You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:40:51 UTC
Update Date2019-07-23 06:34:59 UTC
HMDB IDHMDB0041757
Secondary Accession Numbers
  • HMDB41757
Metabolite Identification
Common NameIsorhamnetin 4'-O-glucuronide
DescriptionIsorhamnetin 4'-O-glucuronide belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Isorhamnetin 4'-glucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ). Isorhamnetin 4'-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863699
Synonyms
ValueSource
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[2-methoxy-4-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylateGenerator
Chemical FormulaC22H20O13
Average Molecular Weight492.3864
Monoisotopic Molecular Weight492.090390726
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-methoxy-4-(3,5,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-methoxy-4-(3,5,7-trihydroxy-4-oxochromen-2-yl)phenoxy]oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=CC(=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C22H20O13/c1-32-11-4-7(19-16(27)14(25)13-9(24)5-8(23)6-12(13)33-19)2-3-10(11)34-22-18(29)15(26)17(28)20(35-22)21(30)31/h2-6,15,17-18,20,22-24,26-29H,1H3,(H,30,31)/t15-,17-,18+,20-,22+/m0/s1
InChI KeyNCHMCZDLVWDQLC-YWQONGFDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-7-o-glucuronide
  • Flavonoid-7-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavanone
  • Flavan
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Aryl alkyl ketone
  • Aryl ketone
  • Beta-hydroxy acid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Acetal
  • Ether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility1.23 g/LALOGPS
logP1.02ALOGPS
logP0.35ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area212.67 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.36 m³·mol⁻¹ChemAxon
Polarizability45.9 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05y3-9006500000-8a4f562dff3f10d4afceSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-9511218000-8d504fa2279921ef2af2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-016r-0037900000-45d3eeb51c8cd1c82eb6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0169100000-c203b70cccba15614cefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fya-0943000000-1a3eb9e06507ca21534aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kf-1204900000-066f232a675d5b5ce5cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2369700000-e54874d050b380e48965Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016s-5986000000-a31eb3e41d9fc393ac23Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 822 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 822 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 822 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 822 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029927
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound57331044
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 ]