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Record Information
Version3.6
Creation Date2006-05-22 15:12:20 UTC
Update Date2016-02-11 01:05:53 UTC
HMDB IDHMDB02927
Secondary Accession NumbersNone
Metabolite Identification
Common NameNaringin
DescriptionNaringin 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.
Structure
Thumb
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
4'5-DiOH-flavone-7-rhglucHMDB
Naringin hydrateHMDB
NobiletinHMDB
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 KeyInChIKey=DFPMSGMNTNDNHN-ZPHOTFPESA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydroxyflavonoid
  • Flavanone
  • Fatty acyl glycoside
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Saccharide
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Plant
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateLiquid
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 mg/mLALOGPS
logP-0.24ALOGPS
logP-0.16ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.32ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area225.06 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity134.3 m3·mol-1ChemAxon
Polarizability56.19 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0000090000-62ab85e8b85e9515ddc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (Shimadzu LC20A-IT-TOFMS) , Negativesplash10-004i-0000091000-2671e4ecb91933035e78View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location
  • Epidermis
  • Fibroblasts
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 208
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID208
Phenol Explorer Metabolite ID208
FoodDB IDFDB011866
KNApSAcK IDC00000983
Chemspider ID390868
KEGG Compound IDC09789
BioCyc IDCPD-7067
BiGG IDNot Available
Wikipedia LinkNaringin
NuGOwiki LinkHMDB02927
Metagene LinkHMDB02927
METLIN ID3604
PubChem Compound442428
PDB IDNot Available
ChEBI ID28819
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [12787887 ]
  2. 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. [8891919 ]
  3. 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. [7586927 ]
  4. 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. [15242810 ]
  5. 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. [15565223 ]
  6. 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. [11749698 ]
  7. 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. [10637051 ]
  8. 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. [15351063 ]