Kaempferol 3-O-sinapoyl-caffeoyl-sophoroside 7-O-glucoside (CHEM022917)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:44:04 UTC
Update Date2016-11-09 01:17:36 UTC
Accession NumberCHEM022917
Identification
Common NameKaempferol 3-O-sinapoyl-caffeoyl-sophoroside 7-O-glucoside
ClassSmall Molecule
DescriptionKaempferol 3-O-sinapoyl-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-3,5-dimethoxyphenyl)prop-2-enoic acidHMDB
Chemical FormulaC53H56O28
Average Molecular Mass1140.995 g/mol
Monoisotopic Mass1140.296 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-3,5-dimethoxyphenyl)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-3,5-dimethoxyphenyl)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(OC)=C1O
InChI IdentifierInChI=1S/C53H56O28/c1-71-30-14-22(15-31(72-2)38(30)61)5-12-36(60)73-19-33-40(63)44(67)47(70)52(78-33)81-50-45(68)41(64)34(20-74-35(59)11-4-21-3-10-26(56)27(57)13-21)79-53(50)80-49-42(65)37-28(58)16-25(75-51-46(69)43(66)39(62)32(18-54)77-51)17-29(37)76-48(49)23-6-8-24(55)9-7-23/h3-17,32-34,39-41,43-47,50-58,61-64,66-70H,18-20H2,1-2H3/b11-4+,12-5+/t32-,33-,34-,39-,40-,41-,43+,44+,45+,46-,47-,50-,51-,52+,53-/m1/s1
InChI KeyGINCECVAGAWZPZ-LXWFTQFXSA-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
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Disaccharide
  • Glycosyl compound
  • Chromone
  • O-glycosyl compound
  • Methoxyphenol
  • Benzopyran
  • 1-benzopyran
  • Dimethoxybenzene
  • M-dimethoxybenzene
  • Methoxybenzene
  • Phenoxy compound
  • Styrene
  • Anisole
  • Catechol
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Pyran
  • Oxane
  • Fatty acyl
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Oxacycle
  • Acetal
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • 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
logP0.96ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.04ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area435.96 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity269.86 m³·mol⁻¹ChemAxon
Polarizability108.7 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, Positivesplash10-0aba-0951621604-b281391e016a47dc92ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0590525501-882fc0f00f5b3c76adedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-0591214100-1f44ee91a076b415c595Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-076r-0952101101-9a7aa096ad0f832c3fe9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-0952200100-a126207077f514247d4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-009i-1593102000-443228e71cbd73810739Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0400000009-4459249acf2b68f1b288Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0100000009-9cabd8eb28199b70679eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0000000009-5a969c7d5ecdac0963e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-ed8bffbd4ab76865572fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-0900000005-cba10b4ecc793e9f5e41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0100000009-35ce8506cb459bca1674Spectrum
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 IDHMDB0029265
FooDB IDFDB000181
Phenol Explorer ID343
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30776750
ChEBI IDNot Available
PubChem Compound ID131750834
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.