Record Information
Version1.0
Creation date2010-04-08 22:12:28 UTC
Update date2020-02-24 19:11:06 UTC
Primary IDFDB016491
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameKaempferol 3-rhamnoside
Description5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one 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. 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one can be found in a number of food items such as endive, linden, peach, and ginkgo nuts, which makes 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one a potential biomarker for the consumption of these food products.
CAS Number482-39-3
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.55 g/LALOGPS
logP1.48ALOGPS
logP1.21ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.37ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.75 m³·mol⁻¹ChemAxon
Polarizability41.48 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H20O10
IUPAC name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one
InChI IdentifierInChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3
InChI KeySOSLMHZOJATCCP-UHFFFAOYSA-N
Isomeric SMILESCC1OC(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)C(O)C(O)C1O
Average Molecular Weight432.3775
Monoisotopic Molecular Weight432.10564686
Classification
Description Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassPyranocoumarins
Direct ParentAngular pyranocoumarins
Alternative Parents
Substituents
  • Angular pyranocoumarin
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Ketone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alkyl halide
  • Alkyl chloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSKaempferol 3-rhamnoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9400018000-17fb5e3e35e98d41d031Spectrum
Predicted GC-MSKaempferol 3-rhamnoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0cki-9201300000-830960f1817f19cf7853Spectrum
Predicted GC-MSKaempferol 3-rhamnoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSKaempferol 3-rhamnoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSKaempferol 3-rhamnoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSKaempferol 3-rhamnoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000900000-05005dc7edc5489a012d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-0090000000-66802ceba8ff6e82f6bc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0090000000-cd6d7eae4e9ed074e6202021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001r-0090000000-0d12f6be6ca409382aa42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-0050900000-75b20c99cef7babe27f92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001r-0090300000-6afda67c541e439ff5d62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a5i-0090000000-bbffde337aa8d734893a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-001r-0090100000-6b3503dac56edc87bac82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Negativesplash10-0a6r-0090000000-82affed668343724370d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-9a0204794defdae7c1ef2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0030900000-ef6e5b8295cce8075fce2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-056r-0390000000-ccd5d24e81c6cb73b71b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-9873ad61c22ae88b9cf92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-06e62a7cd63ef54fd9b32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0030900000-b81e162465933abf92a12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001r-0090300000-3fbb6905edef9aacf72a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a5i-0090000000-92d5ad1de2238e6d00572021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-056r-0390000000-5ca37fb6f63ba82a3cb62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0a5i-0090000000-cfb8e209438d0cc7c1bd2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0019-0090700000-6a6674a147995db64f792016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-5cd7eb12bd78c20461e92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05n0-3590000000-e32f2e9d84ac948e887c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-1052900000-c28b8a434bdd24381abd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1090100000-31fcccb7f766720b4f992016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2490000000-8ae352e37bd6e673e7222016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5316673
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID351
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDKRH61-U:KRH61-U
EAFUS IDNot Available
Dr. Duke IDAFZELIN|KAEMPFEROL-3-RHAMNOSIDE
BIGG IDNot Available
KNApSAcK IDC00005140
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 IDS
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).