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Delphinidin 3-[6''-(4'''-p-coumaroylrhamnosyl)glucoside] 5-glucoside (FDB000680)

Record Information
Version1.0
Creation date2010-04-08 22:04:40 UTC
Update date2019-11-26 02:55:12 UTC
Primary IDFDB000680
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDelphinidin 3-[6''-(4'''-p-coumaroylrhamnosyl)glucoside] 5-glucoside
DescriptionDelphinidin 3-[6''-(4'''-p-coumaroylrhamnosyl)glucoside] 5-glucoside 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. Delphinidin 3-[6''-(4'''-p-coumaroylrhamnosyl)glucoside] 5-glucoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Delphinidin 3-[6''-(4'''-p-coumaroylrhamnosyl)glucoside] 5-glucoside can be found in eggplant and potato, which makes delphinidin 3-[6''-(4'''-p-coumaroylrhamnosyl)glucoside] 5-glucoside a potential biomarker for the consumption of these food products.
CAS Number28463-30-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP1.68ALOGPS
logP-0.18ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.61ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area378.04 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity222.8 m³·mol⁻¹ChemAxon
Polarizability89.63 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC42H47O23
IUPAC name3-[(6-{[(3,5-dihydroxy-4-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-6-methyloxan-2-yl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-7-hydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C42H46O23/c1-15-29(49)39(65-28(48)7-4-16-2-5-18(44)6-3-16)37(57)40(59-15)58-14-27-32(52)34(54)36(56)42(64-27)62-25-12-20-23(60-38(25)17-8-21(46)30(50)22(47)9-17)10-19(45)11-24(20)61-41-35(55)33(53)31(51)26(13-43)63-41/h2-12,15,26-27,29,31-37,39-43,49,51-57H,13-14H2,1H3,(H4-,44,45,46,47,48,50)/p+1
InChI KeyHYLOPHQDODSUIK-UHFFFAOYSA-O
Isomeric SMILESCC1OC(OCC2OC(OC3=CC4=C(OC5OC(CO)C(O)C(O)C5O)C=C(O)C=C4[O+]=C3C3=CC(O)=C(O)C(O)=C3)C(O)C(O)C2O)C(O)C(OC(=O)\C=C\C2=CC=C(O)C=C2)C1O
Average Molecular Weight919.8088
Monoisotopic Molecular Weight919.25081281
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-5-o-glycoside
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Coumaric acid ester
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Hydroxycinnamic acid or derivatives
  • O-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Benzenetriol
  • Pyrogallol derivative
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty acyl
  • Oxane
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.84%; H 5.15%; O 40.01%DFC
Melting PointMp 194-196 dec. (chloride)DFC
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
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0100000009-8d51cb06abcb0b9707d42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0200000009-67ebafa30a566367aeb12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-6900000202-586d8287d5720a9ef2992016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1200000009-221d9824acfa54cf08fc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00or-4500000009-08fafd204c875fe61df12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-9100000000-dc962fe73a0c34a242d62016-08-03View Spectrum
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) IDOJK56-Z:BFM84-B
EAFUS IDNot Available
Dr. Duke IDNASUNIN
BIGG IDNot Available
KNApSAcK IDC00006893
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 IDSCMR96-N:BFM84-B
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.