Kaempferol 3-O-feruloyl-caffeoyl-sophoroside 7-O-glucoside (CHEM022918)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:44:06 UTC
Update Date2016-11-09 01:17:36 UTC
Accession NumberCHEM022918
Identification
Common NameKaempferol 3-O-feruloyl-caffeoyl-sophoroside 7-O-glucoside
ClassSmall Molecule
DescriptionKaempferol 3-O-feruloyl-caffeoyl-sophoroside 7-O-glucoside is a polyphenol compound found in foods of plant origin (PMID: 20428313)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
[(2R,3S,4S,5R,6S)-6-{[(2R,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acidHMDB
Chemical FormulaC52H54O27
Average Molecular Mass1110.969 g/mol
Monoisotopic Mass1110.285 g/mol
CAS Registry NumberNot Available
IUPAC Name[(2R,3S,4S,5R,6S)-6-{[(2R,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-3-yl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Traditional Name[(2R,3S,4S,5R,6S)-6-{[(2R,3R,4S,5S,6R)-6-({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-3-yl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
SMILESCOC1=CC(\C=C\C(=O)OC[C@H]2O[C@@H](O[C@H]3[C@@H](OC4=C(OC5=CC(O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)=CC(O)=C5C4=O)C4=CC=C(O)C=C4)O[C@H](COC(=O)\C=C\C4=CC=C(O)C(O)=C4)[C@@H](O)[C@@H]3O)[C@H](O)[C@@H](O)[C@@H]2O)=CC=C1O
InChI IdentifierInChI=1S/C52H54O27/c1-70-30-15-22(3-11-27(30)56)5-13-36(60)71-19-33-39(62)43(66)46(69)51(76-33)79-49-44(67)40(63)34(20-72-35(59)12-4-21-2-10-26(55)28(57)14-21)77-52(49)78-48-41(64)37-29(58)16-25(73-50-45(68)42(65)38(61)32(18-53)75-50)17-31(37)74-47(48)23-6-8-24(54)9-7-23/h2-17,32-34,38-40,42-46,49-58,61-63,65-69H,18-20H2,1H3/b12-4+,13-5+/t32-,33-,34-,38-,39-,40-,42+,43+,44+,45-,46-,49-,50-,51+,52-/m1/s1
InChI KeyUICLSFURXKZJDP-XVAZHBMXSA-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
  • Flavonoid-7-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • Chromone
  • Disaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Catechol
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Benzenoid
  • Vinylogous acid
  • Enoate ester
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.32 g/LALOGPS
logP2.17ALOGPS
logP1.12ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)8.06ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area426.73 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity263.39 m³·mol⁻¹ChemAxon
Polarizability105.76 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0535-5921822806-0475b49312877fb723a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06rj-1791626602-a707bb2736cf710f4f5eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-1691215100-28de8d64fc3d62e4ebf7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004l-1901000101-acceba58dec4b5ea279aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-1901100100-e8fa2c14a346d09d8431Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-1932102001-99d44a0c3e0a543589deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-aa066ee31132143cf528Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0900000005-2ca37a5497e3095b61d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0100000009-611763431da33ec60c3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0400000009-b4d284eff2386364b34bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0100000009-52a38c6d271eb7951284Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-0000000009-9adf6c300f605e7b43b5Spectrum
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 IDHMDB0029266
FooDB IDFDB000182
Phenol Explorer ID344
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776753
ChEBI IDNot Available
PubChem Compound ID131750835
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.