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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:20 UTC
Update Date2020-02-26 21:24:19 UTC
HMDB IDHMDB0002927
Secondary Accession Numbers
  • HMDB02927
Metabolite Identification
Common NameNaringin
DescriptionNaringin, also known as naringoside or naringin hydrate, 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. It is metabolized to the flavonone naringenin in humans. Naringin is an extremely weak basic (essentially neutral) compound (based on its pKa). Naringin is a bitter tasting compound. Outside of the human body, Naringin is found, on average, in the highest concentration within a few different foods, such as rosemaries, grapefruit/pummelo hybrids, and grapefruits and in a lower concentration in grape wines, pummelo, and beers. Naringin has also been detected, but not quantified in, several different foods, such as citrus, limes, herbs and spices, common oregano, and mandarin orange (clementine, tangerine). This could make naringin a potential biomarker for the consumption of these foods. Both naringin and hesperetin, which are the aglycones of naringin and hesperidin, occur naturally in citrus fruits. Naringin is the major flavonoid glycoside in grapefruit and gives grapefruit juice its bitter taste. 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.
Structure
Data?1582752259
Synonyms
ValueSource
Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]ChEBI
Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucosideChEBI
Naringenin 7-O-neohesperidosideChEBI
NaringosideChEBI
Naringenin 7-O-[a-L-rhamnosyl-(1->2)-b-D-glucoside]Generator
Naringenin 7-O-[α-L-rhamnosyl-(1->2)-β-D-glucoside]Generator
Naringenin 7-O-a-L-rhamnosyl-(1->2)-b-D-glucosideGenerator
Naringenin 7-O-α-L-rhamnosyl-(1->2)-β-D-glucosideGenerator
4'5-DiOH-flavone-7-rhglucHMDB
Naringin hydrateHMDB
NobiletinHMDB
Naringenin-7-hesperidosideHMDB
Naringin sodiumHMDB
AurantiinHMDB
4',5,7-Trihydroxyflavanone 7-rhamnoglucosideHMDB
CyclorelHMDB
Naringin dihydrochalconeHMDB
Chemical FormulaC27H32O14
Average Molecular Weight580.5346
Monoisotopic Molecular Weight580.179205732
IUPAC Name(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
Traditional Namenaringin
CAS Registry Number10236-47-2
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
InChI Identifier
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
InChI KeyDFPMSGMNTNDNHN-ZPHOTFPESA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point83 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mL at 40 °CNot Available
LogP-0.44PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
Water Solubility4.06 g/LALOGPS
logP-0.24ALOGPS
logP-0.16ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.58ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area225.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity134.3 m³·mol⁻¹ChemAxon
Polarizability56.19 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-0920000000-350bda4f263e4440e76aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014j-0920000000-350bda4f263e4440e76aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-044j-9521280000-3e3e40b7d28b4e903216Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ei-9302015000-e97b650a0d6a1b78ddc3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0000090000-62ab85e8b85e9515ddc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (Shimadzu LC20A-IT-TOFMS) , Negativesplash10-004i-0000091000-2671e4ecb91933035e78Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0100090000-0c16a31fd116a04809ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00di-0290110000-a72cef11c1816469a269Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-00di-0290110000-a72cef11c1816469a269Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0000090000-d6285c4e4374990ed161Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0030290000-06238e4a98a4daad3265Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0030290000-06238e4a98a4daad3265Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0100090000-0c16a31fd116a04809ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00di-0290110000-a72cef11c1816469a269Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0000090000-4498c4e102c3c7d3d514Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0000090000-d6285c4e4374990ed161Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0030290000-06238e4a98a4daad3265Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0fk9-0690000000-3d8f024f57318d3dbca8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0fk9-2981000000-e103705338e8e8855307Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0290110000-a72cef11c1816469a269Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0000090000-4498c4e102c3c7d3d514Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0000090000-d6285c4e4374990ed161Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0030290000-06238e4a98a4daad3265Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-0390740000-ed6375341eb1bebac319Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0490200000-bbf5e62f8ba5ef5c55c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-0940000000-043fddfc9269db83e1f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02or-3592880000-a3ec8e8504154578e09fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-2691310000-865585e62bd05144335bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-7590000000-82ba5c0120e07b81e87bSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 208 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID208
FooDB IDFDB011866
KNApSAcK IDC00000983
Chemspider ID390868
KEGG Compound IDC09789
BioCyc IDNARINGIN
BiGG IDNot Available
Wikipedia LinkNaringin
METLIN ID3604
PubChem Compound442428
PDB IDNot Available
ChEBI ID28819
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Tanaka S, Sato T, Akimoto N, Yano M, Ito A: Prevention of UVB-induced photoinflammation and photoaging by a polymethoxy flavonoid, nobiletin, in human keratinocytes in vivo and in vitro. Biochem Pharmacol. 2004 Aug 1;68(3):433-9. [PubMed:15242810 ]
  2. Zhang J, Brodbelt JS: Screening flavonoid metabolites of naringin and narirutin in urine after human consumption of grapefruit juice by LC-MS and LC-MS/MS. Analyst. 2004 Dec;129(12):1227-33. Epub 2004 Oct 26. [PubMed:15565223 ]
  3. 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 ]
  4. Minagawa A, Otani Y, Kubota T, Wada N, Furukawa T, Kumai K, Kameyama K, Okada Y, Fujii M, Yano M, Sato T, Ito A, Kitajima M: The citrus flavonoid, nobiletin, inhibits peritoneal dissemination of human gastric carcinoma in SCID mice. Jpn J Cancer Res. 2001 Dec;92(12):1322-8. [PubMed:11749698 ]
  5. Ishii K, Furuta T, Kasuya Y: Mass spectrometric identification and high-performance liquid chromatographic determination of a flavonoid glycoside naringin in human urine. J Agric Food Chem. 2000 Jan;48(1):56-9. [PubMed:10637051 ]
  6. 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 ]
  7. Kanaze FI, Kokkalou E, Georgarakis M, Niopas I: A validated solid-phase extraction HPLC method for the simultaneous determination of the citrus flavanone aglycones hesperetin and naringenin in urine. J Pharm Biomed Anal. 2004 Sep 21;36(1):175-81. [PubMed:15351063 ]
  8. Lin N, Sato T, Takayama Y, Mimaki Y, Sashida Y, Yano M, Ito A: Novel anti-inflammatory actions of nobiletin, a citrus polymethoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Biochem Pharmacol. 2003 Jun 15;65(12):2065-71. [PubMed:12787887 ]