Record Information
Version1.0
Creation date2010-04-08 22:04:29 UTC
Update date2018-01-25 19:27:13 UTC
Primary IDFDB000215
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameKaempferol 3-O-rhamnosyl-rhamnosyl-glucoside
DescriptionKaempferol 3-o-rhamnosyl-rhamnosyl-glucoside is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-o-rhamnosyl-rhamnosyl-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 3-o-rhamnosyl-rhamnosyl-glucoside can be found in a number of food items such as rosemary, common thyme, capers, and common sage, which makes kaempferol 3-o-rhamnosyl-rhamnosyl-glucoside a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility6.58 g/LALOGPS
logP-0.12ALOGPS
logP-1.3ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area304.21 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity169.03 m³·mol⁻¹ChemAxon
Polarizability71.12 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC33H40O19
IUPAC name3-{[(2S,3R,4S,5S,6R)-6-({[(2R,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
InChI IdentifierInChI=1S/C33H40O19/c1-10-19(37)23(41)26(44)31(47-10)52-30-25(43)20(38)11(2)48-33(30)46-9-17-21(39)24(42)27(45)32(50-17)51-29-22(40)18-15(36)7-14(35)8-16(18)49-28(29)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-27,30-39,41-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21+,23+,24-,25+,26+,27+,30+,31-,32-,33+/m0/s1
InChI KeyWQRYALSJYYLFRY-YBDKOUSASA-N
Isomeric SMILESC[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=CC(O)=CC(O)=C4C3=O)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H]1O
Average Molecular Weight740.6593
Monoisotopic Molecular Weight740.216379098
Classification
DescriptionThis compound belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Oligosaccharide
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • Flavone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Resorcinol
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
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
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002s-0290170500-58166586204e334bf850View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190120000-a26f2deb5d8b8bb37a41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0591010000-a91c7badf6f031c97c67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2492351600-f75da37f5999ec9efd8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1690020100-703ad5cf64fd69b85f22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3590000000-7221740d6cb2939bc677View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID385
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
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
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.