Showing metabocard for m-Coumaric acid (BMDB0001713)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:57 UTC
Update Date2020-04-22 15:08:48 UTC
BMDB IDBMDB0001713
Secondary Accession Numbers
  • BMDB01713
Metabolite Identification
Common Namem-Coumaric acid
Descriptionm-Coumaric acid, also known as 3-coumarate, 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. m-Coumaric acid exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on m-Coumaric acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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)-isomerMeSH, HMDB
Meta-coumaric acidMeSH, HMDB
(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
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid
Traditional Namem-coumaric acid
CAS Registry Number588-30-7
SMILES
OC(=O)\C=C\C1=CC(O)=CC=C1
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point192 - 194 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udl-1691000000-331053d0d0b85549ac0bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udl-1691000000-331053d0d0b85549ac0bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-1891000000-049e1d80dd47b23e8c28View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02t9-2900000000-91ffd4c10eaed6a17632View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00y3-6390000000-f1a30e2fb9cd1fb11341View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03xr-0900000000-4259219e89806dfe2602View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-014i-4900000000-2157a17ec65ead35585eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00kf-9300000000-3325dd31a734dd4659bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-be33d196fbb525019f07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-0002-0900000000-d256885fb0f35d3d6680View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-be33d196fbb525019f07View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0002-0900000000-d256885fb0f35d3d6680View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-1900000000-87be0242c9f5b426f6b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-9e4128fa078e73e71cbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-0900000000-d256885fb0f35d3d6680View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9100000000-1865c168df491277a4d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0006-9000000000-296d14129321002679a3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00kf-9700000000-6d29cdde66b32806de5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-9da76da83e0462c48acfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-bf33c5b8f5901c60b332View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-2900000000-11ae76e2fe36da1dfbe6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-b6bf0b46b2fa8324cf71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00kb-0900000000-1065251e7cf92f343533View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004i-9000000000-0a87c81608b3fbcee7c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-b5ad37fb931b464df7d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1900000000-c66c146ee9509bf8a413View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-9700000000-fcc332df0fcb818fe0e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-408ac0dd815354188750View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-146bae2da386ca2d4f1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014m-3900000000-235b38f342376d1c9f90View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03xr-7900000000-61ee2ad0ad164a1f7550View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001713
DrugBank IDNot Available
Phenol Explorer Compound ID463
FooDB IDFDB002590
KNApSAcK IDC00052344
Chemspider ID553147
KEGG Compound IDC12621
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkM-coumaric_acid
METLIN ID305
PubChem Compound637541
PDB IDNot Available
ChEBI ID32357
References
Synthesis ReferenceNeish, A. C. Formation of m- and p-coumaric acids by enzymic deamination of the corresponding isomers of tyrosine. Phytochemistry (Elsevier) (1961), 1 1-24.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available