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Showing Compound cyanidin-3,5-diglucoside (FDB030758)

Record Information
Version1.0
Creation date2015-05-07 20:01:24 UTC
Update date2019-11-26 03:21:53 UTC
Primary IDFDB030758
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecyanidin-3,5-diglucoside
DescriptionCyanidin-3,5-diglucoside is a member of the class of compounds known as anthocyanidin-5-o-glycosides. Anthocyanidin-5-o-glycosides are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C5-position. Cyanidin-3,5-diglucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Cyanidin-3,5-diglucoside can be found in a number of food items such as winged bean, evening primrose, durian, and peppermint, which makes cyanidin-3,5-diglucoside a potential biomarker for the consumption of these food products.
CAS Number20905-74-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H31O16
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
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
Isomeric 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
Average Molecular Weight611.5254
Monoisotopic Molecular Weight611.161209944
Classification
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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT 42V, positivesplash10-000b-0040900000-b7c1c9b98b5a9bcf14a1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 42V, positivesplash10-000b-0060900000-04a08790d5db6fe923c3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0030910000-ae40dfcba5a2130d9517Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190700000-bd8e34c577b7cf0fe0d4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0490100000-2f96af11ee69e56346a8Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
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 IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference