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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:40:42 UTC
Update Date2019-07-23 06:31:35 UTC
HMDB IDHMDB0040134
Secondary Accession Numbers
  • HMDB40134
Metabolite Identification
Common NameCalebin A
DescriptionCalebin A is found in herbs and spices. Calebin A is a constituent of the rhizomes of Cucuma longa (turmeric).
Structure
Data?1563863495
Synonyms
ValueSource
Calebin-aChEMBL
4''-(3'''-methoxy-4'''-hydroxyphenyl)-2''-oxo-3''-enebutanyl 3-(3'-methoxy-4'-hydroxyphenyl)propenoateHMDB
Chemical FormulaC21H20O7
Average Molecular Weight384.3793
Monoisotopic Molecular Weight384.120902994
IUPAC Name(3E)-4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-en-1-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Traditional Name(3E)-4-(4-hydroxy-3-methoxyphenyl)-2-oxobut-3-en-1-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(\C=C\C(=O)COC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=C1
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound 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
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Methoxyphenol
  • Phenylpropene
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Anisole
  • Alpha-acyloxy ketone
  • Phenol
  • Fatty acid ester
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated ketone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Enone
  • Acryloyl-group
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point138 - 139 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0900000000-2ad529702fd246d70512JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2180290000-22a6d9ea77f0e5ac9e3aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0719000000-07ead4a60a17a1b5309eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007c-0922000000-c4d248bec26d1bab5567JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007a-1901000000-7cf05f52d8f0260d6451JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001l-0917000000-9db7623321a85da36e23JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-0900000000-fa67d99e62ccd375ad9cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-bdb7ef945c27ad9f9322JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
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 IDNot Available
FoodDB IDFDB019830
KNApSAcK IDNot Available
Chemspider ID553044
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound637429
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  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:12350137 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .