Record Information
Creation date2010-04-08 22:04:27 UTC
Update date2019-11-26 02:54:32 UTC
Primary IDFDB000139
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLuteolin 7-malonylglucoside
DescriptionLuteolin 7-malonylglucoside, also known as luteolin 7-O-B-D-(6''-O-malonyl) glucopyranoside, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Luteolin 7-malonylglucoside is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Luteolin 7-malonylglucoside can be found in celery leaves, globe artichoke, and wild celery, which makes luteolin 7-malonylglucoside a potential biomarker for the consumption of these food products.
CAS Number98767-38-5
Luteolin 7-O-(6''-malonylglucoside)ChEBI
Luteolin 7-O-(6-malonyl-beta-D-glucoside)ChEBI
Luteolin 7-O-beta-D-(6''-O-malonyl) glucopyranosideChEBI
Luteolin 7-O-(6-malonyl-b-D-glucoside)Generator
Luteolin 7-O-(6-malonyl-β-D-glucoside)Generator
Luteolin 7-O-b-D-(6''-O-malonyl) glucopyranosideGenerator
Luteolin 7-O-β-D-(6''-O-malonyl) glucopyranosideGenerator
Luteolin 7-malonylglucosidemanual
Luteolin 7-O-malonyl-glucosidedb_source
Predicted Properties
Water Solubility0.64 g/LALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area229.74 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity122.53 m³·mol⁻¹ChemAxon
Polarizability49.8 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC24H22O14
IUPAC name3-{[(2R,3S,4S,5R,6S)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3-oxopropanoic acid
InChI IdentifierInChI=1S/C24H22O14/c25-11-2-1-9(3-12(11)26)15-6-14(28)20-13(27)4-10(5-16(20)37-15)36-24-23(34)22(33)21(32)17(38-24)8-35-19(31)7-18(29)30/h1-6,17,21-27,32-34H,7-8H2,(H,29,30)/t17-,21-,22+,23-,24-/m1/s1
Isomeric SMILESO[C@H]1[C@H](O)[C@@H](COC(=O)CC(O)=O)O[C@@H](OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C(O)=C2)[C@@H]1O
Average Molecular Weight534.4231
Monoisotopic Molecular Weight534.100955412
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
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glucuronides
Alternative Parents
  • Flavonoid-7-o-glucuronide
  • Flavonoid-7-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Beta-hydroxy acid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-2090450000-df3707caed69bdcdb17dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1090100000-0e17d78600d9ec8305cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-2390000000-9e9f886f0dfe1a81d035JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f8i-9870550000-2c8c4fefd415a91f877eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-7590200000-8780650492c00887e8daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kui-5490000000-e411ce222b97245ed2e7JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID253
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.