Record Information
Version1.0
Creation date2010-04-08 22:09:27 UTC
Update date2019-11-26 03:04:32 UTC
Primary IDFDB011081
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCyclocurcumin
DescriptionCyclocurcumin belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. Cyclocurcumin is an extremely weak basic (essentially neutral) compound (based on its pKa). Cyclocurcumin is found, on average, in the highest concentration within turmerics. Cyclocurcumin has also been detected, but not quantified in, herbs and spices. This could make cyclocurcumin a potential biomarker for the consumption of these foods.
CAS Number153127-42-5
Structure
Thumb
Synonyms
SynonymSource
Predicted Properties
PropertyValueSource
Water Solubility0.0073 g/LALOGPS
logP3.11ALOGPS
logP3.24ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.38ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity102.88 m³·mol⁻¹ChemAxon
Polarizability39.02 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H20O6
IUPAC name2-(4-hydroxy-3-methoxyphenyl)-6-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-3,4-dihydro-2H-pyran-4-one
InChI IdentifierInChI=1S/C21H20O6/c1-25-20-9-13(4-7-17(20)23)3-6-16-11-15(22)12-19(27-16)14-5-8-18(24)21(10-14)26-2/h3-11,19,23-24H,12H2,1-2H3/b6-3+
InChI KeyIZLBLUIBVMGMIY-ZZXKWVIFSA-N
Isomeric SMILESCOC1=C(O)C=CC(\C=C\C2=CC(=O)CC(O2)C2=CC(OC)=C(O)C=C2)=C1
Average Molecular Weight368.3799
Monoisotopic Molecular Weight368.125988372
Classification
Description belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentLinear diarylheptanoids
Alternative Parents
Substituents
  • Linear 1,7-diphenylheptane skeleton
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Dihydropyranone
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous ester
  • Ketone
  • Cyclic ketone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 68.47%; H 5.47%; O 26.06%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 Data373 (log e 4.89) (EtOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-0936000000-53b2c461273bb4297b47JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000e-4080900000-149096315ab859a3a05bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0219000000-9e4385afadfbf025a3aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbi-0859000000-8176270cfef6038b6accJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uds-1922000000-3059bd7587308a28ca1aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0109000000-3a265f3d8dcd0b6eac79JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0129000000-0bbd2fdfc37d33f65e71JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fmi-0914000000-4f7363a212d972caa5e7JSpectraViewer
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 IDHMDB33086
CRC / DFC (Dictionary of Food Compounds) IDFYO63-Z:FYO63-Z
EAFUS IDNot Available
Dr. Duke IDCYCLOCURCUMIN
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 / Bioactivities
DescriptorIDDefinitionReference
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).