2-O-(4-Hydroxycinnamoyl)-1-O-galloyl-beta-D-glucopyranoside (CHEM032525)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 03:27:27 UTC
Update Date2016-11-09 01:20:44 UTC
Accession NumberCHEM032525
Identification
Common Name2-O-(4-Hydroxycinnamoyl)-1-O-galloyl-beta-D-glucopyranoside
ClassSmall Molecule
Description2-O-(4-Hydroxycinnamoyl)-1-O-galloyl-beta-D-glucopyranoside is found in green vegetables. 2-O-(4-Hydroxycinnamoyl)-1-O-galloyl-beta-D-glucopyranoside is isolated from Rheum species.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-O-(4-Hydroxycinnamoyl)-1-O-galloyl-b-D-glucopyranosideGenerator
2-O-(4-Hydroxycinnamoyl)-1-O-galloyl-β-D-glucopyranosideGenerator
4,5-Dihydroxy-6-(hydroxymethyl)-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-2-yl 3,4,5-trihydroxybenzoic acidGenerator
Chemical FormulaC22H22O12
Average Molecular Mass478.403 g/mol
Monoisotopic Mass478.111 g/mol
CAS Registry Number94356-18-0
IUPAC Name4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-2-yl 3,4,5-trihydroxybenzoate
Traditional Name4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-2-yl 3,4,5-trihydroxybenzoate
SMILESOCC1OC(OC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC(=O)\C=C/C2=CC=C(O)C=C2)C(O)C1O
InChI IdentifierInChI=1S/C22H22O12/c23-9-15-18(29)19(30)20(33-16(27)6-3-10-1-4-12(24)5-2-10)22(32-15)34-21(31)11-7-13(25)17(28)14(26)8-11/h1-8,15,18-20,22-26,28-30H,9H2/b6-3-
InChI KeySWCFDHFIUQJCLJ-UTCJRWHESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassNot Available
Direct ParentTannins
Alternative Parents
Substituents
  • Tannin
  • Galloyl ester
  • Tetracarboxylic acid or derivatives
  • Gallic acid or derivatives
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Benzenetriol
  • Benzoic acid or derivatives
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monosaccharide
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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 Solubility0.89 g/LALOGPS
logP1.21ALOGPS
logP1.38ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)8.06ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity113.24 m³·mol⁻¹ChemAxon
Polarizability46.13 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-5912300000-19e9250e9ca1859ef46eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00kb-2921003000-f7a852f9a753903fb220Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_22) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_16) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_4_17) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_14) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("2-O-(4-Hydroxycinnamoyl)-1-O-galloyl-beta-D-glucopyranoside,3TMS,#12" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fmi-0902100000-26ac27b668295a1bc769Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0901000000-1242612221b97abc8d57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-0900000000-8ab446e2b76912791a5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0i29-0902200000-5df274c5a79875b52513Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0901000000-a62bb79ac0c645a5a601Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xs-1900000000-819ac5f5fcde4e7f7806Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0717900000-e4719b58219ff89757ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1941100000-c093f038d3c3a370fed5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-2901100000-d8886e522efd569c7710Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0493100000-0a21be4eefefddf742bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uds-2900000000-2bb88fca02f23bbc6105Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdi-3900100000-107dbc2d268fb223883fSpectrum
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 IDHMDB0039190
FooDB IDFDB018718
Phenol Explorer IDNot Available
KNApSAcK IDC00055240
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131752570
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.