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Showing Compound L-Malic acid caffeate (FDB000379)

Record Information
Version1.0
Creation date2010-04-08 22:04:33 UTC
Update date2020-02-24 19:10:06 UTC
Primary IDFDB000379
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Malic acid caffeate
DescriptionCaffeoylmalic acid, also known as caffeoylmalate, 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. Caffeoylmalic acid has been detected, but not quantified in, several different foods, such as radishes (Raphanus sativus), pears (Pyrus communis), herbs and spices, herbal tea, and black tea. This could make caffeoylmalic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Caffeoylmalic acid.
CAS Number53755-04-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
CaffeoylmalateGenerator
(S)-Phaselic acidHMDB
Phaseolic acid?HMDB
2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioateGenerator
Caffeoylmalic acidMeSH
L-Malate caffeateGenerator
L-Malic acid caffeic acidGenerator
Caffeoyl-L-malic acidmanual
L-Malic acid caffeatemanual
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP1.87ALOGPS
logP1.31ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.07ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area141.36 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity68.4 m³·mol⁻¹ChemAxon
Polarizability26.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H12O8
IUPAC name2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
InChI IdentifierInChI=1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)/b4-2+
InChI KeyPMKQSEYPLQIEAY-DUXPYHPUSA-N
Isomeric SMILESOC(=O)CC(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O
Average Molecular Weight296.2296
Monoisotopic Molecular Weight296.05321736
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
  • Tricarboxylic acid or derivatives
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.71%; H 4.08%; O 43.21%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +28.3 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSL-Malic acid caffeate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-1910000000-74e3c09316c8d9fb3ea5Spectrum
Predicted GC-MSL-Malic acid caffeate, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0avi-4146190000-5a765f56e5efd99345a3Spectrum
Predicted GC-MSL-Malic acid caffeate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0401-1790000000-ef531f4b3f8db4d508cb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xr-3940000000-ff40fcbd1f957b9e680e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dr-7900000000-187b75c221f4f3c49fff2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ftb-1970000000-6b43ca38ba19571e6a672016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00bi-3920000000-98c6d2f5b48eb1a9ccc32016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03g0-3900000000-60d5ea04840a20f30f6b2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0290000000-a44daa816456bebdbd8a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9540000000-6be49add441a49df34b92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3910000000-46381cd1c0d16863ebb52021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0920000000-a4c71d6efa8a850a8ec62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-ecf10995634e427e58a92021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1900000000-ca91bf87f1f063f2269a2021-09-24View Spectrum
NMRNot Available
ChemSpider ID4816367
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6124299
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29318
CRC / DFC (Dictionary of Food Compounds) IDDCG74-V:BBN70-X
EAFUS IDNot Available
Dr. Duke IDPHASEOLIC-ACID
BIGG IDNot Available
KNApSAcK IDC00002765
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).