Human Metabolome Database: Showing metabocard for m-Coumaric acid (HMDB0001713)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

4.0

Status

Detected and Quantified

Creation Date

2005-11-20 22:13:20 UTC

Update Date

2020-02-26 21:23:31 UTC

HMDB ID

HMDB0001713

Secondary Accession Numbers

HMDB0062774
HMDB01713
HMDB62774

Metabolite Identification

Common Name

m-Coumaric acid

Description

m-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 is an extremely weak basic (essentially neutral) compound (based on its pKa). m-Coumaric acid exists in all living organisms, ranging from bacteria to humans. m-Coumaric acid (CAS: 588-30-7) is a polyphenol metabolite from caffeic acid, formed by the gut microflora. Outside of the human body, m-Coumaric acid is found, on average, in the highest concentration within a few different foods, such as olives, corns, and beers. m-Coumaric acid has also been detected, but not quantified in, several different foods, such as carrots, strawberries, grape wines, garden tomato (var.), and bilberries. This could make m-coumaric acid a potential biomarker for the consumption of these foods. MCT-mediated absorption of phenolic compounds per se and their colonic metabolites would exert a significant impact on human health (PMID: 16870009 , 15479001 , 15479001 ). m-Coumaric acid is transported by the monocarboxylic acid transporter (MCT). The amount of this compound in human biofluids is diet-dependant. m-Coumaric acid is detected after the consumption of whole grain.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2E)-3-(3-Hydroxyphenyl)-2-propenoic acid	ChEBI
(2E)-3-(3-Hydroxyphenyl)acrylic acid	ChEBI
(e)-3-(3-Hydroxyphenyl)-2-propenoic acid	ChEBI
3-Coumaric acid	ChEBI
m-Hydroxycinnamic acid	ChEBI
trans-3-Hydroxycinnamate	ChEBI
trans-3-Hydroxycinnamic acid	ChEBI
(2E)-3-(3-Hydroxyphenyl)prop-2-enoate	Kegg
(2E)-3-(3-Hydroxyphenyl)-2-propenoate	Generator
(2E)-3-(3-Hydroxyphenyl)acrylate	Generator
(e)-3-(3-Hydroxyphenyl)-2-propenoate	Generator
3-Coumarate	Generator
m-Hydroxycinnamate	Generator
(2E)-3-(3-Hydroxyphenyl)prop-2-enoic acid	Generator
m-Coumarate	Generator
3'-Hydroxycinnamate	HMDB
3'-Hydroxycinnamic acid	HMDB
3-(3-Hydroxyphenyl)-2-propenoate	HMDB
3-(3-Hydroxyphenyl)-2-propenoic acid	HMDB
3-(3-Hydroxyphenyl)acrylate	HMDB
3-(3-Hydroxyphenyl)acrylic acid	HMDB
3-(3-Hydroxyphenyl)acrylsaeure	HMDB
3-(3-Hydroxyphenyl)prop-2-enoate	HMDB
3-(3-Hydroxyphenyl)prop-2-enoic acid	HMDB
3-Hydroxycinnamate	HMDB
3-Hydroxycinnamic acid	HMDB
m-Hydroxy-cinnamate	HMDB
m-Hydroxy-cinnamic acid	HMDB
trans-3-Coumaric acid	HMDB
3-Coumaric acid, (e)-isomer	HMDB
Meta-coumaric acid	HMDB
(e)-3-(3-Hydroxyphenyl)acrylic acid	HMDB
(e)-3-Hydroxycinnamic acid	HMDB
trans-3-(m-Hydroxyphenyl)-2-propenoic acid	HMDB
trans-m-Coumaric acid	HMDB
trans-m-Hydroxycinnamic acid	HMDB
m-Coumaric acid	HMDB
trans-3-Coumarate	HMDB

