ChemFOnt: Showing chemical card for m-Coumaric acid (CFc000001213)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:48 UTC

Chemfont ID

CFc000001213

Molecule Identification

Common Name

m-Coumaric acid

Definition

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 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, and bilberries. 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
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)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
3-Coumaric acid, (e)-isomer	MeSH, HMDB
Meta-coumaric acid	MeSH, 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
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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12771321)

Excreta

Biofluid or Excreta

Urine (PMID: 16197573)
Feces (PMID: 24010549)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001713)

Source

Endogenous

Endogenous (HMDB: HMDB0001713)

Plant

Plant (HMDB: HMDB0001713)
Poaceae (HMDB: HMDB0001713)

Exogenous

Food

Food (HMDB: HMDB0001713)
Legumes (HMDB: HMDB0001713)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Beverage

Fermented beverage

Alcoholic beverage

Red wine (HMDB: HMDB0001713)

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Berry

Fruits (HMDB: HMDB0001713)

Vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Spinach (FooDB: FOOD00178)

Root vegetable

Carrot (FooDB: FOOD00245)

Vegetables (HMDB: HMDB0001713)

Fruit vegetable

Olive (FooDB: FOOD00121)
Garden tomato (var.) (FooDB: FOOD00173)

Coffee and coffee product

Coffee

Coffee product

Coffee products (HMDB: HMDB0001713)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Cereal product

Whole grain cereal products (HMDB: HMDB0001713)

Leavened bread

Rye bread (FooDB: FOOD00809)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0001713)

Tea

Tea products (HMDB: HMDB0001713)

Fat and oil

Olive oil (HMDB: HMDB0001713)

Nut

Nuts (HMDB: HMDB0001713)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

2-Oxopent-4-enoate Metabolism (PathBank: SMP0122102)
2-Oxopent-4-enoate Metabolism 2 (PathBank: SMP0122224)

Role

Industrial application

Pharmaceutical industry

Biomarker

Fruits Consumption (MarkerDB: MDB00000341)
Vegetables Consumption (MarkerDB: MDB00000341)
Apple Consumption (MarkerDB: MDB00000341)
Peach Consumption (MarkerDB: MDB00000341)
Berries Consumption (MarkerDB: MDB00000341)
Fruit Juices Consumption (MarkerDB: MDB00000341)
Onion Consumption (MarkerDB: MDB00000341)
Black Tea Consumption (MarkerDB: MDB00000341)
Herbal Tea Consumption (MarkerDB: MDB00000341)
Chocolate Consumption (MarkerDB: MDB00000341)
Wine Consumption (MarkerDB: MDB00000341)
Citrus Fruits Consumption (MarkerDB: MDB00000341)
Grapefruit Consumption (MarkerDB: MDB00000341)
Grapefruit Juice Consumption (MarkerDB: MDB00000341)
Orange Consumption (MarkerDB: MDB00000341)
Orange Juice Consumption (MarkerDB: MDB00000341)

Physical Properties

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

External Links

HMDB ID

HMDB0001713

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

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

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.

Showing chemical card for m-Coumaric acid (CFc000001213)

MOL for CFc000001213 (m-Coumaric acid)

3D MOL for CFc000001213 (m-Coumaric acid)

3D SDF for CFc000001213 (m-Coumaric acid)

3D-SDF for CFc000001213 (m-Coumaric acid)

PDB for CFc000001213 (m-Coumaric acid)

3D PDB for CFc000001213 (m-Coumaric acid)

SMILES for CFc000001213 (m-Coumaric acid)

INCHI for CFc000001213 (m-Coumaric acid)

Structure for CFc000001213 (m-Coumaric acid)

3D Structure for CFc000001213 (m-Coumaric acid)