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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:37 UTC
Update Date2020-02-26 21:23:50 UTC
HMDB IDHMDB0002114
Secondary Accession Numbers
  • HMDB02114
Metabolite Identification
Common NameBisdemethoxycurcumin
DescriptionBisdemethoxycurcumin is a curcuminoid, a component of tumeric. Tumeric is a spice that comes from the root Curcuma longa, a member of the ginger family, Zingaberaceae. It is bright yellow and has been used as a coloring agent in food in the United States. In India, it has been used for centuries as a spice and a food preservative, and also for its various medicinal properties. In Ayurveda (Indian traditional medicine), tumeric has been used for its medicinal properties for various indications and through different routes of administration. It has been used topically on the skin for wounds, blistering diseases such as pemphigus and herpes zoster, for parasitic skin infections, and for acne. It has been used via oral administration for the common cold, liver diseases, urinary tract diseases, and as a blood purifier. For chronic rhinitis and coryza, it has been used via inhalation. The average intake of tumeric in the diet in India is approximately 2 to 2.5 g in a 60 kg individual. This corresponds to an intake of approximately 60 to 100 mg of curcumin daily. The Food and Drug Administration has classified tumeric among substances Generally Recognized as Safe (GRAS). A large number of in vitro and animal studies have been conducted to evaluate the effect of curcumin on inflammation. It has been found to act at various different levels of the arachadonic acid inflammatory cascade and through effects on various enzymes and cytokines. (PMID: 12676044 ).
Structure
Data?1582752230
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
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Bisdemethoxycurcumin,1TMS,#13185.8784https://arxiv.org/abs/1905.12712
Bisdemethoxycurcumin,1TMS,#23402.143https://arxiv.org/abs/1905.12712
Bisdemethoxycurcumin,2TMS,#13212.1462https://arxiv.org/abs/1905.12712
Bisdemethoxycurcumin,2TMS,#23497.3137https://arxiv.org/abs/1905.12712
Bisdemethoxycurcumin,2TMS,#33498.7026https://arxiv.org/abs/1905.12712
Bisdemethoxycurcumin,1TBDMS,#13451.838https://arxiv.org/abs/1905.12712
Bisdemethoxycurcumin,1TBDMS,#23698.4917https://arxiv.org/abs/1905.12712
Bisdemethoxycurcumin,2TBDMS,#13807.1238https://arxiv.org/abs/1905.12712
Bisdemethoxycurcumin,2TBDMS,#24016.631https://arxiv.org/abs/1905.12712
Bisdemethoxycurcumin,2TBDMS,#34018.604https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-0900000000-80dee0b7da47096385f32017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01b9-4693400000-4dfcfa07fb4fcf08d15a2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , negativesplash10-000f-0900000000-b6262ce6a5bc848338cc2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0319000000-51bdfbd78f352db8c2332017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0911000000-feb1ff110feb9ee4d6442017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0690-3900000000-80607bb0dba3055c2ec42017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0109000000-d6136d3ecd9a3055073b2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0918000000-8da010127482f9dbe8372017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07vl-1910000000-7b9ad6f38949b0ffed212017-09-01View Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
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 References
  1. 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. [PubMed:12676044 ]