLOTUS Database
Cotoneaster orbicularisLOTUS Database
Couepia paraensisLOTUS Database
Craspedolobium schochiiLOTUS Database
Crateva religiosa
Crocus sativus
Crotalaria assamicaKNApSAcK Database
Crotalaria pallidaKNApSAcK Database
Cryptomeria japonicaLOTUS Database
Cucumis meloFooDB
Cucumis metuliferus
Cucumis sativus L.
Cucurbita
Cucurbita maxima
Cucurbita moschata
Cudrania cochinchinensis var. gerontogeaKNApSAcK Database
Cuminum cyminumFooDB
Curcuma longa
Curcuma manggaKNApSAcK Database
Cycas circinalisLOTUS Database
Cyclopia intermediaLOTUS Database
Cydonia oblonga
Cymbopogon citratus
Cynara cardunculus
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 longan
Dioscorea
Dioscorea alataKNApSAcK Database
Dioscorea pentaphylla
Diospyros
Diospyros kaki
Diospyros virginiana
Diplostephium cinereumLOTUS Database
Dracocephalum tanguticumLOTUS Database
Durio zibethinus
Dysphania ambrosioides
Elaeis
Elaeodendron croceumLOTUS Database
Eleocharis dulcis
Elettaria cardamomum
Empetrum nigrum
Entada phaseoloidesLOTUS Database
Ephedra sinicaKNApSAcK Database
Equisetum arvenseLOTUS Database
Eragrostis tef
Eriobotrya japonica
Eriodictyon angustifoliumLOTUS Database
Eruca vesicaria subsp. Sativa
Euchresta japonicaLOTUS Database
Eugenia javanica
Eugenia uniflora
Euphorbia helioscopiaPlant
Euscaphis konishiiKNApSAcK Database
Eutrema japonicum
Fagopyrum esculentum
Fagopyrum tataricum
Fagus
Feijoa sellowiana
Ficus caricaFooDB
Ficus nervosaLOTUS Database
Ficus pumilaLOTUS Database
Flammulina velutipes
Flemingia philippinensisLOTUS Database
Flemingia strictaKNApSAcK Database
Foeniculum vulgareFooDB
Fragaria x ananassaFooDB
Garcinia mangostana
Garcinia multifloraKNApSAcK Database
Garcinia neglectaKNApSAcK Database
Gaylussacia baccata
Gentiana lutea L. var. aurantiacaKNApSAcK Database
Gentiana trifloraKNApSAcK Database
Ginkgo bilobaKNApSAcK Database
Glycine maxKNApSAcK Database
Glycyrrhiza echinataLOTUS Database
Glycyrrhiza glabraKNApSAcK Database
Glycyrrhiza uralensisKNApSAcK Database
Gossypium
Goyazianthus tetrastichusLOTUS Database
Grifola frondosa
Gynerium sagittatumKNApSAcK Database
Hedysarum alpinum
Helianthus annuus L.
Helianthus tuberosus
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 sabbariffa
Hippophae rhamnoides
Hordeum vulgare
Hymenoclea monogyraLOTUS Database
Hyssopus officinalis L.FooDB
Illicium verum
Intsia bijugaKNApSAcK Database
Inula salsoloidesLOTUS Database
Inulanthera calvaLOTUS Database
Ipomoea aquatica
Ipomoea batatas
Juglans
Juglans ailanthifolia
Juglans cinerea
Juglans nigra L.
Juglans regiaFooDB
Juniperus chinensisLOTUS Database
Lablab purpureus
Lactuca sativaFooDB
Lagenaria siceraria
Laguncularia racemosaLOTUS Database
Lamyropsis cynaroidesLOTUS Database
Lathyrus sativus
Laurus nobilis L.
