cyanidin-3,5-diglucoside (CHEM042173)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:53:25 UTC
Update Date2016-11-09 01:22:37 UTC
Accession NumberCHEM042173
Identification
Common Namecyanidin-3,5-diglucoside
ClassSmall Molecule
DescriptionAn anthocyanin cation that is cyanidin(1+) carrying two beta-D-glucosyl residues at positions 3 and 5.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-3-(beta-D-glucopyranosyloxy)-7-hydroxychromenylium-5-yl beta-D-glucopyranosideChEBI
Cyanidin 3,5-di-O-glucosideChEBI
Cyanidin 3,5-diglucosideChEBI
Cyanidin 3,5-O-diglucosideChEBI
Cyanidin 3,5-di-O-beta-D-glucosideKegg
2-(3,4-Dihydroxyphenyl)-3-(b-D-glucopyranosyloxy)-7-hydroxychromenylium-5-yl b-D-glucopyranosideGenerator
2-(3,4-Dihydroxyphenyl)-3-(β-D-glucopyranosyloxy)-7-hydroxychromenylium-5-yl β-D-glucopyranosideGenerator
Cyanidin 3,5-di-O-b-D-glucosideGenerator
Cyanidin 3,5-di-O-β-D-glucosideGenerator
Chemical FormulaC27H31O16
Average Molecular Mass611.525 g/mol
Monoisotopic Mass611.161 g/mol
CAS Registry NumberNot Available
IUPAC Name2-(3,4-dihydroxyphenyl)-7-hydroxy-3,5-bis({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})-1λ⁴-chromen-1-ylium
Traditional Namecyanin
SMILESOC[C@H]1O[C@@H](OC2=CC(O)=CC3=[O+]C(=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C23)C2=CC(O)=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C27H30O16/c28-7-17-19(33)21(35)23(37)26(42-17)40-15-5-10(30)4-14-11(15)6-16(25(39-14)9-1-2-12(31)13(32)3-9)41-27-24(38)22(36)20(34)18(8-29)43-27/h1-6,17-24,26-29,33-38H,7-8H2,(H2-,30,31,32)/p+1/t17-,18-,19-,20-,21+,22+,23-,24-,26-,27-/m1/s1
InChI KeyRDFLLVCQYHQOBU-ZOTFFYTFSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as anthocyanidin-5-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin-5-O-glycosides
Alternative Parents
Substituents
  • Anthocyanidin-3-o-glycoside
  • Anthocyanidin-5-o-glycoside
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Heteroaromatic compound
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Primary alcohol
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility1.51 g/LALOGPS
logP-0.25ALOGPS
logP-2.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.65ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area272.59 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity148.4 m³·mol⁻¹ChemAxon
Polarizability58.11 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 42V, positivesplash10-000b-0040900000-b7c1c9b98b5a9bcf14a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT 42V, positivesplash10-000b-0060900000-04a08790d5db6fe923c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0030910000-ae40dfcba5a2130d9517Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190700000-bd8e34c577b7cf0fe0d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0490100000-2f96af11ee69e56346a8Spectrum
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 IDHMDB0304306
FooDB IDFDB030758
Phenol Explorer IDNot Available
KNApSAcK IDC00038883
BiGG IDNot Available
BioCyc IDCPD-7138
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID390301
ChEBI ID3978
PubChem Compound IDNot Available
Kegg Compound IDC08639
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20971893
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22334328
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22872589
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23735880