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Showing Compound Calebin A (FDB019830)

Record Information
Version1.0
Creation date2010-04-08 22:14:37 UTC
Update date2019-11-26 03:17:54 UTC
Primary IDFDB019830
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCalebin A
DescriptionCalebin A 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. Calebin A has been detected, but not quantified in, herbs and spices and turmerics (Curcuma longa). This could make calebin a a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Calebin A.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCalebin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-0900000000-2ad529702fd246d70512Spectrum
Predicted GC-MSCalebin A, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-2180290000-22a6d9ea77f0e5ac9e3aSpectrum
Predicted GC-MSCalebin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0719000000-07ead4a60a17a1b5309e2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007c-0922000000-c4d248bec26d1bab55672017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007a-1901000000-7cf05f52d8f0260d64512017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001l-0917000000-9db7623321a85da36e232017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0900000000-fa67d99e62ccd375ad9c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-bdb7ef945c27ad9f93222017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0209000000-795e17c72618a4b03df92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fg9-0926000000-108ab94e61601b9697e02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002s-0901000000-300fea4fc07c65fe6d772021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0309000000-986d651772d992f360c52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-0913000000-0a89845d9c4ce656ed092021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-0900000000-3c192fce8e89b826b53e2021-09-22View Spectrum
NMRNot Available
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
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).