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Isorhamnetin 3-O-b-D-glucopyranoside (FDB021629)

Record Information
Version1.0
Creation date2011-03-17 23:25:05 UTC
Update date2020-02-24 19:11:05 UTC
Primary IDFDB021629
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsorhamnetin 3-O-b-D-glucopyranoside
DescriptionIsorhamnetin 3-o-b-d-glucopyranoside, also known as isorhamnetin-3-O-galactoside, is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Thus, isorhamnetin 3-o-b-d-glucopyranoside is considered to be a flavonoid lipid molecule. Isorhamnetin 3-o-b-d-glucopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Isorhamnetin 3-o-b-d-glucopyranoside can be found in a number of food items such as common grape, caraway, ginkgo nuts, and grape wine, which makes isorhamnetin 3-o-b-d-glucopyranoside a potential biomarker for the consumption of these food products.
CAS Number5041-82-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
logP0.64ALOGPS
logP0.0011ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area195.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.76 m³·mol⁻¹ChemAxon
Polarizability45.37 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H22O12
IUPAC name5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[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)25)20-21(17(28)15-11(26)5-9(24)6-13(15)32-20)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3
InChI KeyCQLRUIIRRZYHHS-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1=C(OC2OC(CO)C(O)C(O)C2O)C(=O)C2=C(O)C=C(O)C=C2O1
Average Molecular Weight478.4029
Monoisotopic Molecular Weight478.111126168
Classification
Description Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Methoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Alkyl aryl ether
  • 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 Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.23%; H 4.63%; O 40.13%DFC
Melting PointMp 215-218° (177-179°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -21.7 (c, 0.06 in MeOH)DFC
Spectroscopic UV Data359 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSIsorhamnetin 3-O-b-D-glucopyranoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-5300009000-e04d5f47e459ead0d406Spectrum
Predicted GC-MSIsorhamnetin 3-O-b-D-glucopyranoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08mi-9303700000-181ed66d9fe6d203d36bSpectrum
Predicted GC-MSIsorhamnetin 3-O-b-D-glucopyranoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-0128900000-e6421469a7b4026538f92019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0289100000-f1cea983648895b75eb42019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0frj-2955000000-89853165ea8f69caaa802019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-0205900000-bdb075fa291a5c58001a2019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2579500000-68f0255963bd987b4fe72019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00mt-4973000000-277bad5c86d0cdf85b922019-02-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-eb5beabac8fd02bbd3152021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0005900000-2e73155f50b1e219d0c32021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0019100000-eaa122d134bed43dafd72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009200000-b7d831e7c041b40896642021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0190-0009900000-6eb06f25836eb1f2fbe22021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0009000000-235a2c69093cac80b5562021-09-25View Spectrum
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 ID326
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDODR39-P:KQZ32-R
EAFUS IDNot Available
Dr. Duke IDISORHAMNETIN-3-O-BETA-D-GLUCOSIDE|ISORHAMNETIN-3-BETA-D-GLUCOSIDE|ISORHAMNETIN-3-GLUCOSIDE|ISORHAMNETIN-3-O-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00005525
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 ID326
Duplicate IDSNot Available
Old DFC IDSBFD21-N:BFD25-R
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— 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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.