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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:40:42 UTC
Update Date2022-03-07 02:56:28 UTC
HMDB IDHMDB0040134
Secondary Accession Numbers
  • HMDB40134
Metabolite Identification
Common 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.
Structure
Data?1563863495
Synonyms
ValueSource
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
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
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point138 - 139 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+194.94630932474
DeepCCS[M-H]-192.58830932474
DeepCCS[M-2H]-225.84430932474
DeepCCS[M+Na]+201.07330932474
AllCCS[M+H]+192.532859911
AllCCS[M+H-H2O]+189.732859911
AllCCS[M+NH4]+195.232859911
AllCCS[M+Na]+196.032859911
AllCCS[M-H]-191.732859911
AllCCS[M+Na-2H]-191.832859911
AllCCS[M+HCOO]-192.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Calebin ACOC1=C(O)C=CC(\C=C\C(=O)COC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=C16323.9Standard polar33892256
Calebin ACOC1=C(O)C=CC(\C=C\C(=O)COC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=C13493.1Standard non polar33892256
Calebin ACOC1=C(O)C=CC(\C=C\C(=O)COC(=O)\C=C\C2=CC(OC)=C(O)C=C2)=C13694.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Calebin A,1TMS,isomer #1COC1=CC(/C=C/C(=O)OCC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O3687.1Semi standard non polar33892256
Calebin A,1TMS,isomer #2COC1=CC(/C=C/C(=O)COC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O3688.5Semi standard non polar33892256
Calebin A,1TMS,isomer #3COC1=CC(/C=C/C(=O)OC=C(/C=C/C2=CC=C(O)C(OC)=C2)O[Si](C)(C)C)=CC=C1O3794.0Semi standard non polar33892256
Calebin A,2TMS,isomer #1COC1=CC(/C=C/C(=O)COC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C3705.6Semi standard non polar33892256
Calebin A,2TMS,isomer #2COC1=CC(/C=C/C(=O)OC=C(/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O3787.7Semi standard non polar33892256
Calebin A,2TMS,isomer #3COC1=CC(/C=C/C(=COC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O3788.5Semi standard non polar33892256
Calebin A,3TMS,isomer #1COC1=CC(/C=C/C(=O)OC=C(/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C3831.6Semi standard non polar33892256
Calebin A,3TMS,isomer #1COC1=CC(/C=C/C(=O)OC=C(/C=C/C2=CC=C(O[Si](C)(C)C)C(OC)=C2)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C3758.7Standard non polar33892256
Calebin A,1TBDMS,isomer #1COC1=CC(/C=C/C(=O)OCC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O3967.0Semi standard non polar33892256
Calebin A,1TBDMS,isomer #2COC1=CC(/C=C/C(=O)COC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O3968.7Semi standard non polar33892256
Calebin A,1TBDMS,isomer #3COC1=CC(/C=C/C(=O)OC=C(/C=C/C2=CC=C(O)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O4085.9Semi standard non polar33892256
Calebin A,2TBDMS,isomer #1COC1=CC(/C=C/C(=O)COC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)=CC=C1O[Si](C)(C)C(C)(C)C4237.0Semi standard non polar33892256
Calebin A,2TBDMS,isomer #2COC1=CC(/C=C/C(=O)OC=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O4335.7Semi standard non polar33892256
Calebin A,2TBDMS,isomer #3COC1=CC(/C=C/C(=COC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O4336.5Semi standard non polar33892256
Calebin A,3TBDMS,isomer #1COC1=CC(/C=C/C(=O)OC=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4545.4Semi standard non polar33892256
Calebin A,3TBDMS,isomer #1COC1=CC(/C=C/C(=O)OC=C(/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C4374.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Calebin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-0900000000-2ad529702fd246d705122017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calebin A GC-MS (2 TMS) - 70eV, Positivesplash10-03di-2180290000-22a6d9ea77f0e5ac9e3a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calebin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 10V, Positive-QTOFsplash10-00kr-0719000000-07ead4a60a17a1b5309e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 20V, Positive-QTOFsplash10-007c-0922000000-c4d248bec26d1bab55672017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 40V, Positive-QTOFsplash10-007a-1901000000-7cf05f52d8f0260d64512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 10V, Negative-QTOFsplash10-001l-0917000000-9db7623321a85da36e232017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 20V, Negative-QTOFsplash10-002f-0900000000-fa67d99e62ccd375ad9c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 40V, Negative-QTOFsplash10-004i-0900000000-bdb7ef945c27ad9f93222017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 10V, Positive-QTOFsplash10-000i-0209000000-795e17c72618a4b03df92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 20V, Positive-QTOFsplash10-0fg9-0926000000-108ab94e61601b9697e02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 40V, Positive-QTOFsplash10-002s-0901000000-300fea4fc07c65fe6d772021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 10V, Negative-QTOFsplash10-001i-0309000000-986d651772d992f360c52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 20V, Negative-QTOFsplash10-001j-0913000000-0a89845d9c4ce656ed092021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calebin A 40V, Negative-QTOFsplash10-000t-0900000000-3c192fce8e89b826b53e2021-09-22Wishart LabView Spectrum
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
FooDB IDFDB019830
KNApSAcK IDC00045250
Chemspider ID553044
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound637429
PDB IDNot Available
ChEBI ID175904
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .