Bisdemethoxycurcumin (CHEM027947)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:06:35 UTC
Update Date2016-11-09 01:18:34 UTC
Accession NumberCHEM027947
Identification
Common NameBisdemethoxycurcumin
ClassSmall Molecule
DescriptionA beta-diketone that is methane in which two of the hydrogens are substituted by 4-hydroxycinnamoyl groups.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass308.328 g/mol
Monoisotopic Mass308.105 g/mol
CAS Registry Number33171-05-0
IUPAC Name(1E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
Traditional Namebisdemethoxycurcumin
SMILESO\C(\C=C\C1=CC=C(O)C=C1)=C/C(=O)/C=C/C1=CC=C(O)C=C1
InChI IdentifierInChI=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/h1-13,20-22H/b11-5+,12-6+,18-13-
InChI KeyYXAKCQIIROBKOP-HSSGTREWSA-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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-0900000000-80dee0b7da47096385f3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-4693400000-4dfcfa07fb4fcf08d15aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , negativesplash10-000f-0900000000-b6262ce6a5bc848338ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0319000000-51bdfbd78f352db8c233Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0911000000-feb1ff110feb9ee4d644Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0690-3900000000-80607bb0dba3055c2ec4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0109000000-d6136d3ecd9a3055073bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0918000000-8da010127482f9dbe837Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07vl-1910000000-7b9ad6f38949b0ffed21Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ap0-0907000000-a0e824005455e435a22bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0924000000-b8be7e1dc7f7aebc8446Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0920000000-3f12cad48a69d6a54824Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0309000000-59ab1e9ec81516f1adcbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-b4cdb8c134bf3a01b5ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0910000000-297489cfaed0405d2f7aSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002114
FooDB IDFDB011961
Phenol Explorer ID715
KNApSAcK IDC00032769
BiGG IDNot Available
BioCyc IDCPD-12188
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBisdemethoxycurcumin
Chemspider ID4474770
ChEBI ID71045
PubChem Compound ID5315472
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20953820
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21041675
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21136025
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21484077
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21640982
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21856253
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21933103
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21941764
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21968952
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22029407
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22145830
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22156608
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22207005
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22237476
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22434443
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22457548
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22531131
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22566109
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22725836
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=22753036
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=22768090
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=22849866
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=22928089
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=22980852
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=23079892
26. Park 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.
27. Chainani-Wu N: Safety and anti-inflammatory activity of curcumin: a component of tumeric (Curcuma longa). J Altern Complement Med. 2003 Feb;9(1):161-8.