Kaempferol 3-gentiobioside (CHEM031080)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:22:39 UTC
Update Date2016-11-09 01:19:12 UTC
Accession NumberCHEM031080
Identification
Common NameKaempferol 3-gentiobioside
ClassSmall Molecule
DescriptionA kaempferol O-glucoside in which the hydroxy hydrogen at position 3 of kaempferol has been replaced by a gentiobiosyl group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-beta-D-glucosyl-beta-D-glucosideChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosideChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl beta-D-glucosyl-(1->6)-beta-D-glucosideChEBI
Kaempferol 3-gentiobiosideChEBI
Kaempferol 3-O-beta-gentiobiosideChEBI
Kaempferol 3-O-gentiobiosideChEBI
Kaempferol beta-D-glucopyranosyl-(1->6)-beta-D-glucopyranosideChEBI
Kaempferol beta-D-glucosyl-(1->6)-beta-D-glucosideChEBI
Kaempferol-3-gentiobiosideChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-b-D-glucosyl-b-D-glucosideGenerator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-β-D-glucosyl-β-D-glucosideGenerator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl b-D-glucopyranosyl-(1->6)-b-D-glucopyranosideGenerator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl β-D-glucopyranosyl-(1->6)-β-D-glucopyranosideGenerator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl b-D-glucosyl-(1->6)-b-D-glucosideGenerator
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl β-D-glucosyl-(1->6)-β-D-glucosideGenerator
Kaempferol 3-O-b-gentiobiosideGenerator
Kaempferol 3-O-β-gentiobiosideGenerator
Kaempferol b-D-glucopyranosyl-(1->6)-b-D-glucopyranosideGenerator
Kaempferol β-D-glucopyranosyl-(1->6)-β-D-glucopyranosideGenerator
Kaempferol b-D-glucosyl-(1->6)-b-D-glucosideGenerator
Kaempferol β-D-glucosyl-(1->6)-β-D-glucosideGenerator
Kaempferol 3-b-gentiobiosideGenerator
Kaempferol 3-β-gentiobiosideGenerator
Chemical FormulaC27H30O16
Average Molecular Mass610.518 g/mol
Monoisotopic Mass610.153 g/mol
CAS Registry Number22149-35-5
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-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,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one
SMILESOC[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/C27H30O16/c28-7-14-17(32)20(35)22(37)26(41-14)39-8-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-12(31)5-11(30)6-13(16)40-24(25)9-1-3-10(29)4-2-9/h1-6,14-15,17-18,20-23,26-33,35-38H,7-8H2/t14-,15-,17-,18-,20+,21+,22-,23-,26-,27+/m1/s1
InChI KeyBITPRCODIALMOV-DEFKTLOSSA-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
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • Disaccharide
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Monocyclic benzene moiety
  • Oxane
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Polyol
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility4.19 g/LALOGPS
logP-0.55ALOGPS
logP-1.6ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)6.43ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area265.52 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity139.71 m³·mol⁻¹ChemAxon
Polarizability57.53 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01pc-0190143000-4d3ca8696a9ca5881294Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190100000-42defd97e04f0701564aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1490000000-65b3b830915595810158Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-3590336000-d41f3b0fd0452e124092Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2590010000-077bd447d607677bcf32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2490000000-0a84a391693fa4be4e1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090002000-ad3a3f348911592bbc78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e0-0090009000-44f74805e800438ba137Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-03ec6f5113b2bb58d5cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000009000-ca3de2148f610274d38fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0050009000-e16b0b6b52763e1336e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0090000000-a468087f26d50558521aSpectrum
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 IDHMDB0303606
FooDB IDFDB016664
Phenol Explorer IDNot Available
KNApSAcK IDC00005166
BiGG IDNot Available
BioCyc IDCPD-14847
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8136119
ChEBI ID136785
PubChem Compound IDNot Available
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=10854741
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11725550
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12837355
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=12875244
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17420179
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18825536
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18991205
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19177235
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23137344
10.