Kaempferol 3-rhamno-glucoside (CHEM025619)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:30:32 UTC
Update Date2016-11-09 01:18:07 UTC
Accession NumberCHEM025619
Identification
Common NameKaempferol 3-rhamno-glucoside
ClassSmall Molecule
DescriptionA kaempferol O-glucoside that is kaempferol attached to a rutinosyl [6-deoxy-alpha-L-mannosyl-(1->6)-beta-D-glucosyl] residue at position 3 via a glycosidic linkage. It has been isolated from the leaves of Solanum campaniforme.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
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-alpha-L-rhamanopyranosyl-(1'''-6'')-beta-D-glucopyranosideMeSH
Kaempferol-3-O-rhamanopyranosyl-(1'''-6'')-glucopyranosideMeSH
Chemical FormulaC27H30O15
Average Molecular Mass594.518 g/mol
Monoisotopic Mass594.158 g/mol
CAS Registry NumberNot Available
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
Traditional 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}chromen-4-one
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
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
Chemical Taxonomy
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
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 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0019021000-2120b36108b3049a3b92Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0udi-0019021000-2120b36108b3049a3b92Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0019021000-2120b36108b3049a3b92Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 41V, positivesplash10-000j-0090500000-0b9ee5471da52c9d0751Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 41V, positivesplash10-000i-0090200000-85829de197e79ceb5365Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190170000-cbbfa6e6436ab3114340Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190100000-272d239a863d3824e317Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1590000000-35da131ffc18abfc9195Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-3480390000-54ce8f0710ea31445452Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2490010000-30e0c0dbb1b7f96b040aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2590000000-5d4a7819c8879a7061b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000090000-aa4f39d4b1dddc52ff15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0050090000-788103100cf62fddb95cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090000000-4ae644988c454965659aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090020000-169ebb44d50a4124cb0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-0090090000-6c63218d27f624537079Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-03ec6f5113b2bb58d5cfSpectrum
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 IDHMDB0302426
FooDB IDFDB005905
Phenol Explorer IDNot Available
KNApSAcK IDC00005169
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4477257
ChEBI ID69657
PubChem Compound ID5318767
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21962208
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22677447
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23912804
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24123927
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24128471