Record Information
Version1.0
Creation date2015-05-07 20:00:30 UTC
Update date2019-11-26 03:21:53 UTC
Primary IDFDB030751
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namecurcumin 4'-O-β-D-gentiobioside
DescriptionCurcumin 4'-o-β-d-gentiobioside is a member of the class of compounds known as curcuminoids. Curcuminoids are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. Curcumin 4'-o-β-d-gentiobioside is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Curcumin 4'-o-β-d-gentiobioside can be found in a number of food items such as brassicas, narrowleaf cattail, fireweed, and soursop, which makes curcumin 4'-o-β-d-gentiobioside a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP0.49ALOGPS
logP-0.28ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.87ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area254.52 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity170.68 m³·mol⁻¹ChemAxon
Polarizability70.95 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC33H40O16
IUPAC name5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(3-methoxy-4-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}phenyl)hepta-1,4,6-trien-3-one
InChI IdentifierInChI=1S/C33H40O16/c1-44-22-11-16(5-9-20(22)37)3-7-18(35)13-19(36)8-4-17-6-10-21(23(12-17)45-2)47-33-31(43)29(41)27(39)25(49-33)15-46-32-30(42)28(40)26(38)24(14-34)48-32/h3-13,24-35,37-43H,14-15H2,1-2H3
InChI KeyIHJHVEOMJHXPKL-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(C=CC(O)=CC(=O)C=CC2=CC(OC)=C(OC3OC(COC4OC(CO)C(O)C(O)C4O)C(O)C(O)C3O)C=C2)=CC=C1O
Average Molecular Weight692.667
Monoisotopic Molecular Weight692.231635208
Classification
Description Belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentCurcuminoids
Alternative Parents
Substituents
  • Curcumin
  • Phenolic glycoside
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Acetal
  • Oxacycle
  • Enol
  • Ether
  • Organoheterocyclic compound
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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, Positivesplash10-00or-0619027000-1a99c47603faec28bf5bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00or-0906010000-f23bdc9f32dfe620e5f6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00n0-0913000000-5bc6109c2332da76e81fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00mo-1926037000-811596ab3ef94001f698Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01di-2709013000-16e46fcb670c647f5cb7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1219000000-ac703c42d8d353856fe6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01u0-0606095000-401813c8b9234d461f34Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-029j-0519054000-82e86ce122cf41918d82Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-2916021000-d2b957b6ff6f29f3f5d1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014m-0839588000-be17dcef2234615d1aa1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0759-4805493000-ba6839ef4a1aab4db46cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-4409002000-23875b5c9a75b9f6b8e6Spectrum
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 IDNot Available
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