Cyanidin 3-O-[4-Hydroxycinnamoyl-(->6)-[4-hydroxy-3,5-dimethoxycinnamoyl-(->2)-b-D-glucopyranosyl-(1->2)]-b-D-glucopyranoside] 5-O-(6-O-malonyl-b-D-glucopyranoside) (CHEM027887)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:03:28 UTC
Update Date2016-11-09 01:18:33 UTC
Accession NumberCHEM027887
Identification
Common NameCyanidin 3-O-[4-Hydroxycinnamoyl-(->6)-[4-hydroxy-3,5-dimethoxycinnamoyl-(->2)-b-D-glucopyranosyl-(1->2)]-b-D-glucopyranoside] 5-O-(6-O-malonyl-b-D-glucopyranoside)
ClassSmall Molecule
DescriptionConstituent of Brassica campestris variety chinensis. Cyanidin 3-O-[4-Hydroxycinnamoyl-(->6)-[4-hydroxy-3,5-dimethoxycinnamoyl-(->2)-b-D-glucopyranosyl-(1->2)]-b-D-glucopyranoside] 5-O-(6-O-malonyl-b-D-glucopyranoside) is found in brassicas.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,3',4',5,7-Pentahydroxyflavylium(1+)HMDB
3-O-[4-Hydroxycinnamoyl-(->6)-[4-hydroxy-3,5-dimethoxycinnamoyl-(->2)-b-D-glucopyranosyl-(1->2)]-b-D-glucopyranoside], 5-O-(6-O-malonyl-b-D-glucopyranoside)HMDB
Chemical FormulaC56H59O30
Average Molecular Mass1212.050 g/mol
Monoisotopic Mass1211.309 g/mol
CAS Registry Number200396-70-9
IUPAC Name5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-3-({3-[(4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)oxan-2-yl)oxy]-4,5-dihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-7-hydroxy-1λ⁴-chromen-1-ylium
Traditional Name5-[(6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl)oxy]-3-({3-[(4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)oxan-2-yl)oxy]-4,5-dihydroxy-6-({[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl}oxy)-2-(3,4-dihydroxyphenyl)-7-hydroxy-1λ⁴-chromen-1-ylium
SMILESCOC1=CC(\C=C\C(=O)OC2C(OC3C(OC4=CC5=C(OC6OC(COC(=O)CC(O)=O)C(O)C(O)C6O)C=C(O)C=C5[O+]=C4C4=CC=C(O)C(O)=C4)OC(COC(=O)\C=C\C4=CC=C(O)C=C4)C(O)C3O)OC(CO)C(O)C2O)=CC(OC)=C1O
InChI IdentifierInChI=1S/C56H58O30/c1-75-33-13-24(14-34(76-2)43(33)67)6-12-41(65)85-52-48(72)44(68)36(20-57)82-56(52)86-53-49(73)46(70)38(21-77-40(64)11-5-23-3-8-26(58)9-4-23)84-55(53)81-35-18-28-31(79-51(35)25-7-10-29(60)30(61)15-25)16-27(59)17-32(28)80-54-50(74)47(71)45(69)37(83-54)22-78-42(66)19-39(62)63/h3-18,36-38,44-50,52-57,68-74H,19-22H2,1-2H3,(H5-,58,59,60,61,62,63,64,65,67)/p+1
InChI KeyLWSFQZYPYMWZSK-UHFFFAOYSA-O
Chemical Taxonomy
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 ParentsNot Available
SubstituentsNot Available
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 Solubility0.13 g/LALOGPS
logP2.56ALOGPS
logP2.22ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area466.17 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity292.33 m³·mol⁻¹ChemAxon
Polarizability115.27 ųChemAxon
Number of Rings8ChemAxon
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, Positivesplash10-03e9-1090000000-a2eed66a32a9743cba04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-1090000000-9f9a370f47e7b982846dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l7-9550010021-56e5389223f5fdf97c46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2090000000-1e468575f05b3c9ebf40Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bu0-9360000000-71fffff36cc12fdeb654Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfu-9400000000-e0a5fba0addd10e127b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-1940000003-edb7fdbcc1a6f2132cc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-0540000019-a0b53ff73cd7ad7bfd2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0941010012-2044e42588f22246dffcSpectrum
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 IDHMDB0033725
FooDB IDFDB011848
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 ID131751484
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.