Record Information
Version1.0
Creation date2010-04-08 22:05:16 UTC
Update date2020-02-24 19:10:26 UTC
Primary IDFDB002178
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1,2-Disinapoylgentiobiose
Description1,2-Disinapoylgentiobiose belongs to the class of organic compounds known as hydroxycinnamic acid glycosides. These are glycosylated hydoxycinnamic acids derivatives. 1,2-Disinapoylgentiobiose is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,2-Disinapoylgentiobiose is found, on average, in the highest concentration within broccoli. 1,2-Disinapoylgentiobiose has also been detected, but not quantified in, brassicas. This could make 1,2-disinapoylgentiobiose a potential biomarker for the consumption of these foods.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
4,5-Dihydroxy-3-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)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
1,2-DisinapoylgentiobioseMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP0.89ALOGPS
logP0.13ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.99ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area279.05 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity177.29 m³·mol⁻¹ChemAxon
Polarizability75.62 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC34H42O19
IUPAC name4,5-dihydroxy-3-{[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)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/C34H42O19/c1-45-17-9-15(10-18(46-2)25(17)38)5-7-23(36)52-32-30(43)28(41)22(14-49-33-31(44)29(42)27(40)21(13-35)50-33)51-34(32)53-24(37)8-6-16-11-19(47-3)26(39)20(12-16)48-4/h5-12,21-22,27-35,38-44H,13-14H2,1-4H3/b7-5+,8-6+
InChI KeyMBGNTECDWBKCKH-KQQUZDAGSA-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(OC)=C2)=CC(OC)=C1O
Average Molecular Weight754.6859
Monoisotopic Molecular Weight754.232029162
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
  • Dimethoxybenzene
  • Methoxyphenol
  • M-dimethoxybenzene
  • Phenol ether
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Styrene
  • Fatty acid ester
  • Phenol
  • Alkyl aryl ether
  • 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 54.11%; H 5.61%; O 40.28%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, Positivesplash10-06zi-4960072600-43fb9a06b1e89f9f51d0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a5i-0152090600-7c55ed01bd51d4ef6599JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-0587090400-b6e95bf4c4f9ede0f5bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-3459070100-bac721f38bb46635d108JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zor-1490260500-19ff999d3b1689d3501aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00fr-1592040100-e076c64f4c5a574ce1c7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-1490000000-ac8701a41845ae93205dJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID509
DrugBank IDNot Available
HMDB IDHMDB30335
CRC / DFC (Dictionary of Food Compounds) IDCPD88-P:CGO86-F
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.