Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2019-11-26 03:05:37 UTC
Primary IDFDB011866
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNaringin
Descriptionobtained 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.
CAS Number10236-47-2
Structure
Thumb
Synonyms
SynonymSource
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
Isohesperidindb_source
Naringenin 7-neohesperidosidedb_source
Naringindb_source
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
Chemical FormulaC27H32O14
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
InChI IdentifierInChI=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
Isomeric SMILESC[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
Average Molecular Weight580.5346
Monoisotopic Molecular Weight580.179205732
Classification
Description Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty alcohol
  • Sugar alcohol
  • Oxane
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 55.86%; H 5.56%; O 38.58%DFC
Melting PointMp 171° (dihydrate)DFC
Boiling PointNot Available
Experimental Water Solubility1 mg/mL at 40 oCMERCK INDEX (1996)
Experimental logP-0.44PERRISSOUD,D & TESTA,B (1986)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]19D -82.1 (EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSNaringin, non-derivatized, GC-MS Spectrumsplash10-014j-0920000000-350bda4f263e4440e76aSpectrum
GC-MSNaringin, non-derivatized, GC-MS Spectrumsplash10-014j-0920000000-350bda4f263e4440e76aSpectrum
Predicted GC-MSNaringin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-044j-9521280000-3e3e40b7d28b4e903216Spectrum
Predicted GC-MSNaringin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ei-9302015000-e97b650a0d6a1b78ddc3Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0000090000-62ab85e8b85e9515ddc1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (Shimadzu LC20A-IT-TOFMS) , Negativesplash10-004i-0000091000-2671e4ecb91933035e78Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0100090000-0c16a31fd116a04809ffSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00di-0290110000-a72cef11c1816469a269Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-00di-0290110000-a72cef11c1816469a269Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0000090000-d6285c4e4374990ed161Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0030290000-06238e4a98a4daad3265Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0030290000-06238e4a98a4daad3265Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0100090000-0c16a31fd116a04809ffSpectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-00di-0290110000-a72cef11c1816469a269Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0000090000-4498c4e102c3c7d3d514Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0000090000-d6285c4e4374990ed161Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0030290000-06238e4a98a4daad3265Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0fk9-0690000000-3d8f024f57318d3dbca8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0fk9-2981000000-e103705338e8e8855307Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00di-0290110000-a72cef11c1816469a269Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0000090000-4498c4e102c3c7d3d514Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0000090000-d6285c4e4374990ed161Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0030290000-06238e4a98a4daad3265Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-0390740000-ed6375341eb1bebac319Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0490200000-bbf5e62f8ba5ef5c55c6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-0940000000-043fddfc9269db83e1f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02or-3592880000-a3ec8e8504154578e09fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-2691310000-865585e62bd05144335bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-7590000000-82ba5c0120e07b81e87bSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID390868
ChEMBL IDCHEMBL451532
KEGG Compound IDC09789
Pubchem Compound ID442428
Pubchem Substance IDNot Available
ChEBI ID28819
Phenol-Explorer ID208
DrugBank IDNot Available
HMDB IDHMDB02927
CRC / DFC (Dictionary of Food Compounds) IDBFM77-B:HBH63-H
EAFUS IDNot Available
Dr. Duke IDNARINGOSIDE|NARINGIN
BIGG IDNot Available
KNApSAcK IDC00000983
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNaringin
Phenol-Explorer Metabolite ID208
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An 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).DUKE
anti dermatitic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti mutagenicDUKE
anti neuropathicDUKE
antioxidant22586 A 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.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
myorelaxantDUKE
oviposition stimulantDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.