delphinidin 3-O-glucosyl-5-O-caffeoylglucoside (CHEM042199)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:54:24 UTC
Update Date2016-11-09 01:22:37 UTC
Accession NumberCHEM042199
Identification
Common Namedelphinidin 3-O-glucosyl-5-O-caffeoylglucoside
ClassSmall Molecule
DescriptionDelphinidin 3-o-glucosyl-5-o-caffeoylglucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Delphinidin 3-o-glucosyl-5-o-caffeoylglucoside can be found in a number of food items such as pear, apple, banana, and garden tomato, which makes delphinidin 3-o-glucosyl-5-o-caffeoylglucoside a potential biomarker for the consumption of these food products.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC36H36O20
Average Molecular Mass788.664 g/mol
Monoisotopic Mass788.180 g/mol
CAS Registry NumberNot Available
IUPAC Name5-{[6-({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium-7-olate
Traditional Name5-{[6-({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium-7-olate
SMILESOCC1OC(OC2=CC3=C(C=C([O-])C=C3OC3OC(COC(=O)C=CC4=CC(O)=C(O)C=C4)C(O)C(O)C3O)[O+]=C2C2=CC(O)=C(O)C(O)=C2)C(O)C(O)C1O
InChI IdentifierInChI=1S/C36H36O20/c37-11-24-28(45)30(47)32(49)36(55-24)54-23-10-16-21(52-34(23)14-6-19(41)27(44)20(42)7-14)8-15(38)9-22(16)53-35-33(50)31(48)29(46)25(56-35)12-51-26(43)4-2-13-1-3-17(39)18(40)5-13/h1-10,24-25,28-33,35-37,45-50H,11-12H2,(H5-,38,39,40,41,42,43,44)
InChI KeyIKPXCKVGTSPZDV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as anthocyanidin 5-o-6-p-coumaroyl glycosides. These are anthocyanidin 5-O-glycosides where the carbohydrate moiety is esterified at the C6 position with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin 5-O-6-p-coumaroyl glycosides
Alternative Parents
Substituents
  • Anthocyanidin 5-o-6-p-coumaroyl-glycoside
  • Anthocyanidin-3-o-glycoside
  • Anthocyanidin-5-o-glycoside
  • Anthocyanin
  • Flavonoid-3-o-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Benzenetriol
  • Pyrogallol derivative
  • Catechol
  • Styrene
  • Phenoxide
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Oxane
  • Fatty acyl
  • Monosaccharide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Organic zwitterion
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.45 g/LALOGPS
logP2.01ALOGPS
logP0.57ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.61ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area342.18 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity204.46 m³·mol⁻¹ChemAxon
Polarizability74.87 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00y1-0613906600-0d237d277e17528f7cc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0529703100-1f01e967d614bd656d39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-1938300100-b03865b07a44caaa4f8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-0901201400-5208aaa3693842f18a12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0911301100-379fd208f9cdedcc6efeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01tc-2935300000-14bac4d3656ae70d6fc5Spectrum
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 IDNot Available
FooDB IDFDB030809
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available