Kaempferol 3-(p-coumaroyl-glucoside) (CHEM026359)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:56:39 UTC
Update Date2016-11-09 01:18:15 UTC
Accession NumberCHEM026359
Identification
Common NameKaempferol 3-(p-coumaroyl-glucoside)
ClassSmall Molecule
DescriptionA glycosyloxyflavone that is kaempferol attached to a 6-O--beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Kaempferol-3-O-beta-D-(6''-(e)-p-coumaroyl)-glucopyranosideChEBI
Kaempferol-3-O-b-D-(6''-(e)-p-coumaroyl)-glucopyranosideGenerator
Kaempferol-3-O-β-D-(6''-(e)-p-coumaroyl)-glucopyranosideGenerator
Kaempferol 3-O-p-coumaroylglucosidePhytoBank
Astragalin-6"-trans-p-coumaratePhytoBank
Astragalin-6″-trans-p-coumaratePhytoBank
Kaempferol 3-O-(6''-O-p-coumaroyl)glucosidePhytoBank
Kaempferol 3-O-(6’’-O-p-coumaroyl)glucosidePhytoBank
Kaempferol 3-O-(6''-trans-p-coumaroyl)-beta-D-glucopyranosidePhytoBank
Kaempferol 3-O-(6''-trans-p-coumaroyl)-β-D-glucopyranosidePhytoBank
Kaempferol 3-O-(6’’-trans-p-coumaroyl)-β-D-glucopyranosidePhytoBank
Kaempferol 3-O-[6''-O-(E)-p-coumaroyl]-beta-D-glucopyranosidePhytoBank
Kaempferol 3-O-[6''-O-(E)-p-coumaroyl]-β-D-glucopyranosidePhytoBank
Kaempferol 3-O-[6’’-O-(E)-p-coumaroyl]-β-D-glucopyranosidePhytoBank
Kaempferol 3-O-[6''-O-(trans-p-coumaroyl)]-beta-D-glucopyranosidePhytoBank
Kaempferol 3-O-[6''-O-(trans-p-coumaroyl)]-β-D-glucopyranosidePhytoBank
Kaempferol 3-O-[6’’-O-(trans-p-coumaroyl)]-β-D-glucopyranosidePhytoBank
Kaempferol 3-O-beta-D-(6-O-trans-4-hydroxycinnamoyl)glucopyranosidePhytoBank
Kaempferol 3-O-β-D-(6-O-trans-4-hydroxycinnamoyl)glucopyranosidePhytoBank
Kaempferol 3-O-beta-D-(6-O-trans-p-coumaroyl)glucopyranosidePhytoBank
Kaempferol 3-O-β-D-(6-O-trans-p-coumaroyl)glucopyranosidePhytoBank
Kaempferol 3-O-beta-D-(6''-E-p-coumaroyl)glucopyranosidePhytoBank
Kaempferol 3-O-β-D-(6''-E-p-coumaroyl)glucopyranosidePhytoBank
Kaempferol 3-O-β-D-(6’’-E-p-coumaroyl)glucopyranosidePhytoBank
Kaempferol 3-O-beta-D-(6''-O-p-coumaryl)glycosidePhytoBank
Kaempferol 3-O-β-D-(6''-O-p-coumaryl)glycosidePhytoBank
Kaempferol 3-O-β-D-(6’’-O-p-coumaryl)glycosidePhytoBank
Kaempferol 3-O-beta-D-6-O-(p-hydroxycinnamoyl)glucopyranosidePhytoBank
Kaempferol 3-O-β-D-6-O-(p-hydroxycinnamoyl)glucopyranosidePhytoBank
Kaempferol 3-beta-D-(6-O-trans-p-coumaryl)glucopyranosidePhytoBank
Kaempferol 3-β-D-(6-O-trans-p-coumaryl)glucopyranosidePhytoBank
Kaempferol-3-O-beta-D-(6''-O-(E)-p-coumaroyl)glucopyranosidePhytoBank
Kaempferol-3-O-β-D-(6''-O-(E)-p-coumaroyl)glucopyranosidePhytoBank
Kaempferol-3-O-β-D-(6’’-O-(E)-p-coumaroyl)glucopyranosidePhytoBank
Kaempferol-3-O-beta-D-(6''-trans-p-coumaroyl) glucopyranosidePhytoBank
Kaempferol-3-O-β-D-(6''-trans-p-coumaroyl) glucopyranosidePhytoBank
Kaempferol-3-O-β-D-(6’’-trans-p-coumaroyl) glucopyranosidePhytoBank
Potengriffioside APhytoBank
trans-TilirosidePhytoBank
Kaempferol-3-O-beta-D-(6''-O-p-coumaryl)glycosidePhytoBank
Kaempferol-3-O-β-D-(6''-O-p-coumaryl)glycosidePhytoBank
Kaempferol-3-O-β-D-(6’’-O-p-coumaryl)glycosidePhytoBank
Kaempferol 3-beta-D-(6"-O-p-coumaroyl) glucosidePhytoBank
Kaempferol 3-β-D-(6"-O-p-coumaroyl) glucosidePhytoBank
Kaempferol 3-β-D-(6″-O-p-coumaroyl) glucosidePhytoBank
Tribuloside APhytoBank
Chemical FormulaC30H26O13
Average Molecular Mass594.520 g/mol
Monoisotopic Mass594.137 g/mol
CAS Registry NumberNot Available
IUPAC Name[(2R,3S,4S,5R,6S)-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
Traditional Name[(2R,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate
SMILESO[C@@H]1[C@@H](COC(=O)\C=C\C2=CC=C(O)C=C2)O[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@H]1O
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+/t21-,24-,26+,27-,30+/m1/s1
InChI KeyDVGGLGXQSFURLP-VWMSDXGPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid 3-O-p-coumaroyl glycosides
Alternative Parents
Substituents
  • Flavonoid 3-o-6-p-coumaroyl-glycoside
  • Flavonoid-3-o-glycoside
  • Flavone
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Coumaric acid ester
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • Chromone
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Styrene
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Monosaccharide
  • Oxane
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen 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 Solubility0.18 g/LALOGPS
logP2.97ALOGPS
logP2.89ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
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
Polarizability58.65 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0000090000-c4777c3f691ad06be46eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0000090000-c4777c3f691ad06be46eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-004i-0000090000-c4777c3f691ad06be46eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0019-0090000000-ad81e03cb2a2ff5bdcdfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0490350000-c0911ae64c00bc067138Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0290000000-f9ea658e54cfef4e8836Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-0890000000-86dd969d4d72d7ed325bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01p5-0940140000-b9a14cb7eb5dcc60c4d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01pa-0960100000-e363837065830c134fd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-1970000000-f29307b10bfd0c35cf41Spectrum
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 IDHMDB0240322
FooDB IDFDB007335
Phenol Explorer IDNot Available
KNApSAcK IDC00034908
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID80944
PubChem Compound ID5320686
Kegg Compound IDC17140
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17504571
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24443810
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25348942