Record Information
Version1.0
Creation date2010-04-08 22:05:16 UTC
Update date2020-02-24 19:10:26 UTC
Primary IDFDB002177
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Feruloyl-1-sinapoylgentiobiose
Description4,5-Dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. 4,5-Dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 4,5-Dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate is found , on average, in the highest concentration in broccoli. 4,5-Dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate has also been detected, but not quantified in, brassicas. This could make 4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate a potential biomarker for the consumption of these foods.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
4,5-Dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acidGenerator
2-Feruloyl-1-sinapoylgentiobiosedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.37 g/LALOGPS
logP0.88ALOGPS
logP0.28ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)9.19ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area269.82 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity170.82 m³·mol⁻¹ChemAxon
Polarizability72.81 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC33H40O18
IUPAC name4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
InChI IdentifierInChI=1S/C33H40O18/c1-44-18-10-15(4-7-17(18)35)5-8-23(36)50-31-29(42)27(40)22(14-47-32-30(43)28(41)26(39)21(13-34)48-32)49-33(31)51-24(37)9-6-16-11-19(45-2)25(38)20(12-16)46-3/h4-12,21-22,26-35,38-43H,13-14H2,1-3H3/b8-5+,9-6+
InChI KeyQYKVHEQRAXPEEL-XVYDYJIPSA-N
Isomeric SMILESCOC1=CC(\C=C\C(=O)OC2OC(COC3OC(CO)C(O)C(O)C3O)C(O)C(O)C2OC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC(OC)=C1O
Average Molecular Weight724.6599
Monoisotopic Molecular Weight724.221464476
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
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Phenol ether
  • Phenoxy compound
  • Methoxybenzene
  • Styrene
  • Anisole
  • Fatty acid ester
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.70%; H 5.56%; O 39.74%DFC
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 Data330 () (no solvent reported)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3940032300-258f6d833b48ddadcb57JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0491040300-146ab4f3a8a5fd83f528JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0892020000-af7ce0807f84d72071b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-2956010100-bdd1713b2447fea04728JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0490110100-00073d3729fe2dc32660JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05bf-0941010100-af946ddf7b7874120542JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-1920000000-0d221c5a414136a3d50eJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID510
DrugBank IDNot Available
HMDB IDHMDB30334
CRC / DFC (Dictionary of Food Compounds) IDCPD88-P:CGO84-D
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.