Record Information
Version1.0
Creation date2010-04-08 22:06:17 UTC
Update date2019-11-26 03:00:04 UTC
Primary IDFDB004523
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameKaempferol 3-rhamno-glucoside
DescriptionKaempferol 3-rhamno-glucoside, also known as nicotiflorin or kaempferol 3-rutinoside, 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-rhamno-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 3-rhamno-glucoside can be found in ginkgo nuts and tea, which makes kaempferol 3-rhamno-glucoside a potential biomarker for the consumption of these food products.
CAS Number17650-84-9
Structure
Thumb
Synonyms
SynonymSource
3-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
Kaempferol 3-O-(6''-O-alpha-L-rhamnopyranosyl)-beta-D-glucopyranosideChEBI
Kaempferol-3-O-beta-rutinosideChEBI
NicotiflorinChEBI
3-((6-O-(6-Deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneGenerator
3-((6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl)oxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneGenerator
Kaempferol 3-O-(6''-O-a-L-rhamnopyranosyl)-b-D-glucopyranosideGenerator
Kaempferol 3-O-(6''-O-α-L-rhamnopyranosyl)-β-D-glucopyranosideGenerator
Kaempferol-3-O-b-rutinosideGenerator
Kaempferol-3-O-β-rutinosideGenerator
Kaempferol-3-O-rhamanopyranosyl-(1'''-6'')-glucopyranosideMeSH
Kaempferol-3-O-alpha-L-rhamanopyranosyl-(1'''-6'')-beta-D-glucopyranosideMeSH
Predicted Properties
PropertyValueSource
Water Solubility3.07 g/LALOGPS
logP0.07ALOGPS
logP-0.57ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area245.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity138.16 m³·mol⁻¹ChemAxon
Polarizability56.68 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H30O15
IUPAC name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
InChI IdentifierInChI=1S/C27H30O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-18,20-23,26-32,34-37H,8H2,1H3/t9-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
InChI KeyRTATXGUCZHCSNG-QHWHWDPRSA-N
Isomeric SMILESC[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(OC4=C(C(O)=CC(O)=C4)C3=O)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O
Average Molecular Weight594.5181
Monoisotopic Molecular Weight594.15847029
Classification
Description 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
  • Flavonoid-3-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Oxane
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Organic oxygen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
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 KeyView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0019021000-2120b36108b3049a3b92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0udi-0019021000-2120b36108b3049a3b92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0019021000-2120b36108b3049a3b92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 41V, positivesplash10-000j-0090500000-0b9ee5471da52c9d0751JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 41V, positivesplash10-000i-0090200000-85829de197e79ceb5365JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190170000-cbbfa6e6436ab3114340JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190100000-272d239a863d3824e317JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1590000000-35da131ffc18abfc9195JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-3480390000-54ce8f0710ea31445452JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2490010000-30e0c0dbb1b7f96b040aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2590000000-5d4a7819c8879a7061b0JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDKAEMPFEROL-3-RHAMNOGLUCOSIDE
BIGG IDNot Available
KNApSAcK IDNot Available
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 IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cholereticDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
purgative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.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— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).