Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2020-02-24 19:10:33 UTC
Primary IDFDB002603
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-glucoside
DescriptionCyanidin 3-glucoside, also known as asterin? or chrysontemin, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Cyanidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Cyanidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as black elderberries, rubus (blackberry, raspberry), and bilberries and in a lower concentration in peach (var.), common grapes, and american cranberries. Cyanidin 3-glucoside has also been detected, but not quantified in, several different foods, such as quinoa, rabbiteye blueberries, cottonseeds, fruits, and garden onions. This could make cyanidin 3-glucoside a potential biomarker for the consumption of these foods.
CAS Number7084-24-4
Structure
Thumb
Synonyms
SynonymSource
Cyanidin 3-O-glucosideChEBI
ChrysonteminHMDB
Cyanidin 3-monoglucosideHMDB
Cyanidin 3-O-beta-D-glucosideHMDB, KEGG
Cyanidol 3-glucosideHMDB
GlucocyanidinHMDB
KuromamineHMDB
Cyanidin 3-O-b-D-glucosideGenerator
Cyanidin 3-O-β-D-glucosideGenerator
Cyanidin 3-O-glucopyranosideMeSH
Cyanidin 3-O-beta-D-glucopyranosideMeSH
2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyryliumHMDB
2-(3,4-Dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-1-benzopyryliumHMDB
3-(beta-D-Glucopyranosyloxy)-3',4',5,7-tetrahydroxyflavylium chlorideHMDB
3-(β-D-Glucopyranosyloxy)-3',4',5,7-tetrahydroxyflavylium chlorideHMDB
3-(β-D-Glucopyranosyloxy)-3’,4’,5,7-tetrahydroxyflavylium chlorideHMDB
3-O-(beta-D-Glucopyranosyl)cyanidinHMDB
3-O-(β-D-Glucopyranosyl)cyanidinHMDB
AsterinHMDB
ChrysantheminHMDB
ChrysantheninHMDB
Cyanidin 3-O-beta-glucopyranosideHMDB
Cyanidin 3-O-beta-glucosideHMDB
Cyanidin 3-O-glucoside chlorideHMDB
Cyanidin 3-O-β-D-glucopyranosideHMDB
Cyanidin 3-O-β-glucopyranosideHMDB
Cyanidin 3-O-β-glucosideHMDB
Cyanidin 3-beta-D-O-glucosideHMDB
Cyanidin 3-beta-D-glucopyranosideHMDB
Cyanidin 3-beta-O-glucosideHMDB
Cyanidin 3-beta-glucopyranosideHMDB
Cyanidin 3-beta-glucosideHMDB
Cyanidin 3-beta-glucoside cationHMDB
Cyanidin 3-glucosideHMDB
Cyanidin 3-glucoside chlorideHMDB
Cyanidin 3-β-D-O-glucosideHMDB
Cyanidin 3-β-D-glucopyranosideHMDB
Cyanidin 3-β-O-glucosideHMDB
Cyanidin 3-β-glucopyranosideHMDB
Cyanidin 3-β-glucosideHMDB
Cyanidin 3-β-glucoside cationHMDB
KuromaninHMDB
KuromanineHMDB
Asterin?db_source
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 Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area193.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity116.26 m³·mol⁻¹ChemAxon
Polarizability43.14 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,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1lambda4-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-GQUPQBGVSA-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 pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentPyranones and derivatives
Alternative Parents
Substituents
  • Pyranone
  • Heteroaromatic compound
  • Secondary alcohol
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Foods

Beverages:

Fruits and vegetables:

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 , negativesplash10-0012-0190300000-fa49c39b10bc818caf38JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0170-0982400000-bf6abe51e9ef29f65fe0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001r-0190000000-1d3575fd8a5bad57646cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0940000000-688e280b84a3b096281cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001s-0090200000-abde441c456e0554b97bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090100000-d8c555166d10dec1fb48JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-0ee5168148d1f43f98b9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090100000-1dc5f0ee658f46d936dfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090200000-d45f62202546a09960c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0190000000-86b08922db000308f1b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-0890000000-f54a34d80fd4bb859a26JSpectraViewer
ChemSpider ID3679222
ChEMBL IDNot Available
KEGG Compound IDC08604
Pubchem Compound ID4481259
Pubchem Substance IDNot Available
ChEBI ID28426
Phenol-Explorer ID9
DrugBank IDNot Available
HMDB IDHMDB30684
CRC / DFC (Dictionary of Food Compounds) IDODW39-O:CMQ75-B
EAFUS IDNot Available
Dr. Duke IDCYANIDIN-3-O-GLUCOSIDE|CYANIDIN-3-O-BETA-D-GLUCOSIDE|CYANIDIN-3-MONOGLUCOSIDE|CYANIDIN-3-GLUCOSIDE|CHRYSANTHEMIN
BIGG IDNot Available
KNApSAcK IDC00002374
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 ID9
Duplicate IDS
Old DFC IDSCMQ73-Z:CMQ75-B
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti diabetic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti hyperglycemicDUKE
anti hyperinsulinemicDUKE
anti hyperleptinemicDUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti obesity52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.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
anti radicularDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cyclooxygenase-1 inhibitor50630 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
insulinogenicDUKE
larvistatDUKE
lipolyticDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
pigment26130 An endogenous molecular entity that results in a colour of an organism as the consequence of the selective absorption of light.DUKE
secretogogueDUKE
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.