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Showing Compound Cyanidin (FDB002602)

Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2020-02-24 19:11:05 UTC
Primary IDFDB002602
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyanidin
DescriptionCyanidin, also known as cyanidol or cyanidin chloride, belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton. Thus, cyanidin is considered to be a flavonoid lipid molecule. Cyanidin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cyanidin is found, on average, in the highest concentration within a few different foods, such as black raspberries, elderberries, and black chokeberries and in a lower concentration in lingonberries, pistachio, and cloudberries. Cyanidin has also been detected, but not quantified in, several different foods, such as small-leaf lindens, common thymes, lichee, soy beans, and cocoa beans. This could make cyanidin a potential biomarker for the consumption of these foods.
CAS Number528-58-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-1-benzopyryliumChEBI
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxychromenyliumChEBI
3,3',4',5,7-PentahydroxyflavyliumChEBI
3,5,7,3',4'-PentahydroxyflavyliumChEBI
CyanidineChEBI
CyanidolChEBI
3,3',4',5,7-Pentahydroxyflavylium chlorideKEGG
Chlorure de 3,3',4',5,7-pentahydroxyflavyliumKEGG
3,3',4',5,7-PentahydroxyflavyliumchloridKEGG
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-1-benzopyrylium chlorideKEGG
3,3',4',5,7-Pentahydroxy-2-phenylbenzopyrylium chlorideKEGG
Cyanidin chlorideKEGG
Cyanidol chlorideKEGG
IdB 1027KEGG
Cyanidin ionMeSH
1-Benzopyrylium, 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-, chlorideMeSH
2-(3,4-Dihydroxyphenyl) chromenylium-3,5,7-triolMeSH
Flavylium, 3,3',4',5,7-pentahydroxy-, chlorideMeSH
1-Benzopyrylium, 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-, chloride (1:1)MeSH
Cyanidin cationMeSH
3,5,7,3’,4’-PentahydroxyflavyliumHMDB
CyanidinHMDB
1-Benzopyrylium, 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-biospider
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-1-benzopyrylium(1+), 9CIdb_source
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromenyliumbiospider
Cyanidol (6CI)manual
Flavylium, 3,3',4',5,7-pentahydroxy-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.049 g/LALOGPS
logP2.41ALOGPS
logP-0.8ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)6.47ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area114.29 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.16 m³·mol⁻¹ChemAxon
Polarizability28.09 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H11O6
IUPAC name2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2H-chromen-2-ylium
InChI IdentifierInChI=1S/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1
InChI KeyVEVZSMAEJFVWIL-UHFFFAOYSA-O
Isomeric SMILESOC1=CC2=[O+]C(=C(O)C=C2C(O)=C1)C1=CC(O)=C(O)C=C1
Average Molecular Weight287.2442
Monoisotopic Molecular Weight287.055563084
Classification
Description belongs to the class of organic compounds known as 7-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-7 position of the flavonoid skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassHydroxyflavonoids
Direct Parent7-hydroxyflavonoids
Alternative Parents
Substituents
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 62.72%; H 3.86%; O 33.42%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, Positivesplash10-0abi-0690000000-173d2265dcd29fa12c94JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ( TMS) - 70eV, Positivesplash10-001i-2062095000-78127582ff2f81e09993JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 20V, positivesplash10-000i-0190000000-5ab24abbf0384667d604JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 20V, positivesplash10-000i-0390000000-cb44415a595e007f6f39JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-0a9fc784dd803d3a889eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-3284da347edb43bf4585JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ti-0970000000-ffb2d72fad14ec3d596aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-b5bd359053422415d91aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-c2b4878a408c4329c697JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-4950000000-95db0e67894990e7b23aJSpectraViewer
ChemSpider ID61546
ChEMBL IDCHEMBL511367
KEGG Compound IDC05905
Pubchem Compound ID68247
Pubchem Substance IDNot Available
ChEBI ID27843
Phenol-Explorer ID19
DrugBank IDNot Available
HMDB IDHMDB02708
CRC / DFC (Dictionary of Food Compounds) IDCMQ73-Z:CMQ73-Z
EAFUS IDNot Available
Dr. Duke IDCYANIDIN
BIGG IDNot Available
KNApSAcK IDC00006614
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCyanidin
Phenol-Explorer Metabolite ID19
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allelochemicDUKE
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
copper chelator38161 A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate.DUKE
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
prooxidantDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— 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.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.