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Showing metabocard for Naringenin 4'-O-glucuronide (HMDB0041759)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-12 03:40:58 UTC
Update Date2019-07-23 06:34:59 UTC
HMDB IDHMDB0041759
Secondary Accession Numbers
  • HMDB0029208
  • HMDB29208
  • HMDB41759
Metabolite Identification
Common NameNaringenin 4'-O-glucuronide
DescriptionNaringenin 4'-O-glucuronide belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid. Naringenin 4'-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863699
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,3S,4S,5R,6S)-6-[4-(5,7-Dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylateGenerator
Chemical FormulaC21H20O11
Average Molecular Weight448.3769
Monoisotopic Molecular Weight448.100561482
IUPAC Name(2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-[4-(5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number158196-35-1
SMILES
O[C@@H]1[C@@H](O)[C@H](OC2=CC=C(C=C2)C2CC(=O)C3=C(O2)C=C(O)C=C3O)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C21H20O11/c22-9-5-11(23)15-12(24)7-13(31-14(15)6-9)8-1-3-10(4-2-8)30-21-18(27)16(25)17(26)19(32-21)20(28)29/h1-6,13,16-19,21-23,25-27H,7H2,(H,28,29)/t13?,16-,17-,18+,19-,21+/m0/s1
InChI KeyDFIUUCDSSKATFP-DNPGXZAYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-4p-o-glucuronide
  • Flavanone
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • Chromone
  • O-glycosyl compound
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Phenol ether
  • Aryl ketone
  • Phenoxy compound
  • Aryl alkyl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Beta-hydroxy acid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyran
  • Oxane
  • Benzenoid
  • Hydroxy acid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.48 g/LALOGPS
logP0.73ALOGPS
logP0.89ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area183.21 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.3 m³·mol⁻¹ChemAxon
Polarizability42.53 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9127300000-c6835872bfd70e22889bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0uka-3062159000-c2aec4f11cbaea5cef50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ea-0290700000-5f5ea6b829455c17d870Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-0490000000-4c70573c04a73fd85083Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmi-1930000000-008fa0b3097795aaf03aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fdk-1251900000-16bbf6f0839e8d3fc4c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2391200000-e011276b61a2b2625c86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-5590000000-4a1cbbb1494a41016d74Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    		 details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal    		 details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal    		 details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal    		 details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal    		 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 796 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 796 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 796 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 796 details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB029929
    KNApSAcK IDNot Available
    Chemspider IDNot Available
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound91312540
    PDB IDNot Available
    ChEBI IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]