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Isorhamnetin 7-glucoside (FDB000606)

Record Information
Version1.0
Creation date2010-04-08 22:04:38 UTC
Update date2020-02-24 19:10:10 UTC
Primary IDFDB000606
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsorhamnetin 7-glucoside
DescriptionIsorhamnetin 7-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. Isorhamnetin 7-glucoside is found, on average, in the highest concentration within sea-buckthornberries (Hippophae rhamnoides). Isorhamnetin 7-glucoside has also been detected, but not quantified in, brassicas and german camomiles (Matricaria recutita). This could make isorhamnetin 7-glucoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isorhamnetin 7-glucoside.
CAS Number6743-96-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.07 g/LALOGPS
logP0.49ALOGPS
logP0.034ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)8.08ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area195.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.49 m³·mol⁻¹ChemAxon
Polarizability46.01 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H22O12
IUPAC name3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
InChI IdentifierInChI=1S/C22H22O12/c1-31-12-4-8(2-3-10(12)24)21-19(29)17(27)15-11(25)5-9(6-13(15)33-21)32-22-20(30)18(28)16(26)14(7-23)34-22/h2-6,14,16,18,20,22-26,28-30H,7H2,1H3
InChI KeyYCUNOXSUHVGZRI-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(=CC=C1O)C1=C(O)C(=O)C2=C(O)C=C(OC3OC(CO)C(O)C(O)C3O)C=C2O1
Average Molecular Weight478.4029
Monoisotopic Molecular Weight478.111126168
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
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.23%; H 4.63%; O 40.13%DFC
Melting PointMp 253-255°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +40.5 (c, 0.1 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsorhamnetin 7-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08mj-9303700000-2fe1f169d490055cc907Spectrum
Predicted GC-MSIsorhamnetin 7-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0059-3231019000-1b71b4182762379e298fSpectrum
Predicted GC-MSIsorhamnetin 7-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-0129800000-d4bf0d6e37c415d3cd892015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0179100000-439025f1676b507dd3582015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frb-3796000000-9fb0f620e31d7385a0522015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-0215900000-a05ce1b8b29a02437ea52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2279300000-18d8ebbf336a412cd2ae2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-2293000000-295e4e6346c2ea0386e12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-0009400000-f9e020672b78a8b5d2f72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009100000-6d263fc476cff759693e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0009000000-d4d9bcf99cd318117dc62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-36b7563274bb641ad9b02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0005900000-560bf2b0d639545ffeb42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0009100000-105186b5606fe7b1430b2021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6455477
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID306
DrugBank IDNot Available
HMDB IDHMDB29479
CRC / DFC (Dictionary of Food Compounds) IDBFD21-N:BFD26-S
EAFUS IDNot Available
Dr. Duke IDISORHAMNETIN-7-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00005530
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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).