Record Information
Version1.0
Creation date2010-04-08 22:12:52 UTC
Update date2019-11-26 03:14:19 UTC
Primary IDFDB017159
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-galactoside
DescriptionCyanidin 3-galactoside, also known as idaein, belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position. Cyanidin 3-galactoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Cyanidin 3-galactoside is found, on average, in the highest concentration in a few different foods, such as black chokeberries, lingonberries, and bilberries and in a lower concentration in american cranberries, lowbush blueberries, and highbush blueberries. Cyanidin 3-galactoside has also been detected, but not quantified in, several different foods, such as summer grapes, common grapes, blackcurrants, red raspberries, and black elderberries. This could make cyanidin 3-galactoside a potential biomarker for the consumption of these foods.
CAS Number27661-36-5
Structure
Thumb
Synonyms
SynonymSource
Cyanidin 3-O-galactosideChEBI
Cyanidin 3-O-beta-D-galactosideKegg
Cyanidin 3-O-b-D-galactosideGenerator
Cyanidin 3-O-β-D-galactosideGenerator
Cyanidin 3-O-beta-D-galactopyranosideHMDB
IdaeinHMDB
IdeinHMDB
Cy3-galMeSH
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-chromeniumyl beta-D-galactopyranoside chlorideMeSH
Cyanidin 3-galactosideMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.6 g/LALOGPS
logP0.98ALOGPS
logP0.39ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area193.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity116.26 m³·mol⁻¹ChemAxon
Polarizability43.04 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H21O11
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C21H20O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-6-10-12(25)4-9(23)5-14(10)30-20(15)8-1-2-11(24)13(26)3-8/h1-6,16-19,21-22,27-29H,7H2,(H3-,23,24,25,26)/p+1/t16-,17+,18+,19-,21-/m1/s1
InChI KeyRKWHWFONKJEUEF-WVXKDWSHSA-O
Isomeric SMILESOC[C@H]1O[C@@H](OC2=CC3=C(C=C(O)C=C3O)[O+]=C2C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@H]1O
Average Molecular Weight449.3848
Monoisotopic Molecular Weight449.108386514
Classification
Description belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin-3-O-glycosides
Alternative Parents
Substituents
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Anthocyanidin
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.13%; H 4.71%; O 39.16%DFC
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-9613500000-4ecd805029dccd975fedJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-6620019000-8d5ae8efad054c2ab4aaJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001j-0190300000-066e4efe2ad20a1bf618JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0170-0982400000-096c82f5e6fc50eb3a1fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0090000000-a98c476e0842377a0be6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014m-0950000000-b95724097dd0841523e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001j-0090300000-4118b3f51610a89ec6bdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090100000-34fecd8af8ace7f092c0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-fc644549112cedb4265fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090100000-0407b88d0009c9229fdfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0100900000-66702edb3ac17b9bcd2fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1300900000-733c7273cc2b516ea7fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-6910000000-5dad4cb81406b2f0a241JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2300900000-5d1238580ea9280c8190JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-6800900000-f91084c3d800ee4ef894JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9300000000-1ee778ebb732d2be0d87JSpectraViewer
ChemSpider ID390306
ChEMBL IDCHEMBL1197952
KEGG Compound IDC08647
Pubchem Compound ID441699
Pubchem Substance IDNot Available
ChEBI ID27475
Phenol-Explorer ID8
DrugBank IDNot Available
HMDB IDHMDB37977
CRC / DFC (Dictionary of Food Compounds) IDODW39-O:KWM68-J
EAFUS IDNot Available
Dr. Duke IDCYANIDIN-3-O-GALACTOSIDE|CYANIDIN-3-O-BETA-GALACTOSIDE|3-BETA-D-GALACTOSIDYL-CYANIDIN|CYANIDIN-3-GALACTOSIDE|IDAEIN
BIGG IDNot Available
KNApSAcK IDC00006652
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 ID8
Duplicate IDSNot Available
Old DFC IDSCMQ73-Z:KWM68-J
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti capillary-fragilityDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
pigment26130 An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— 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.