Chemical Formula

C₉H₈O₃

Average Molecular Weight

164.158

Monoisotopic Molecular Weight

164.047344122

IUPAC Name

(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid

Traditional Name

m-coumaric acid

CAS Registry Number

14755-02-3

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 Key

KKSDGJDHHZEWEP-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

3-coumaric acid (CHEBI:32357 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Plant:

Poaceae

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	192 - 194 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.04 g/L	ALOGPS
logP	1.71	ALOGPS
logP	1.83	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.01	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.04 m³·mol⁻¹	ChemAxon
Polarizability	16.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udl-1691000000-331053d0d0b85549ac0b	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udl-1691000000-331053d0d0b85549ac0b	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-1891000000-049e1d80dd47b23e8c28	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02t9-2900000000-91ffd4c10eaed6a17632	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00y3-6390000000-f1a30e2fb9cd1fb11341	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-03xr-0900000000-4259219e89806dfe2602	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-014i-4900000000-2157a17ec65ead35585e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00kf-9300000000-3325dd31a734dd4659bb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-03di-0900000000-be33d196fbb525019f07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0002-0900000000-d256885fb0f35d3d6680	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03di-0900000000-be33d196fbb525019f07	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0002-0900000000-d256885fb0f35d3d6680	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0900000000-b5ad37fb931b464df7d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-1900000000-c66c146ee9509bf8a413	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvi-9700000000-fcc332df0fcb818fe0e0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-408ac0dd815354188750	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-146bae2da386ca2d4f1a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014m-3900000000-235b38f342376d1c9f90	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03xr-7900000000-61ee2ad0ad164a1f7550	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.022 +/- 0.009 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.014 +/- 0.006 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.046 +/- 0.012 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.051 +/- 0.017 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.012 +/- 0.006 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.007 +/- 0.002 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.008 +/- 0.002 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	0.881 +/- 0.878 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	12771321	details
Blood	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	16197573	details
Blood	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	19671472	details
Blood	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	19333587	details
Blood	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	20222713	details
Blood	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	15309457	details
Blood	Expected but not Quantified		Not Available	Not Available	Normal		details
Blood	Detected and Quantified	0-3.4 uM	Adult (>18 years old)	Both	Normal	19812218	details
Feces	Detected but not Quantified		Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified		Not Specified	Both	Normal	25486321	details
Feces	Detected and Quantified	2.0103 +/- 0.548 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	2.0712 +/- 0.426 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	0.201 (0.0305-1.0843) nmol/g wet feces	Adult (>18 years old)	Both	Normal	28029051	details
Urine	Detected and Quantified	11.192 +/- 7.46 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	0.270 +/- 0.620 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	0.360 +/- 0.873 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	12771321	details
Urine	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	16197573	details
Urine	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	19671472	details
Urine	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	19333587	details
Urine	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	20222713	details
Urine	Expected but not Quantified		Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 463	15309457	details
Urine	Detected but not Quantified		Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	0.032 +/- 0.059 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.078 +/- 0.085 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.052 +/- 0.065 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.092 +/- 0.092 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.17 +/- 0.15 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.019 +/- 0.013 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.013 +/- 0.0065 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	0.148 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.251 +/- 0.409 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected and Quantified	0.012 +/- 0.003 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	18.808 +/- 9.712 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details
Urine	Detected and Quantified	6.345 +/- 5.041 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Mordechai, Hien, ...	details

Associated Disorders and Diseases

Disease References

Eosinophilic esophagitis
(). Mordechai, Hien, and David S. Wishart. .

