Petunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside (CHEM023968)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:24:01 UTC
Update Date2016-11-09 01:17:48 UTC
Accession NumberCHEM023968
Identification
Common NamePetunidin 3-O-[6-O-(4-O-(E)-caffeoyl-O-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-O-beta-glucopyranoside
ClassSmall Molecule
DescriptionPetunidin 3-o-[6-o-(4-o-(e)-caffeoyl-o-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-o-beta-glucopyranoside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Petunidin 3-o-[6-o-(4-o-(e)-caffeoyl-o-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-o-beta-glucopyranoside can be found in potato, which makes petunidin 3-o-[6-o-(4-o-(e)-caffeoyl-o-alpha-rhamnopyranosyl)-beta-glucopyranoside]-5-o-beta-glucopyranoside a potential biomarker for the consumption of this food product.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Petunidin 3-O-[6-O-(4-O-(e)-caffeoyl-O-a-rhamnopyranosyl)-b-glucopyranoside]-5-O-b-glucopyranosideGenerator
Petunidin 3-O-[6-O-(4-O-(e)-caffeoyl-O-α-rhamnopyranosyl)-β-glucopyranoside]-5-O-β-glucopyranosideGenerator
Chemical FormulaC43H49O24
Average Molecular Mass949.835 g/mol
Monoisotopic Mass949.261 g/mol
CAS Registry Number232617-23-1
IUPAC Name2-(3,4-dihydroxy-5-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-6-({[(2R,3R,4S,5R,6R)-5-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-6-methyloxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
Traditional Name2-(3,4-dihydroxy-5-methoxyphenyl)-3-{[(2S,3R,4S,5S,6R)-6-({[(2R,3R,4S,5R,6R)-5-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-6-methyloxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium
SMILESCOC1=C(O)C(O)=CC(=C1)C1=[O+]C2=CC(O)=CC(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2C=C1O[C@@H]1O[C@H](CO[C@@H]2O[C@H](C)[C@H](OC(=O)\C=C\C3=CC(O)=C(O)C=C3)[C@@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C43H48O24/c1-15-39(67-29(49)6-4-16-3-5-20(46)21(47)7-16)35(55)38(58)41(61-15)60-14-28-32(52)34(54)37(57)43(66-28)64-26-12-19-23(62-40(26)17-8-22(48)30(50)25(9-17)59-2)10-18(45)11-24(19)63-42-36(56)33(53)31(51)27(13-44)65-42/h3-12,15,27-28,31-39,41-44,51-58H,13-14H2,1-2H3,(H4-,45,46,47,48,49,50)/p+1/t15-,27-,28-,31-,32-,33+,34+,35+,36-,37-,38-,39+,41-,42-,43-/m1/s1
InChI KeyJUOSIPJKJLUJCA-RPFRYSCCSA-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-5-o-glycoside
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Hydroxycinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid or derivatives
  • Cinnamic acid ester
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Methoxyphenol
  • 1-benzopyran
  • Benzopyran
  • Anisole
  • Methoxybenzene
  • Phenoxy compound
  • Phenol ether
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Alkyl aryl ether
  • Oxane
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Polyol
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.46 g/LALOGPS
logP1.7ALOGPS
logP-0.43ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.66ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area387.27 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity229.26 m³·mol⁻¹ChemAxon
Polarizability92.02 ųChemAxon
Number of Rings7ChemAxon
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, Positivesplash10-0udi-0100000009-93411e2dbed9b75fef58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0200000009-2abde7a255a26bbba0fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-5900000104-fcc1664b01e818a58e0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1100000009-710fd1f3caeba02492e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-4500000009-eba783b1eadbd674ddb1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9100100000-50957837b54a6c4616beSpectrum
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 IDFDB001733
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