Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2015-07-20 21:46:57 UTC
Primary IDFDB002603
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin 3-glucoside
DescriptionFound in many plants and fruits, e.g. cherries, olives and grapes
CAS Number7084-24-4
Structure
Thumb
Synonyms
SynonymSource
Cyanidin 3-O-glucosideChEBI
Cyanidin 3-O-beta-D-glucosideKegg
Cyanidin 3-O-b-D-glucosideGenerator
Cyanidin 3-O-β-D-glucosideGenerator
Asterin?HMDB
ChrysonteminHMDB
Cyanidin 3-monoglucosideHMDB
Cyanidol 3-glucosideHMDB
GlucocyanidinHMDB
KuromamineHMDB
Cyanidin 3-O-glucopyranosideMeSH
Cyanidin 3-O-beta-D-glucopyranosideMeSH
Chrysanthemindb_source
Cyanidin 3-glucosidedb_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 Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area193.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity116.26 m³·mol⁻¹ChemAxon
Polarizability43.05 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
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}-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-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 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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
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 Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-9613500000-4ecd805029dccd975fedView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0002-6620019000-8d5ae8efad054c2ab4aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0012-0190300000-fa49c39b10bc818caf38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0170-0982400000-bf6abe51e9ef29f65fe0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001r-0190000000-1d3575fd8a5bad57646cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0940000000-688e280b84a3b096281cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001s-0090200000-abde441c456e0554b97bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090100000-d8c555166d10dec1fb48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-0ee5168148d1f43f98b9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090100000-1dc5f0ee658f46d936dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090200000-d45f62202546a09960c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0190000000-86b08922db000308f1b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-0890000000-f54a34d80fd4bb859a26View in MoNA
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
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.