Leiocarpa semicalvaLOTUS Database
Lens culinaris
Lentinus edodes
Lepidium sativum
Lespedeza cyrtobotryaKNApSAcK Database
Levisticum officinale
Limonium aureumLOTUS Database
Limonium sinenseLOTUS Database
Linum usitatissimum
Lippia graveolensLOTUS Database
Lippia origanoidesLOTUS Database
Litchi chinensis
Lonicera japonicaKNApSAcK Database
Lotus uliginosusLOTUS Database
Luffa aegyptiaca
Lupinus
Lupinus albus
Lupinus subcarnosusKNApSAcK Database
Lupinus texensisKNApSAcK Database
Lychnophora ericoidesLOTUS Database
Maackia amurensisLOTUS Database
MacadamiaFooDB
Macadamia tetraphylla
Maclura cochinchinensisLOTUS Database
Maclura pomiferaLOTUS Database
Maclura tinctoriaKNApSAcK Database
Maclura tricuspidataLOTUS Database
Magnolia denudataKNApSAcK Database
Magnolia liliifloraKNApSAcK Database
Malpighia emarginata
Malus
Malus pumilaFooDB
Mammea americana
Mandevilla hirsutaLOTUS Database
Mangifera indica
Manihot esculenta
Manilkara zapota
Maranta arundinacea
Matricaria chamomillaLOTUS Database
Matricaria recutitaFooDB
Matteuccia struthiopteris
Matthiola incanaLOTUS Database
Medicago arabicaKNApSAcK Database
Medicago sativaKNApSAcK Database
Medicago truncatulaKNApSAcK Database
Melissa officinalis L.FooDB
Mentha
Mentha aquatica
Mentha arvensis
Mentha spicataFooDB
Mentha x piperita
Mespilus germanica
Metroxylon sagu
Millettia brandisianaKNApSAcK Database
Mimosa hostilisKNApSAcK Database
Mimosa tenuifloraLOTUS Database
Momordica charantiaKNApSAcK Database
Monopteryx inpaeLOTUS Database
Morchellaceae
Morella rubra
Moringa oleifera
Morus
Morus nigra
Musa acuminataKNApSAcK Database
Musa x paradisiaca
Myrica
Myristica fragrans
Nelumbo
Nelumbo nucifera
Nephelium lappaceum
Nuphar lutea
Nymphaea caeruleaKNApSAcK Database
Ocimum basilicumFooDB
Oenothera biennis
Olea europaea
Opuntia
Opuntia cochenillifera
Opuntia macrorhiza
Origanum dictamnusLOTUS Database
Origanum majoranaFooDB
Origanum onites
Origanum vulgareFooDB
Origanum X majoricum
Ormosia henryiLOTUS Database
Ormosia monospermaLOTUS Database
Oryza rufipogon
Oryza sativaKNApSAcK Database
Pachyrhizus erosus
Panax ginseng
Pangium edule
Panicum miliaceum
Passiflora edulis
Pastinaca sativa
Paulownia coreanaLOTUS Database
Paulownia tomentosaLOTUS Database
Pediomelum esculentum
Perideridia oregana
Persea americanaFooDB
Petasites japonicus
Petroselinum crispumFooDB
Petunia hybridaKNApSAcK Database
Phaseolus coccineus
Phaseolus lunatus
Phaseolus vulgarisFooDB
Phlomis aureaLOTUS Database
Phlomis caucasicaKNApSAcK Database
Phoenix dactyliferaFooDB
Photinia melanocarpa
Phyllanthus emblicaKNApSAcK Database
Phyllostachys edulis
Physalis
Physalis philadelphica var. immaculata
Phytolacca americana
Picea jezoensisLOTUS Database
Pimenta dioica
Pimpinella anisumFooDB
Pinus
Pinus edulisFooDB
Pinus sibiricaKNApSAcK Database
Piper crassinerviumLOTUS Database
Piper crassinervium KunthKNApSAcK Database
Piper nigrum L.