Associated OMIM IDs

610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

463

FoodDB ID

FDB002590

KNApSAcK ID

Not Available

Chemspider ID

553147

KEGG Compound ID

C12621

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

M-coumaric_acid

METLIN ID

305

PubChem Compound

637541

PDB ID

Not Available

ChEBI ID

32357

Food Biomarker Ontology

Not Available

VMH ID

Not Available

References

Synthesis Reference

Neish, 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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Colen CB, Seraji-Bozorgzad N, Marples B, Galloway MP, Sloan AE, Mathupala SP: Metabolic remodeling of malignant gliomas for enhanced sensitization during radiotherapy: an in vitro study. Neurosurgery. 2006 Dec;59(6):1313-23; discussion 1323-4. [PubMed:17277695 ]
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Funk C, Braune A, Grabber JH, Steinhart H, Bunzel M: Moderate ferulate and diferulate levels do not impede maize cell wall degradation by human intestinal microbiota. J Agric Food Chem. 2007 Mar 21;55(6):2418-23. Epub 2007 Feb 24. [PubMed:17319685 ]
Grande MJ, Lopez RL, Abriouel H, Valdivia E, Ben Omar N, Maqueda M, Martinez-Canamero M, Galvez A: Treatment of vegetable sauces with enterocin AS-48 alone or in combination with phenolic compounds to inhibit proliferation of Staphylococcus aureus. J Food Prot. 2007 Feb;70(2):405-11. [PubMed:17340876 ]
Ibanez AJ, Muck A, Svatos A: Dissipation of charge on MALDI-TOF polymeric chips using an electron-acceptor: analysis of proteins. J Mass Spectrom. 2007 May;42(5):634-40. [PubMed:17370249 ]
Efdi M, Itoh T, Akao Y, Nozawa Y, Koketsu M, Ishihara H: The isolation of secondary metabolites and in vitro potent anti-cancer activity of clerodermic acid from Enicosanthum membranifolium. Bioorg Med Chem. 2007 Jun 1;15(11):3667-71. Epub 2007 Mar 18. [PubMed:17400462 ]
Azzini E, Bugianesi R, Romano F, Di Venere D, Miccadei S, Durazzo A, Foddai MS, Catasta G, Linsalata V, Maiani G: Absorption and metabolism of bioactive molecules after oral consumption of cooked edible heads of Cynara scolymus L. (cultivar Violetto di Provenza) in human subjects: a pilot study. Br J Nutr. 2007 May;97(5):963-9. [PubMed:17408528 ]
Appiah-Opong R, Commandeur JN, van Vugt-Lussenburg B, Vermeulen NP: Inhibition of human recombinant cytochrome P450s by curcumin and curcumin decomposition products. Toxicology. 2007 Jun 3;235(1-2):83-91. Epub 2007 Mar 15. [PubMed:17433521 ]
Wang Q, Morris ME: The role of monocarboxylate transporter 2 and 4 in the transport of gamma-hydroxybutyric acid in mammalian cells. Drug Metab Dispos. 2007 Aug;35(8):1393-9. Epub 2007 May 14. [PubMed:17502341 ]
Keyhanian S, Stahl-Biskup E: Phenolic constituents in dried flowers of aloe vera (Aloe barbadensis) and their in vitro antioxidative capacity. Planta Med. 2007 Jun;73(6):599-602. Epub 2007 May 22. [PubMed:17520524 ]
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Henry BL, Monien BH, Bock PE, Desai UR: A novel allosteric pathway of thrombin inhibition: Exosite II mediated potent inhibition of thrombin by chemo-enzymatic, sulfated dehydropolymers of 4-hydroxycinnamic acids. J Biol Chem. 2007 Nov 2;282(44):31891-9. Epub 2007 Sep 5. [PubMed:17804413 ]
Qin J, Chen D, Hu H, Qiao M, Zhao X, Chen B: Body distributioin of RGD-mediated liposome in brain-targeting drug delivery. Yakugaku Zasshi. 2007 Sep;127(9):1497-501. [PubMed:17827930 ]
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Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

m-Coumaric acid → 6-{3-[(1E)-2-carboxyeth-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details
m-Coumaric acid → 3,4,5-trihydroxy-6-{[(2E)-3-(3-hydroxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

m-Coumaric acid → (2E)-3-[3-(sulfooxy)phenyl]prop-2-enoic acid	details

Showing metabocard for m-Coumaric acid (HMDB0001713)

Structure for HMDB0001713 (m-Coumaric acid)

Enzymes

Reactions

Reactions