Posted inUncategorized

Quercetin 3-O-glucuronide

July 21, 2017
Common Name

Quercetin 3-O-glucuronide Description

Quercetin 3-O-glucuronide is a cocoa and tea metabolite in plasma and urine. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Structure for HMDB29212 (Quercetin 3-O-glucuronide)

Synonyms

Value Source MiquelianinHMDB Quercetin 3-glucuronideHMDB Quercetin-3-glucuronidequercetin glucuronideHMDB Quercetin 3-O-beta-D-glucopyranosideMeSH Quercetin 3-O-beta-glucopyranosideMeSH Quercetin 3-O-glucopyranosideMeSH

Chemical Formlia

C21H18O13 Average Molecliar Weight

478.3598 Monoisotopic Molecliar Weight

478.074740662 IUPAC Name

6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid Traditional Name

miquelianin CAS Registry Number

22688-79-5 SMILES

OC1C(O)C(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)OC(C1O)C(O)=O

InChI Identifier

InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)

InChI Key

DUBCCGAQYVUYEU-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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. Kingdom

Chemical entities Super Class

Organic compounds Class

Phenylpropanoids and polyketides Sub Class

Flavonoids Direct Parent

Flavonoid-3-O-glucuronides Alternative Parents

  • Flavonoid-3-O-glycosides
  • 3-hydroxyflavonoids
  • 4-hydroxyflavonoids
  • 5-hydroxyflavonoids
  • 7-hydroxyflavonoids
  • Flavones
  • O-glucuronides
  • Hexoses
  • O-glycosyl compounds
  • Chromones
  • Catechols
  • 1-hydroxy-2-unsubstituted benzenoids
  • 1-hydroxy-4-unsubstituted benzenoids
  • Pyranones and derivatives
  • Beta hydroxy acids and derivatives
  • Oxanes
  • Benzene and substituted derivatives
  • Vinylogous acids
  • Heteroaromatic compounds
  • Secondary alcohols
  • Carboxylic acids
  • Monocarboxylic acids and derivatives
  • Acetals
  • Oxacyclic compounds
  • Polyols
  • Carbonyl compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Flavonoid-3-o-glucuronide
  • Flavonoid-3-o-glycoside
  • 3'-hydroxyflavonoid
  • 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
  • Catechol
  • Beta-hydroxy acid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monosaccharide
  • Oxane
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Endogenous

    • Biofunction

  • Nutrient
  • Waste products

    • Application

    Not Available Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility2.4 mg/mLALOGPS logP1.37ALOGPS logP0.18ChemAxon logS-2.3ALOGPS pKa (Strongest Acidic)2.65ChemAxon pKa (Strongest Basic)-3.7ChemAxon Physiological Charge-2ChemAxon Hydrogen Acceptor Count13ChemAxon Hydrogen Donor Count8ChemAxon Polar Surface Area223.67 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity109.14 m3·mol-1ChemAxon Polarizability43.27 Å3ChemAxon Number of Rings4ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

    Not Available Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

  • Kidney
  • Liver

    • Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 16869998

    • details BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 15595664

    • details BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 17015248

    • details UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 16869998

    • details UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 15595664

    • details UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 17015248

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    330 Phenol Explorer Metabolite ID

    330 FoodDB ID

    FDB017092 KNApSAcK ID

    C00005376 Chemspider ID

    10176995 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Quercetin_glucuronide NuGOwiki Link

    HMDB29212 Metagene Link

    HMDB29212 METLIN ID

    Not Available PubChem Compound

    12004528 PDB ID

    Not Available ChEBI ID

    1030566

    Product: trans-Trimethoxyresveratrol

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
    Gene Name:
    UGT2B4
    Uniprot ID:
    P06133
    Molecular weight:
    60512.035
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
    Gene Name:
    UGT1A4
    Uniprot ID:
    P22310
    Molecular weight:
    60024.535
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
    Gene Name:
    UGT2B7
    Uniprot ID:
    P16662
    Molecular weight:
    60720.15
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
    Gene Name:
    UGT1A9
    Uniprot ID:
    O60656
    Molecular weight:
    59940.495
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
    Gene Name:
    UGT1A6
    Uniprot ID:
    P19224
    Molecular weight:
    60750.215

