Record Information
Version1.0
Creation date2010-04-08 22:09:52 UTC
Update date2019-11-26 03:05:37 UTC
Primary IDFDB011868
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNarirutin
DescriptionNarirutin 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. Narirutin is a bland tasting compound. Narirutin is found, on average, in the highest concentration within a few different foods, such as peppermints (Mentha X piperita), grapefruit/pummelo hybrids (Citrus paradisi X Citrus maxima), and grapefruits (Citrus X paradisi) and in a lower concentration in mandarin orange (clementine, tangerine), lemons (Citrus limon), and sweet oranges (Citrus sinensis). Narirutin has also been detected, but not quantified in, several different foods, such as green tea, fruit juice, teas (Camellia sinensis), black tea, and red tea. This could make narirutin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Narirutin.
CAS Number14259-46-2
Structure
Thumb
Synonyms
SynonymSource
IsonaringeninHMDB
IsonaringinHMDB
Naringenin 7-O-rutinosideHMDB
Naringenin 7-rutinosideHMDB
Narirutindb_source
Predicted PropertiesNot Available
Chemical FormulaC27H32O14
IUPAC name
InChI IdentifierInChI=1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3
InChI KeyHXTFHSYLYXVTHC-UHFFFAOYSA-N
Isomeric SMILESCC1OC(OCC2OC(OC3=CC(O)=C4C(=O)CC(OC4=C3)C3=CC=C(O)C=C3)C(O)C(O)C2O)C(O)C(O)C1O
Average Molecular Weight580.5346
Monoisotopic Molecular Weight580.179205732
Classification
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
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.86%; H 5.56%; O 38.58%DFC
Melting PointMp 160-165°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID77296
ChEMBL IDNot Available
KEGG Compound IDC09793
Pubchem Compound ID85704
Pubchem Substance IDNot Available
ChEBI ID28705
Phenol-Explorer ID209
DrugBank IDNot Available
HMDB IDHMDB33740
CRC / DFC (Dictionary of Food Compounds) IDBFM77-B:HBH89-T
EAFUS IDNot Available
Dr. Duke IDNARIRUTIN|NARINGIN-7-O-ALPHA-L-RHAMNO-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00000984
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1057341
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
oviposition stimulantDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bland
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
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.