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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:29:59 UTC
Update Date2022-03-07 02:53:50 UTC
HMDB IDHMDB0033740
Secondary Accession Numbers
  • HMDB33740
Metabolite Identification
Common 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 lemons (Citrus limon), mandarin orange (clementine, tangerine), and limes (Citrus aurantiifolia). Narirutin has also been detected, but not quantified in, several different foods, such as red tea, pummelos (Citrus maxima), teas (Camellia sinensis), globe artichokes (Cynara scolymus), and green 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.
Structure
Thumb
Synonyms
ValueSource
IsonaringeninHMDB
IsonaringinHMDB
Naringenin 7-O-rutinosideHMDB
Naringenin 7-rutinosideHMDB
Chemical FormulaC27H32O14
Average Molecular Weight580.5346
Monoisotopic Molecular Weight580.179205732
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5-hydroxy-2-(4-hydroxyphenyl)-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-2,3-dihydro-1-benzopyran-4-one
CAS Registry Number14259-46-2
SMILES
CC1OC(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
InChI Identifier
InChI=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
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
  • 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
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point160 - 165 °CNot Available
Boiling Point924.00 to 925.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2369 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.522 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011868
KNApSAcK IDC00000984
Chemspider ID77296
KEGG Compound IDC09793
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNarirutin
METLIN IDNot Available
PubChem Compound85704
PDB IDNot Available
ChEBI ID28705
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1057341
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Funaguchi N, Ohno Y, La BL, Asai T, Yuhgetsu H, Sawada M, Takemura G, Minatoguchi S, Fujiwara T, Fujiwara H: Narirutin inhibits airway inflammation in an allergic mouse model. Clin Exp Pharmacol Physiol. 2007 Aug;34(8):766-70. [PubMed:17600554 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .