Isorhamnetin 3-glucuronide (CHEM031198)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:28:19 UTC
Update Date2016-11-09 01:19:13 UTC
Accession NumberCHEM031198
Identification
Common NameIsorhamnetin 3-glucuronide
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Chemical FormulaC22H20O13
Average Molecular Mass492.386 g/mol
Monoisotopic Mass492.090 g/mol
CAS Registry Number36687-76-0
IUPAC Name6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-{[5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILESCOC1=CC(=CC=C1O)C1=C(OC2OC(C(O)C(O)C2O)C(O)=O)C(=O)C2=C(O)C=C(O)C=C2O1
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-9200057000-7614097280c3710a64e8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05du-9005500000-6379986d10307a8f9dfdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016u-0107900000-a732d1ac0de974a50a42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0149100000-384880601fefd9d20156Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy0-2889000000-2c64dbab60166eaf0a69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kf-0104900000-5a1f25a67aa31c9739d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2179500000-4c473fb06bffa7fe8960Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014s-3394000000-6824da5c27878f3357bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009200000-2b4b62892313ced15038Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014o-0009900000-a61a1b3bac4a385c5579Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0009000000-235a2c69093cac80b556Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-cd56e63b524a91bda55aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0005900000-0c9687b43b44a7f81bb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0019100000-b8b1f019bc388c4add89Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0126576
FooDB IDFDB016876
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID45782983
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis)