Record Information
Version1.0
Creation date2010-04-08 22:09:55 UTC
Update date2018-05-28 23:32:51 UTC
Primary IDFDB011964
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDemethoxycurcumin
DescriptionIsolated from Curcuma zedoaria (zedoary), Curcuma longa (turmeric), Curcuma xanthorrhiza (Java turmeric). Demethoxycurcumin is found in many foods, some of which are beverages, herbs and spices, turmeric, and root vegetables.
CAS Number22608-11-3
Structure
Thumb
Synonyms
SynonymSource
(1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dioneChEBI
(1E,6E)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dioneChEBI
4-Hydroxycinnamoyl(feroyl)methaneChEBI
4-Hydroxycinnamoyl(feruloyl)methaneChEBI
BHCFMChEBI
CurcuminIIChEBI
Feruloyl-p-hydroxycinnnamoylmethaneChEBI
1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9ciHMDB
Demethoxy-curcuminHMDB
MonodemethoxycurcuminHMDB
p-HydroxycinnamoylferuloylmethaneHMDB
Curcumin IIMeSH
(1e,6e)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dioneChEBI
(1e,6e)-1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-hepta-1,6-diene-3,5-dioneChEBI
1-(4-Hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione, 9CIdb_source
4-hydroxycinnamoyl(feroyl)methanebiospider
Bhcfmbiospider
Demethoxycurcumindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.0067 g/LALOGPS
logP3.54ALOGPS
logP4.28ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)8.84ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.35 m³·mol⁻¹ChemAxon
Polarizability35.35 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H18O5
IUPAC name(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
InChI IdentifierInChI=1S/C20H18O5/c1-25-20-12-15(6-11-19(20)24)5-10-18(23)13-17(22)9-4-14-2-7-16(21)8-3-14/h2-12,21,24H,13H2,1H3/b9-4+,10-5+
InChI KeyHJTVQHVGMGKONQ-LUZURFALSA-N
Isomeric SMILESCOC1=CC(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)=CC=C1O
Average Molecular Weight338.3539
Monoisotopic Molecular Weight338.115423686
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
  • Desmethoxycurcumin
  • Hydroxycinnamic acid or derivatives
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Phenol
  • 1,3-diketone
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Monocyclic benzene moiety
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Enone
  • Ketone
  • Ether
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.00%; H 5.36%; O 23.64%DFC
Melting PointMp 168°DFC
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r2-0901000000-654fca3f02d69e7560dbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-014i-3071900000-50aab8ffd9b366fd14d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0419000000-127d78c62fb7431896b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0901000000-c40b24a8778d2fa9787dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002b-1900000000-82aa8b73d450c54c4c30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0309000000-1e9e9a7c9cdc0d078ad5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000j-0914000000-656374264de68ab93dd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07xs-1911000000-d77a4b8103374473002fView in MoNA
ChemSpider ID4579941
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5469424
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID714
DrugBank IDNot Available
HMDB IDHMDB33801
CRC / DFC (Dictionary of Food Compounds) IDHFR53-E:HCC54-N
EAFUS IDNot Available
Dr. Duke IDMONODEMETHOXYCURCUMIN|MONODESMETHOXYCURCUMIN|DEMETHOXYCURCUMIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET 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
anti aflatoxin35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti amyloid-betaDUKE
anti angiogenic48422 An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leishmanic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti lipoperoxidantDUKE
anti mutagenicDUKE
anti nitrosatingDUKE
anti papillomic22587 A substance that destroys or inhibits replication of viruses.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
DNA-protectiveDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
nitric-oxide scavengerDUKE
plasmodicideDUKE
quinone-reductase inducerDUKE
sortase-A inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
topoisomerase-II inhibitor50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
topoisomerase-I inhibitor50276 A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.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— 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.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).