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Showing Compound m-Coumaric acid (FDB002590)

Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2019-11-26 02:57:39 UTC
Primary IDFDB002590
Secondary Accession Numbers
  • FDB002591
Chemical Information
FooDB Namem-Coumaric acid
DescriptionCoumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. m-Coumaric acid is found in many foods, some of which are corn, garden tomato (variety), grape wine, and beer.
CAS Number588-30-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2E)-3-(3-Hydroxyphenyl)-2-propenoic acidChEBI
(2E)-3-(3-Hydroxyphenyl)acrylic acidChEBI
(e)-3-(3-Hydroxyphenyl)-2-propenoic acidChEBI
m-Hydroxycinnamic acidChEBI
trans-3-HydroxycinnamateChEBI
trans-3-Hydroxycinnamic acidChEBI
(2E)-3-(3-Hydroxyphenyl)prop-2-enoateKegg
(2E)-3-(3-Hydroxyphenyl)-2-propenoateGenerator
(2E)-3-(3-Hydroxyphenyl)acrylateGenerator
(e)-3-(3-Hydroxyphenyl)-2-propenoateGenerator
3-CoumarateGenerator
m-HydroxycinnamateGenerator
(2E)-3-(3-Hydroxyphenyl)prop-2-enoic acidGenerator
m-CoumarateGenerator
3'-HydroxycinnamateHMDB
3'-Hydroxycinnamic acidHMDB
3-(3-Hydroxyphenyl)-2-propenoateHMDB
3-(3-Hydroxyphenyl)-2-propenoic acidHMDB
3-(3-Hydroxyphenyl)acrylateHMDB
3-(3-Hydroxyphenyl)acrylsaeureHMDB
3-(3-Hydroxyphenyl)prop-2-enoateHMDB
3-(3-Hydroxyphenyl)prop-2-enoic acidHMDB
3-HydroxycinnamateHMDB
3-Hydroxycinnamic acidHMDB
m-Hydroxy-cinnamateHMDB
m-Hydroxy-cinnamic acidHMDB
3-Coumaric acid, (e)-isomerHMDB
Meta-coumaric acidHMDB
(e)-3-(3-Hydroxyphenyl)acrylic acidHMDB
(e)-3-Hydroxycinnamic acidHMDB
trans-3-(m-Hydroxyphenyl)-2-propenoic acidHMDB
trans-m-Coumaric acidHMDB
trans-m-Hydroxycinnamic acidHMDB
trans-3-CoumarateHMDB
(2e)-3-(3-Hydroxyphenyl)acrylateGenerator
3-(3-Hydroxyphenyl)acrylic acidHMDB
3-Coumaric acidChEBI
m-Coumaric aciddb_source
m-Cumaric aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility1.04 g/LALOGPS
logP1.71ALOGPS
logP1.83ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)4.01ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m³·mol⁻¹ChemAxon
Polarizability16.37 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H8O3
IUPAC name(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+
InChI KeyKKSDGJDHHZEWEP-SNAWJCMRSA-N
Isomeric SMILESOC(=O)\C=C\C1=CC=CC(O)=C1
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
Classification
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 65.85%; H 4.91%; O 29.24%DFC
    Melting PointNot Available
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-03xr-7900000000-61ee2ad0ad164a1f7550Spectrum
    GC-MSm-Coumaric acid, 2 TMS, GC-MS Spectrumsplash10-0udl-1691000000-331053d0d0b85549ac0bSpectrum
    GC-MSm-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-0udl-1691000000-331053d0d0b85549ac0bSpectrum
    GC-MSm-Coumaric acid, non-derivatized, GC-MS Spectrumsplash10-0udi-1891000000-049e1d80dd47b23e8c28Spectrum
    Predicted GC-MSm-Coumaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02t9-2900000000-91ffd4c10eaed6a17632Spectrum
    Predicted GC-MSm-Coumaric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00y3-6390000000-f1a30e2fb9cd1fb11341Spectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03xr-0900000000-4259219e89806dfe2602Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-014i-4900000000-2157a17ec65ead35585eSpectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00kf-9300000000-3325dd31a734dd4659bbSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-be33d196fbb525019f07Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-d256885fb0f35d3d6680Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-be33d196fbb525019f07Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0900000000-d256885fb0f35d3d6680Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-b5ad37fb931b464df7d5Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1900000000-c66c146ee9509bf8a413Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-9700000000-fcc332df0fcb818fe0e0Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-408ac0dd815354188750Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-146bae2da386ca2d4f1aSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-235b38f342376d1c9f90Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR SpectrumSpectrum
    2D NMR[1H,1H] 2D NMR SpectrumSpectrum
    2D NMR[1H,13C] 2D NMR SpectrumSpectrum
    ChemSpider ID553147
    ChEMBL IDCHEMBL98521
    KEGG Compound IDC12621
    Pubchem Compound ID637541
    Pubchem Substance IDNot Available
    ChEBI ID47925
    Phenol-Explorer ID463
    DrugBank IDNot Available
    HMDB IDHMDB01713
    CRC / DFC (Dictionary of Food Compounds) IDCMP64-S:CMP64-S
    EAFUS IDNot Available
    Dr. Duke IDM-COUMARIC-ACID
    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 IDCoumaric_acid
    Phenol-Explorer Metabolite ID463
    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
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
    — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).