Record Information
Version1.0
Creation date2010-04-08 22:14:37 UTC
Update date2018-05-29 01:43:30 UTC
Primary IDFDB019830
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCalebin A
DescriptionConstituent of the rhizomes of Cucuma longa (turmeric). Calebin A is found in turmeric and herbs and spices.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
Calebin-aChEMBL, HMDB
4''-(3'''-methoxy-4'''-hydroxyphenyl)-2''-oxo-3''-enebutanyl 3-(3'-methoxy-4'-hydroxyphenyl)propenoateHMDB
(3E)-4-(4-Hydroxy-3-methoxyphenyl)-2-oxobut-3-en-1-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acidGenerator
4''-(3'''-methoxy-4'''-hydroxyphenyl)-2''-oxo-3''-enebutyl 3-(3'-methoxy-4'-hydroxyphenyl)propenoatemanual
Predicted Properties
PropertyValueSource
Water Solubility0.0078 g/LALOGPS
logP3.54ALOGPS
logP3.76ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.35ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity104.77 m³·mol⁻¹ChemAxon
Polarizability39.91 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H20O7
IUPAC name(3E)-4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-en-1-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
InChI IdentifierInChI=1S/C21H20O7/c1-26-19-11-14(4-8-17(19)23)3-7-16(22)13-28-21(25)10-6-15-5-9-18(24)20(12-15)27-2/h3-12,23-24H,13H2,1-2H3/b7-3+,10-6+
InChI KeyUYEWRTKHKAVRDI-ASVGJQBISA-N
Isomeric SMILESCOC1=C(O)C=CC(\C=C\C(=O)COC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=C1
Average Molecular Weight384.3793
Monoisotopic Molecular Weight384.120902994
Classification
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Styrene
  • Methoxybenzene
  • Phenol
  • Alpha-acyloxy ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Alpha,beta-unsaturated ketone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Acryloyl-group
  • Enone
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 65.62%; H 5.24%; O 29.14%DFC
Melting PointMp 138-139°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data339 (log e 3.73) (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0900000000-2ad529702fd246d70512View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2180290000-22a6d9ea77f0e5ac9e3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0719000000-07ead4a60a17a1b5309eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007c-0922000000-c4d248bec26d1bab5567View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007a-1901000000-7cf05f52d8f0260d6451View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001l-0917000000-9db7623321a85da36e23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0900000000-fa67d99e62ccd375ad9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-bdb7ef945c27ad9f9322View in MoNA
ChemSpider ID553044
ChEMBL IDCHEMBL86075
KEGG Compound IDNot Available
Pubchem Compound ID637429
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB40134
CRC / DFC (Dictionary of Food Compounds) IDMCW67-S:MCW67-S
EAFUS IDNot Available
Dr. Duke IDCALEBIN-A|4"-(3"-METHOXY-4"-HYDROXYPHENYL)-2"-OXO-3"-ENEBUTANYL-3-(3'-METHOXY-4'-HYDROXYPHENYL)-PROPENOATE
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
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti amyloid-betaDUKE
neuroprotective63726 Any compound that can be used for the treatment of neurodegenerative disorders.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Park SY, Kim DS: Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimer’s disease. J Nat Prod. 2002 Sep;65(9):1227-31. Pubmed [Isolation]
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).