Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2019-11-27 17:06:43 UTC
Primary IDFDB002430
Secondary Accession Numbers
  • FDB020488
Chemical Information
FooDB Name6''-(4-Hydroxycinnamoyl)astragalin
DescriptionKaempferol 3-(6''-p-coumaroylgalactoside) is a member of the class of compounds known as flavonoid 3-o-p-coumaroyl glycosides. Flavonoid 3-o-p-coumaroyl glycosides are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. Kaempferol 3-(6''-p-coumaroylgalactoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Within the cell, kaempferol 3-(6''-p-coumaroylgalactoside) is primarily located in the membrane (predicted from logP).
CAS Number20316-62-5
Structure
Thumb
Synonyms
SynonymSource
Kaempferol 3-(6-P-coumaroylgalactoside)HMDB
(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoic acidGenerator
6''-(4-Hydroxycinnamoyl)astragalinmanual
6''-O-(4-Hydroxycinnamoyl)astragalinmanual
Potengriffioside abiospider
Tilirosidedb_source
Tribulosidebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP2.97ALOGPS
logP2.89ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area212.67 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity148.84 m³·mol⁻¹ChemAxon
Polarizability57.63 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H26O13
IUPAC name(6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
InChI IdentifierInChI=1S/C30H26O13/c31-16-6-1-14(2-7-16)3-10-22(35)40-13-21-24(36)26(38)27(39)30(42-21)43-29-25(37)23-19(34)11-18(33)12-20(23)41-28(29)15-4-8-17(32)9-5-15/h1-12,21,24,26-27,30-34,36,38-39H,13H2/b10-3+
InChI KeyDVGGLGXQSFURLP-XCVCLJGOSA-N
Isomeric SMILESOC1C(COC(=O)\C=C\C2=CC=C(O)C=C2)OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(O)C1O
Average Molecular Weight594.5196
Monoisotopic Molecular Weight594.137340918
Classification
Description belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassKavalactones
Sub ClassNot Available
Direct ParentKavalactones
Alternative Parents
Substituents
  • Kavalactone
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Dihydropyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Lactone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.61%; H 4.41%; O 34.98%DFC
Melting PointMp 269-271° (267-269°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]24D +69.9 (c, 0.1 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00mk-4983240000-99127f52bd6fe47f3408View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000b-3923203000-dc4ba29827e830ac19e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0490350000-c0911ae64c00bc067138View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0290000000-f9ea658e54cfef4e8836View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-0890000000-86dd969d4d72d7ed325bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01p5-0940140000-b9a14cb7eb5dcc60c4d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01pa-0960100000-e363837065830c134fd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-1970000000-f29307b10bfd0c35cf41View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5320686
Pubchem Substance IDNot Available
ChEBI ID604269
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDKRH29-Q:CLT15-R
EAFUS IDNot Available
Dr. Duke IDTILIROSIDE
BIGG IDNot Available
KNApSAcK IDC00005851
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
diaphoreticDUKE
protisticideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).