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Showing Compound Isorhamnetin 3-glucuronide (FDB016876)

Record Information
Version1.0
Creation date2010-04-08 22:12:42 UTC
Update date2020-02-24 19:11:05 UTC
Primary IDFDB016876
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsorhamnetin 3-glucuronide
Description6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is a member of the class of compounds known as flavonoid-3-o-glucuronides. Flavonoid-3-o-glucuronides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position. 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid can be found in a number of food items such as cloudberry, dill, strawberry, and chicory, which makes 6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4h-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid a potential biomarker for the consumption of these food products.
CAS Number36687-76-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.71 g/LALOGPS
logP1.4ALOGPS
logP0.32ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.65ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area212.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.63 m³·mol⁻¹ChemAxon
Polarizability45.09 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H20O13
IUPAC name6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI IdentifierInChI=1S/C22H20O13/c1-32-11-4-7(2-3-9(11)24)18-19(14(26)13-10(25)5-8(23)6-12(13)33-18)34-22-17(29)15(27)16(28)20(35-22)21(30)31/h2-6,15-17,20,22-25,27-29H,1H3,(H,30,31)
InChI KeyVVZWHOMBDMMRSC-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C(=O)C2=C(O)C=C(O)C=C2O1
Average Molecular Weight492.3864
Monoisotopic Molecular Weight492.090390726
Classification
Description Belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-3-o-glucuronide
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Methoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Phenol
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    Predicted GC-MSIsorhamnetin 3-glucuronide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9200057000-7614097280c3710a64e8Spectrum
    Predicted GC-MSIsorhamnetin 3-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05du-9005500000-6379986d10307a8f9dfdSpectrum
    Predicted GC-MSIsorhamnetin 3-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSIsorhamnetin 3-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016u-0107900000-a732d1ac0de974a50a422016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0149100000-384880601fefd9d201562016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy0-2889000000-2c64dbab60166eaf0a692016-08-01View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kf-0104900000-5a1f25a67aa31c9739d12016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2179500000-4c473fb06bffa7fe89602016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014s-3394000000-6824da5c27878f3357bf2016-08-03View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009200000-2b4b62892313ced150382021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014o-0009900000-a61a1b3bac4a385c55792021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0009000000-235a2c69093cac80b5562021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-cd56e63b524a91bda55a2021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0005900000-0c9687b43b44a7f81bb42021-09-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0019100000-b8b1f019bc388c4add892021-09-24View Spectrum
    NMRNot Available
    ChemSpider IDNot Available
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound ID5491630
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID331
    DrugBank IDNot Available
    HMDB IDNot Available
    CRC / DFC (Dictionary of Food Compounds) IDBFD21-N:KTS20-Y
    EAFUS IDNot Available
    Dr. Duke IDISORHAMNETIN-3-GLUCURONIDE|3-GLUCURONIDE-ISORHAMNETIN
    BIGG IDNot Available
    KNApSAcK IDC00005527
    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 ID331
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    ChicoryExpected but not quantifiedNot AvailableDUKE
    DillExpected but not quantifiedNot AvailableDUKE, KNAPSACK
    Showing 1 to 2 of 2 entries
    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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
    — 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.