Record Information
Version1.0
Creation date2010-04-08 22:04:30 UTC
Update date2019-11-26 02:54:37 UTC
Primary IDFDB000270
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,2,2'-Triferuloylgentiobiose
Description1,2,2'-triferuloylgentiobiose is a member of the class of compounds known as hydroxycinnamic acid glycosides. Hydroxycinnamic acid glycosides are glycosylated hydoxycinnamic acids derivatives. 1,2,2'-triferuloylgentiobiose is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 1,2,2'-triferuloylgentiobiose can be found in broccoli, which makes 1,2,2'-triferuloylgentiobiose a potential biomarker for the consumption of this food product.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP2.76ALOGPS
logP3.01ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area296.12 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity212.37 m³·mol⁻¹ChemAxon
Polarizability85.68 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC42H46O20
IUPAC name(2S,3R,4S,5S,6R)-6-({[(2R,3R,4S,5S,6R)-4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
InChI IdentifierInChI=1S/C42H46O20/c1-54-27-16-21(4-10-24(27)44)7-13-32(47)60-39-37(52)35(50)30(19-43)58-41(39)57-20-31-36(51)38(53)40(61-33(48)14-8-22-5-11-25(45)28(17-22)55-2)42(59-31)62-34(49)15-9-23-6-12-26(46)29(18-23)56-3/h4-18,30-31,35-46,50-53H,19-20H2,1-3H3/b13-7+,14-8+,15-9+/t30-,31-,35-,36-,37+,38+,39-,40-,41-,42+/m1/s1
InChI KeyKHUQBGCNTVZZRF-BQCRRWLHSA-N
Isomeric SMILESCOC1=CC(\C=C\C(=O)O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3OC(=O)\C=C\C3=CC=C(O)C(OC)=C3)[C@@H](O)[C@H](O)[C@H]2OC(=O)\C=C\C2=CC=C(O)C(OC)=C2)=CC=C1O
Average Molecular Weight870.8026
Monoisotopic Molecular Weight870.258243912
Classification
Description Belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acid glycosides
Alternative Parents
Substituents
  • Hydroxycinnamic acid glycoside
  • O-cinnamoyl glycoside
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Methoxyphenol
  • Tricarboxylic acid or derivatives
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Fatty acyl
  • Monocyclic benzene moiety
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Ether
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
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, Positivesplash10-0fba-0601129160-32b42942e707f645d8efSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0904054120-9149cd2ad38558a6f35eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fbj-0805159220-4be4fa7c23978133fc5dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00mo-0822129040-fe556f4eac24cd53a3b7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0912313110-d0b9f822fb221636da36Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-de2e2fbe0eb4601458b0Spectrum
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 ID515
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
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
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.