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Record Information
Version1.0
Creation date2010-04-08 22:05:16 UTC
Update date2020-02-24 19:10:26 UTC
Primary IDFDB002179
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Feruloyl-1,2'-disinapoylgentiobiose
Description2-Feruloyl-1,2'-disinapoylgentiobiose belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. 2-Feruloyl-1,2'-disinapoylgentiobiose is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Feruloyl-1,2'-disinapoylgentiobiose is found, on average, in the highest concentration within broccoli. 2-Feruloyl-1,2'-disinapoylgentiobiose has also been detected, but not quantified in, brassicas. This could make 2-feruloyl-1,2'-disinapoylgentiobiose a potential biomarker for the consumption of these foods.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
2-[(3,4-Dihydroxy-6-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxan-2-yl)methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoic acidGenerator
2-Feruloyl-1,2'-disinapoylgentiobiosedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
logP2.79ALOGPS
logP2.7ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)8.93ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area314.58 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity225.3 m³·mol⁻¹ChemAxon
Polarizability93.61 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC44H50O22
IUPAC name6-{[(4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)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-3,5-dimethoxyphenyl)prop-2-enoate
InChI IdentifierInChI=1S/C44H50O22/c1-56-25-14-21(6-10-24(25)46)7-11-32(47)65-42-40(55)38(53)31(63-44(42)66-34(49)13-9-23-17-28(59-4)36(51)29(18-23)60-5)20-61-43-41(39(54)37(52)30(19-45)62-43)64-33(48)12-8-22-15-26(57-2)35(50)27(16-22)58-3/h6-18,30-31,37-46,50-55H,19-20H2,1-5H3/b11-7+,12-8+,13-9+
InChI KeyAZUSMVXIHUPOCX-UQYOVKQCSA-N
Isomeric SMILESCOC1=CC(\C=C\C(=O)OC2OC(COC3OC(CO)C(O)C(O)C3OC(=O)\C=C\C3=CC(OC)=C(O)C(OC)=C3)C(O)C(O)C2OC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=CC(OC)=C1O
Average Molecular Weight930.8546
Monoisotopic Molecular Weight930.279373284
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
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxyphenol
  • Tricarboxylic acid or derivatives
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Monocyclic benzene moiety
  • Fatty acyl
  • Oxane
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Ether
  • Acetal
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.77%; H 5.41%; O 37.81%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 Data355 () (No solvent reported)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0561030906-ff39962e18253dbdf810Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0693050502-628f3e139cee230c3e35Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-1986081702-0728a8d0456220bd83c3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05i3-0592012504-f1224458dc59a7d74c5dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05i3-0982120401-c4f226ad0f4a19ccb729Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i3-0970000000-1396f82f01fcb66feb9fSpectrum
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 ID513
DrugBank IDNot Available
HMDB IDHMDB30336
CRC / DFC (Dictionary of Food Compounds) IDCPD88-P:CGO87-G
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.