Record Information
Version1.0
Creation date2010-04-08 22:12:35 UTC
Update date2019-11-26 03:13:37 UTC
Primary IDFDB016688
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNarirutin 4'-glucoside
DescriptionNarirutin 4'-glucoside 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 4'-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Narirutin 4'-glucoside is found, on average, in the highest concentration within grapefruit/pummelo hybrids. Narirutin 4'-glucoside has also been detected, but not quantified in, citrus. This could make narirutin 4'-glucoside a potential biomarker for the consumption of these foods.
CAS Number17257-22-6
Structure
Thumb
Synonyms
SynonymSource
Naringenin 4'-glucoside 7-rutinosideHMDB
Narirutin 4'-glucosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility5.04 g/LALOGPS
logP-0.92ALOGPS
logP-2.4ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.64ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area304.21 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity166.45 m³·mol⁻¹ChemAxon
Polarizability72.86 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC33H42O19
IUPAC name5-hydroxy-2-(4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-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
InChI IdentifierInChI=1S/C33H42O19/c1-11-22(37)25(40)28(43)31(47-11)46-10-20-24(39)27(42)30(45)33(52-20)49-14-6-15(35)21-16(36)8-17(50-18(21)7-14)12-2-4-13(5-3-12)48-32-29(44)26(41)23(38)19(9-34)51-32/h2-7,11,17,19-20,22-35,37-45H,8-10H2,1H3
InChI KeyKQUWJUNIYQVHCG-UHFFFAOYSA-N
Isomeric SMILESCC1OC(OCC2OC(OC3=CC4=C(C(=O)CC(O4)C4=CC=C(OC5OC(CO)C(O)C(O)C5O)C=C4)C(O)=C3)C(O)C(O)C2O)C(O)C(O)C1O
Average Molecular Weight742.68
Monoisotopic Molecular Weight742.232029132
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
  • 5-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Aryl alkyl ketone
  • Phenol ether
  • Aryl ketone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Oxane
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Ether
  • Acetal
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 53.37%; H 5.70%; O 40.93%DFC
Melting PointMp 189-200°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -62.6 (c, 0.92 in Py)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02dr-0250980700-f55e78ea75927a165536JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0490730000-12bbf6f4baf1cfafb18bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0890310100-35960c75e761ab4cc52cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-4622660900-9418ef8dad17ab5b8d4fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03l1-4942750400-9fdd745f59241e62e042JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0459-4493510000-582b88fc33391d45ffd3JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID215
DrugBank IDNot Available
HMDB IDHMDB37584
CRC / DFC (Dictionary of Food Compounds) IDBFM77-B:KSJ52-J
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00008386
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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.