Pistacia veraFooDB
Pisum sativum
Pittocaulon praecoxLOTUS Database
Pittocaulon velatumLOTUS Database
Plazia daphnoidesLOTUS Database
Pleurotus ostreatus
Podocarpus fasciculusKNApSAcK Database
Polygonum alpinum
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 oleracea
Pouteria sapota
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. persica
Prunus serrulataLOTUS Database
Prunus tomentosa
Prunus virginiana
Prunus yedoensisKNApSAcK Database
Pseudotsuga wilsonianaKNApSAcK Database
Psidium cattleianum
Psidium guajava
Psophocarpus tetragonolobus
Pterocarpus marsupiumKNApSAcK Database
Punica granatum
Punica granatum L.KNApSAcK Database
Pyracantha coccineaLOTUS Database
Pyrus communisFooDB
Pyrus pyrifolia
Quercus
Raphanus sativusKNApSAcK Database
Raphanus sativus var. longipinnatus
Raphanus sativus var. sativus
Retama raetamLOTUS Database
Rheum rhabarbarum
Rhynchosia beddomeiKNApSAcK Database
Ribes aureum
Ribes glandulosum
Ribes nigrumFooDB
Ribes rubrumFooDB
Ribes uva-crispa
Rosa
Rubus arcticus
Rubus chamaemorus
Rubus idaeusFooDB
Rubus occidentalis
Rubus spectabilis
Rumex
Rumex acetosa
Rumex articus
Sagittaria latifolia
Salix capreaLOTUS Database
Salix pulchra
Salvia elegans
Salvia hispanica
Salvia mexicanaLOTUS Database
Salvia officinalisFooDB
Salvia rosmarinusFooDB
Salvia xalapensisLOTUS Database
Sambucus nigra
Sambucus nigra L.
Sarcophyte sanguineaLOTUS Database
Satureja cuneifoliaLOTUS Database
Satureja hortensis L.
Satureja montana
Satureja subspicataKNApSAcK Database
Scalesia bauriiLOTUS Database
Scorzonera hispanica
Scutellaria strigillosaLOTUS Database
Secale cereale
Sechium edule
Senna toraLOTUS Database
Sesamum indicum
Sesbania bispinosa
Shuteria involucrataLOTUS Database
Sinapis alba
Sinningia cardinalisLOTUS Database
Sisymbrium
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 melongena
Solanum quitoense
Solanum tuberosumFooDB
Sophora flavescensKNApSAcK Database
Sophora japonicaKNApSAcK Database
Sorbus aucuparia
Sorghum bicolorFooDB
Spinacia oleracea
Stachys aegyptiacaLOTUS Database
Steiractinia sodiroiLOTUS Database
Streptomyces graminofaciensLOTUS Database
Swartzia polyphyllaKNApSAcK Database
Syzygium aromaticum
Syzygium cumini
Syzygium jambos
Tamarindus indica
Taraxacum officinale
Taxus chinensisKNApSAcK Database
Taxus fuanaKNApSAcK Database
Taxus wallichianaLOTUS Database
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Tetragonia tetragonioides
Teucrium chamaedrysLOTUS Database
Thelesperma
Theobroma cacao L.KNApSAcK Database
Thymus herba-baronaLOTUS Database
Thymus pulegioides
Thymus vulgarisFooDB
Tilia cordata
Tilia L.
Tragopogon porrifolius
Trigonella foenum-graecumKNApSAcK Database
Triticum
Triticum aestivum
Triticum durum
Triticum spelta
Triticum turanicum
Typha angustifoliaKNApSAcK Database
Urospermum dalechampiiLOTUS Database
VacciniumFooDB
Vaccinium angustifolium
Vaccinium angustifolium X Vaccinium corymbosum
Vaccinium arboreum
Vaccinium corymbosum
Vaccinium deliciosum
Vaccinium elliottii
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Vaccinium myrtilloides
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Vaccinium ovalifolium
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Vaccinium uliginosum
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Vachellia niloticaLOTUS Database
Valerianella locusta
Vanilla
Verbena officinalis
Viburnum cotinifoliumLOTUS Database
Viburnum edule
Vicia fabaKNApSAcK Database
Vigna aconitifolia
Vigna angularis
Vigna mungo
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Vigna umbellata
Vigna unguiculata
Vigna unguiculata ssp. cylindrica
Vigna unguiculata ssp. unguiculata
Vigna unguiculata var. sesquipedalis
Viscum angulatumKNApSAcK Database
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Vitis
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Xerochrysum bracteatumLOTUS Database
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Zea maysKNApSAcK Database
Zea mays L.
Zingiber officinale
Zizania
Zizania aquatica
Ziziphus zizyphus
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 ]