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Showing Compound Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxycinnamoyl-(->6)]-b-D-glucopyranoside](E-) 5-O-(6-O-malonyl-b-D-glucopyranoside) (FDB014136)

Record Information
Version1.0
Creation date2010-04-08 22:11:06 UTC
Update date2019-11-26 03:09:34 UTC
Primary IDFDB014136
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxycinnamoyl-(->6)]-b-D-glucopyranoside](E-) 5-O-(6-O-malonyl-b-D-glucopyranoside)
DescriptionPelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxycinnamoyl-(->6)]-b-D-glucopyranoside](E-) 5-O-(6-O-malonyl-b-D-glucopyranoside) belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These 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. Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxycinnamoyl-(->6)]-b-D-glucopyranoside](E-) 5-O-(6-O-malonyl-b-D-glucopyranoside) has been detected, but not quantified in, brassicas. This could make pelargonidin 3-O-[b-D-glucopyranosyl-(1->2)-[4-hydroxycinnamoyl-(->6)]-b-D-glucopyranoside](e-) 5-O-(6-O-malonyl-b-D-glucopyranoside) a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Pelargonidin 3-O-[b-D-Glucopyranosyl-(1->2)-[4-hydroxycinnamoyl-(->6)]-b-D-glucopyranoside](E-) 5-O-(6-O-malonyl-b-D-glucopyranoside).
CAS Number218963-76-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP1.18ALOGPS
logP-0.41ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area401.18 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity235.88 m³·mol⁻¹ChemAxon
Polarizability94.69 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC45H49O25
IUPAC name5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-3-{[4,5-dihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-7-hydroxy-2-(4-hydroxyphenyl)-1λ⁴-chromen-1-ylium
InChI IdentifierInChI=1S/C45H48O25/c46-15-27-33(54)36(57)40(61)44(67-27)70-42-38(59)35(56)29(16-62-31(52)10-3-18-1-6-20(47)7-2-18)69-45(42)66-26-13-23-24(64-41(26)19-4-8-21(48)9-5-19)11-22(49)12-25(23)65-43-39(60)37(58)34(55)28(68-43)17-63-32(53)14-30(50)51/h1-13,27-29,33-40,42-46,54-61H,14-17H2,(H3-,47,48,49,50,51,52)/p+1
InChI KeyMEMCAMOQDXSLTL-UHFFFAOYSA-O
Isomeric SMILESOCC1OC(OC2C(O)C(O)C(COC(=O)\C=C\C3=CC=C(O)C=C3)OC2OC2=CC3=C(OC4OC(COC(=O)CC(O)=O)C(O)C(O)C4O)C=C(O)C=C3[O+]=C2C2=CC=C(O)C=C2)C(O)C(O)C1O
Average Molecular Weight989.8556
Monoisotopic Molecular Weight989.256292118
Classification
Description Belongs to the class of organic compounds known as anthocyanidin 3-o-6-p-coumaroyl glycosides. These 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentAnthocyanidin 3-O-6-p-coumaroyl glycosides
Alternative Parents
Substituents
  • Anthocyanidin 3-o-6-p-coumaroyl-glycoside
  • Anthocyanin
  • Anthocyanidin-5-o-glycoside
  • Anthocyanidin-3-o-glycoside
  • Flavonoid-3-o-glycoside
  • 4'-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Anthocyanidin
  • Phenolic glycoside
  • Coumaric acid ester
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Tricarboxylic acid or derivatives
  • Styrene
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • 1,3-dicarbonyl compound
  • Oxane
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Enoate ester
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Polyol
  • Organoheterocyclic compound
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6x-9401000008-a4b0a270fdcbd464e6db2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-9500000008-18e3493f53c65bc7f69e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ikd-9711000010-598d65df35bd73c01bd72016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-4500000009-84c3943518f7fb4be7de2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06vi-5900000002-47edd8a20b1b65ff643f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lxx-9800000000-9b9c9243745439f9029a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-009b-0810050396-4b10b3e3b993718ae4272021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02bf-0920121553-1bc3fd37708f099a77192021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ke-2900000442-bcd4abc9b9165f8e66ca2021-09-23View 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 IDHMDB35452
CRC / DFC (Dictionary of Food Compounds) IDHGV59-L:JOD59-Z
EAFUS IDNot Available
Dr. Duke IDNot Available
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
Processing...
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