Luteolin 7-glucuronide (CHEM031818)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:56:32 UTC
Update Date2016-11-09 01:19:20 UTC
Accession NumberCHEM031818
Identification
Common NameLuteolin 7-glucuronide
ClassSmall Molecule
DescriptionA luteolin glucosiduronic acid consisting of luteolin having a beta-D-glucosiduronic acid residue attached at the 7-position.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Cyanidenon-7-O-beta-D-glucuronic acidChEBI
Luteolin 7-O-beta-D-glucuronopyranosideChEBI
Luteolin 7-O-glucuronideChEBI
Luteolin 7-O-beta-D-glucuronideKegg
Cyanidenon-7-O-b-D-glucuronateGenerator
Cyanidenon-7-O-b-D-glucuronic acidGenerator
Cyanidenon-7-O-beta-D-glucuronateGenerator
Cyanidenon-7-O-β-D-glucuronateGenerator
Cyanidenon-7-O-β-D-glucuronic acidGenerator
Luteolin 7-O-b-D-glucuronopyranosideGenerator
Luteolin 7-O-β-D-glucuronopyranosideGenerator
Luteolin 7-O-b-D-glucuronideGenerator
Luteolin 7-O-β-D-glucuronideGenerator
Luteolin-7-glucuronideHMDB
Luteolin 7-glucuronideChEBI
Chemical FormulaC21H18O12
Average Molecular Mass462.360 g/mol
Monoisotopic Mass462.080 g/mol
CAS Registry Number29741-10-4
IUPAC Name(2S,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Nameluteolin 7-O-glucuronide
SMILESO[C@@H]1[C@@H](O)[C@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C(O)=C2)O[C@@H]([C@H]1O)C(O)=O
InChI IdentifierInChI=1S/C21H18O12/c22-9-2-1-7(3-10(9)23)13-6-12(25)15-11(24)4-8(5-14(15)32-13)31-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-24,26-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
InChI KeyVSUOKLTVXQRUSG-ZFORQUDYSA-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
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • 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
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility1.38 g/LALOGPS
logP1.22ALOGPS
logP0.46ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.74ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.91 m³·mol⁻¹ChemAxon
Polarizability42.87 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
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
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-a1ab194af3ec44e8608cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-01p9-0090800000-7a8025a006c228d7dd96Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-8d538b68e20ab56be747Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01p9-0090800000-1d69dbf4c423530040cfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-b93abd5ae07655721b4bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000i-0190000000-4e013df19881c514c9ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01pa-0190700000-157efa860f7333ed6f6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0190000000-9811749c38f2e0788085Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-1490000000-87057301c94005590cb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03y0-1251900000-9a2aad2d89b77e8a9e1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2291200000-a567f6d5a16cee65c58cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3290000000-7793a6181e6b56142a4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01p9-0090600000-19b1a8eac4408670b577Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0020-0090000000-c3ca49aca7adc52662acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0020-0090000000-68306dd5c050e9a6b46bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p9-0090400000-9228c9224a8a67e29f26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-ad6070afb384abda8f3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-ad6070afb384abda8f3bSpectrum
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 IDHMDB0240541
FooDB IDFDB017828
Phenol Explorer IDNot Available
KNApSAcK IDC00004268
BiGG IDNot Available
BioCyc IDLUTEOLIN-7-O-BETA-D-GLUCURONIDE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4444211
ChEBI ID18128
PubChem Compound ID5280601
Kegg Compound IDC03515
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12088434
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1620743
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=7766058