    PMID: 20377617

    Last updated on
    Posted inUncategorized

    Quercetin 3-O-glucuronide

    July 21, 2017
    Common Name

    Quercetin 3-O-glucuronide Description

    Quercetin 3-O-glucuronide is a cocoa and tea metabolite in plasma and urine. Structure

    MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

    Structure for HMDB29212 (Quercetin 3-O-glucuronide)

    Synonyms

    Value Source MiquelianinHMDB Quercetin 3-glucuronideHMDB Quercetin-3-glucuronidequercetin glucuronideHMDB Quercetin 3-O-beta-D-glucopyranosideMeSH Quercetin 3-O-beta-glucopyranosideMeSH Quercetin 3-O-glucopyranosideMeSH

    Chemical Formlia

    C21H18O13 Average Molecliar Weight

    478.3598 Monoisotopic Molecliar Weight

    478.074740662 IUPAC Name

    6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid Traditional Name

    miquelianin CAS Registry Number

    22688-79-5 SMILES

    OC1C(O)C(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C(O)=C2)OC(C1O)C(O)=O

    InChI Identifier

    InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)

    InChI Key

    DUBCCGAQYVUYEU-UHFFFAOYSA-N Chemical Taxonomy Description

    This compound belongs to the class of chemical entities 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. Kingdom

    Chemical entities Super Class

    Organic compounds Class

    Phenylpropanoids and polyketides Sub Class

    Flavonoids Direct Parent

    Flavonoid-3-O-glucuronides Alternative Parents

  • Flavonoid-3-O-glycosides
  • 3-hydroxyflavonoids
  • 4-hydroxyflavonoids
  • 5-hydroxyflavonoids
  • 7-hydroxyflavonoids
  • Flavones
  • O-glucuronides
  • Hexoses
  • O-glycosyl compounds
  • Chromones
  • Catechols
  • 1-hydroxy-2-unsubstituted benzenoids
  • 1-hydroxy-4-unsubstituted benzenoids
  • Pyranones and derivatives
  • Beta hydroxy acids and derivatives
  • Oxanes
  • Benzene and substituted derivatives
  • Vinylogous acids
  • Heteroaromatic compounds
  • Secondary alcohols
  • Carboxylic acids
  • Monocarboxylic acids and derivatives
  • Acetals
  • Oxacyclic compounds
  • Polyols
  • Carbonyl compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Flavonoid-3-o-glucuronide
  • Flavonoid-3-o-glycoside
  • 3'-hydroxyflavonoid
  • 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
  • Catechol
  • Beta-hydroxy acid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monosaccharide
  • Oxane
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Endogenous

    • Biofunction

  • Nutrient
  • Waste products

    • Application

    Not Available Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility2.4 mg/mLALOGPS logP1.37ALOGPS logP0.18ChemAxon logS-2.3ALOGPS pKa (Strongest Acidic)2.65ChemAxon pKa (Strongest Basic)-3.7ChemAxon Physiological Charge-2ChemAxon Hydrogen Acceptor Count13ChemAxon Hydrogen Donor Count8ChemAxon Polar Surface Area223.67 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity109.14 m3·mol-1ChemAxon Polarizability43.27 Å3ChemAxon Number of Rings4ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

    Not Available Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

  • Kidney
  • Liver

    • Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 16869998

    • details BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 15595664

    • details BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 17015248

    • details UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 16869998

    • details UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 15595664

    • details UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 330

  • 17015248

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    330 Phenol Explorer Metabolite ID

    330 FoodDB ID

    FDB017092 KNApSAcK ID

    C00005376 Chemspider ID

    10176995 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Quercetin_glucuronide NuGOwiki Link

    HMDB29212 Metagene Link

    HMDB29212 METLIN ID

    Not Available PubChem Compound

    12004528 PDB ID

    Not Available ChEBI ID

    1030566

    Product: trans-Trimethoxyresveratrol

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
    Gene Name:
    UGT2B4
    Uniprot ID:
    P06133
    Molecular weight:
    60512.035
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
    Gene Name:
    UGT1A4
    Uniprot ID:
    P22310
    Molecular weight:
    60024.535
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
    Gene Name:
    UGT2B7
    Uniprot ID:
    P16662
    Molecular weight:
    60720.15
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
    Gene Name:
    UGT1A9
    Uniprot ID:
    O60656
    Molecular weight:
    59940.495
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
    Gene Name:
    UGT1A6
    Uniprot ID:
    P19224
    Molecular weight:
    60750.215

    PMID: 20377617

    Last updated on