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
SynonymSource
Kaempferol-3-O-alpha-L-rhamnosideMeSH, HMDB
Kaempferol-3-rhamnosideMeSH, HMDB
Deacyl-SL0101MeSH, HMDB
3-O-a-L-Rhamnopyranosyloxy-4',5,7-trihydroxyflavonedb_source
3,4',5,7-Tetrahydroxyflavone-3-L-rhamnosidebiospider
Afzelindb_source
Afzelosidedb_source
Kaempferindb_source
Kaempferol 3-a-L-rhamnosidedb_source
kaempferol 3-O-alpha-L-rhamnopyranosidebiospider
kaempferol-3-O-alpha-L-rhamnosidebiospider
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 - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.34%; H 4.66%; O 37.00%DFC
Melting PointMp 172-174°DFC
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
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).DUKE
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
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).