Record Information
Version1.0
Creation date2010-04-08 22:04:38 UTC
Update date2019-11-26 02:55:04 UTC
Primary IDFDB000608
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsorhamnetin 7-rhamnoside
DescriptionIsorhamnetin 7-rhamnoside is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Isorhamnetin 7-rhamnoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Isorhamnetin 7-rhamnoside can be found in sea-buckthornberry, which makes isorhamnetin 7-rhamnoside a potential biomarker for the consumption of this food product.
CAS Number17331-72-5
Structure
Thumb
Synonyms
SynonymSource
Isorhamnetin 7-rhamnosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP1.29ALOGPS
logP1.08ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)7.09ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area175.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity111.95 m³·mol⁻¹ChemAxon
Polarizability45.3 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H22O11
IUPAC name3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one
InChI IdentifierInChI=1S/C22H22O11/c1-8-16(25)18(27)20(29)22(31-8)32-10-6-12(24)15-14(7-10)33-21(19(28)17(15)26)9-3-4-11(23)13(5-9)30-2/h3-8,16,18,20,22-25,27-29H,1-2H3
InChI KeyXLQFMBLUUSGXQY-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(OC3OC(C)C(O)C(O)C3O)C=C2O1
Average Molecular Weight462.4035
Monoisotopic Molecular Weight462.116211546
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
  • 3-hydroxyflavone
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • 1-benzopyran
  • Methoxyphenol
  • Benzopyran
  • Methoxybenzene
  • Phenol ether
  • Phenoxy compound
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.14%; H 4.80%; O 38.06%DFC
Melting PointMp 248-250°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -122 (EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsorhamnetin 7-rhamnoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4j-9102600000-52846fea4e8a76a47c6dSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ta-0139800000-e6289e3cae147ece5699Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0179100000-72efb0dfd43b03ed62e4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7a-2695000000-f9b0346daf1d8f16f3c7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-1116900000-296d7fb1ce532cb78da3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2279300000-36bb9f0ef93896f64f2dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-2293000000-a52c6072d2acc1c98c4cSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBFD21-N:BFD30-P
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00005531
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.