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Record Information
Version3.6
Creation Date2005-11-20 22:13:20 UTC
Update Date2016-02-11 01:04:58 UTC
HMDB IDHMDB01713
Secondary Accession NumbersNone
Metabolite Identification
Common Namem-Coumaric acid
Descriptionm-Coumaric acid is a polyphenol metabolite from caffeic acid, formed by the gut microflora and the amount in human biofluids is diet-dependant. m-Coumaric acid is transported by the monocarboxylic acid transporter (MCT). MCT-mediated absorption of phenolic compounds per se and their colonic metabolites would exert significant impact on human health. (PMID 16870009 , 15479001 , 15479001 ).
Structure
Thumb
Synonyms
ValueSource
(2E)-3-(3-Hydroxyphenyl)-2-propenoic acidChEBI
(2E)-3-(3-Hydroxyphenyl)acrylic acidChEBI
(e)-3-(3-Hydroxyphenyl)-2-propenoic acidChEBI
3-Coumaric acidChEBI
m-Coumaric acidChEBI
m-Hydroxycinnamic acidChEBI
trans-3-HydroxycinnamateChEBI
trans-3-Hydroxycinnamic acidChEBI
(2E)-3-(3-Hydroxyphenyl)-2-propenoateGenerator
(e)-3-(3-Hydroxyphenyl)prop-2-enoateGenerator
(2E)-3-(3-Hydroxyphenyl)acrylateGenerator
(e)-3-(3-Hydroxyphenyl)-2-propenoateGenerator
3-CoumarateGenerator
m-CoumarateGenerator
m-HydroxycinnamateGenerator
(2E)-3-(3-Hydroxyphenyl)prop-2-enoateHMDB
(2E)-3-(3-Hydroxyphenyl)prop-2-enoic acidHMDB
3'-HydroxycinnamateHMDB
3'-Hydroxycinnamic acidHMDB
3-(3-Hydroxyphenyl)-2-propenoateHMDB
3-(3-Hydroxyphenyl)-2-propenoic acidHMDB
3-(3-Hydroxyphenyl)acrylateHMDB
3-(3-Hydroxyphenyl)acrylic acidHMDB
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
trans-3-Coumaric acidHMDB
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=CC(O)=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 KeyInChIKey=KKSDGJDHHZEWEP-SNAWJCMRSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxycinnamic acids. These 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
  • Hydroxycinnamic acid
  • Coumaric acid or derivatives
  • Coumaric acid
  • Cinnamic acid
  • Phenylpropene
  • Styrene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and 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
Water Solubility1.04 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.04 m3·mol-1ChemAxon
Polarizability16.37 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
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
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
MSMass Spectrum (Electron Ionization)splash10-03xr-7900000000-61ee2ad0ad164a1f7550View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.022 +/- 0.009 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.014 +/- 0.006 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.046 +/- 0.012 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.051 +/- 0.017 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.012 +/- 0.006 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.007 +/- 0.002 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.008 +/- 0.002 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.881 +/- 0.878 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified2.0103 +/- 0.548 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified2.0712 +/- 0.426 nmol/g of fecesAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified11.192 +/- 7.46 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 463
  • Not Applicable
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.032 +/- 0.059 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.078 +/- 0.085 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.052 +/- 0.065 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.092 +/- 0.092 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.17 +/- 0.15 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.019 +/- 0.013 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.013 +/- 0.0065 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.012 +/- 0.003 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified18.808 +/- 9.712 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified6.345 +/- 5.041 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID463
Phenol Explorer Metabolite ID463
FoodDB IDFDB002590
KNApSAcK IDNot Available
Chemspider ID553147
KEGG Compound IDC12621
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01713
Metagene LinkHMDB01713
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)Download (PDF)
General References
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