Showing metabocard for Bisdemethoxycurcumin (BMDB0002114)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:51:22 UTC
Update Date2020-04-22 15:09:47 UTC
BMDB IDBMDB0002114
Secondary Accession Numbers
  • BMDB02114
Metabolite Identification
Common NameBisdemethoxycurcumin
DescriptionBisdemethoxycurcumin, also known as curcumin III, 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. Based on a literature review a significant number of articles have been published on Bisdemethoxycurcumin.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dioneChEBI
Bis(4-hydroxycinnamoyl)methaneChEBI
Bis(p-hydroxycinnamoyl)methaneChEBI
Curcumin IIIChEBI
DidemethoxycurcuminChEBI
1,7-Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione(e,e)HMDB
Bis-demethoxycurcuminHMDB
Chemical FormulaC19H16O4
Average Molecular Weight308.3279
Monoisotopic Molecular Weight308.104859
IUPAC Name(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
Traditional Namebisdemethoxycurcumin
CAS Registry Number24939-16-0
SMILES
OC1=CC=C(\C=C\C(=O)CC(=O)\C=C\C2=CC=C(O)C=C2)C=C1
InChI Identifier
InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
InChI KeyPREBVFJICNPEKM-YDWXAUTNSA-N
Chemical Taxonomy
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
  • Bis-desmethoxycurcumin
  • Hydroxycinnamic acid or derivatives
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1,3-diketone
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Monocyclic benzene moiety
  • Enone
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.46ALOGPS
logP4.44ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity90.88 m³·mol⁻¹ChemAxon
Polarizability32.58 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-0900000000-80dee0b7da47096385f3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-4693400000-4dfcfa07fb4fcf08d15aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , negativesplash10-000f-0900000000-b6262ce6a5bc848338ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0319000000-51bdfbd78f352db8c233View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0911000000-feb1ff110feb9ee4d644View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0690-3900000000-80607bb0dba3055c2ec4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0109000000-d6136d3ecd9a3055073bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0918000000-8da010127482f9dbe837View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07vl-1910000000-7b9ad6f38949b0ffed21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ap0-0907000000-a0e824005455e435a22bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0924000000-b8be7e1dc7f7aebc8446View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0920000000-3f12cad48a69d6a54824View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0309000000-59ab1e9ec81516f1adcbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-b4cdb8c134bf3a01b5ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0910000000-297489cfaed0405d2f7aView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002114
DrugBank IDNot Available
Phenol Explorer Compound ID715
FooDB IDFDB011961
KNApSAcK IDC00032769
Chemspider ID4474770
KEGG Compound IDNot Available
BioCyc IDCPD-12188
BiGG IDNot Available
Wikipedia LinkBisdemethoxycurcumin
METLIN IDNot Available
PubChem Compound5315472
PDB IDNot Available
ChEBI ID71045
References
Synthesis ReferencePark So-Young; Kim Darrick S H L Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimer's disease. Journal of natural products (2002), 65(9), 1227-31.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available