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Showing Compound Petunidin 3-(6''-p-coumaroyl-glucoside) (FDB000041)

Record Information
Version1.0
Creation date2010-04-08 22:04:25 UTC
Update date2019-11-26 02:54:30 UTC
Primary IDFDB000041
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePetunidin 3-(6''-p-coumaroyl-glucoside)
DescriptionPetunidin 3-(6''-p-coumaroyl-glucoside) is a member of the class of compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. Anthocyanidin 3-o-6-p-coumaroyl glycosides are anthocyanidin 3-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. Petunidin 3-(6''-p-coumaroyl-glucoside) is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Petunidin 3-(6''-p-coumaroyl-glucoside) can be found in a number of food items such as black elderberry, redcurrant, highbush blueberry, and black chokeberry, which makes petunidin 3-(6''-p-coumaroyl-glucoside) a potential biomarker for the consumption of these food products.
CAS Number147-85-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Petunidin 3-O-(6''-p-coumaroyl-glucoside)db_source
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP2.75ALOGPS
logP3.55ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)6.39ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area228.97 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity164.27 m³·mol⁻¹ChemAxon
Polarizability60.99 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC31H29O14
IUPAC name2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-3-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-1lambda4-chromen-1-ylium
InChI IdentifierInChI=1S/C31H28O14/c1-41-22-9-15(8-20(35)26(22)37)30-23(12-18-19(34)10-17(33)11-21(18)43-30)44-31-29(40)28(39)27(38)24(45-31)13-42-25(36)7-4-14-2-5-16(32)6-3-14/h2-12,24,27-29,31,38-40H,13H2,1H3,(H4-,32,33,34,35,36,37)/p+1/t24-,27-,28+,29-,31?/m1/s1
InChI KeyKTFQEFWNLAUGAX-YQUABMASSA-O
Isomeric SMILES[H][C@]1(COC(=O)\C=C\C2=CC=C(O)C=C2)OC(OC2=C([O+]=C3C=C(O)C=C(O)C3=C2)C2=CC(O)=C(O)C(OC)=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
Average Molecular Weight625.5536
Monoisotopic Molecular Weight625.155730636
Classification
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
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1,3-dicarbonyl compound
  • Oxane
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Primary alcohol
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000009000-5b6f88c91958da869b662016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000009000-ee224dfaeafa513b94d62016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02u0-0904016000-6b43d43fdb794de860422016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000009000-1abb3267bc88054d169b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1000009000-8b5a5e145b97c8102f2e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-8911011000-e3f0e119aa3343eebc282016-08-03View 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 ID58
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDPETUNIDIN-3-(6-P-COUMAROYLGLUCOSIDE)
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— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).