Petunidin 3-(6''-acetylglucoside) (CHEM023849)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:19:46 UTC
Update Date2016-11-09 01:17:47 UTC
Accession NumberCHEM023849
Identification
Common NamePetunidin 3-(6''-acetylglucoside)
ClassSmall Molecule
DescriptionPetunidin 3-O-(acetylglucoside) is an anthocyanin, which is a class of polyphenol. Anthocyanins are plant pigments found in many red berries including grape and grape skin. The cell wall of S. cerevisiae is permeable to anthocyanins and as a consequence the anthocyanins can be retained by yeast during wine-making, which can have an influence on wine color. [PMID: 12822951]
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC24H25O13
Average Molecular Mass521.448 g/mol
Monoisotopic Mass521.130 g/mol
CAS Registry Number122731-05-9
IUPAC Name3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium
Traditional Name3-{[(2S,3R,4S,5S,6R)-6-[(acetyloxy)methyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-1lambda4-chromen-1-ylium
SMILESCOC1=C(O)C(O)=CC(=C1)C1=[O+]C2=CC(O)=CC(O)=C2C=C1O[C@@H]1O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O
InChI IdentifierInChI=1S/C24H24O13/c1-9(25)34-8-18-20(30)21(31)22(32)24(37-18)36-17-7-12-13(27)5-11(26)6-15(12)35-23(17)10-3-14(28)19(29)16(4-10)33-2/h3-7,18,20-22,24,30-32H,8H2,1-2H3,(H3-,26,27,28,29)/p+1/t18-,20-,21+,22-,24-/m1/s1
InChI KeyGPUBWXUQPURXOQ-BKSKZGTRSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as anthocyanidin-3-o-glycosides. These are phenolic compounds containing one anthocyanidin moiety which is O-glycosidically linked to a carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin-3-O-glycosides
Alternative Parents
Substituents
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • Anthocyanidin
  • O-glycosyl compound
  • Glycosyl compound
  • Methoxyphenol
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Catechol
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Acetal
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • 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 Solubility0.38 g/LALOGPS
logP1.85ALOGPS
logP0.56ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area208.74 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity131.87 m³·mol⁻¹ChemAxon
Polarizability50.16 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-00di-1000090000-6d5a8dfa1d236f2d308cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1000090000-b66922539ea1b4bb88c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rf-9512000000-e05ac0d7df18beeccd6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-9210070000-1e23f673769a90acb0feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000010000-7452af058240e9896e07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-fe8afb22b3da5e0516baSpectrum
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 IDHMDB0301901
FooDB IDFDB001591
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID30779241
ChEBI IDNot Available
PubChem Compound ID101922116
Kegg Compound IDNot Available
YMDB IDYMDB01771
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available