ChemFOnt: Showing chemical card for 3-(3-Hydroxyphenyl)propanoic acid (CFc000000274)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:37 UTC

Chemfont ID

CFc000000274

Molecule Identification

Common Name

3-(3-Hydroxyphenyl)propanoic acid

Definition

3-(3-Hydroxyphenyl)propanoic (hMPP) acid is one of the major metabolites of ingested caffeic acid (PMID: 15479001 ) and of the phenolic degradation products of proanthocyanidins (the most abundant polyphenol present in chocolate) by the microflora in the colon (PMID: 12663291 ). mHPP is suspected to have antioxidants properties and is actively absorbed by the monocarboxylic acid transporter (MCT) in intestinal Caco-2 cell monolayers (PMID: 15479001 , 12663291 ). hMPP has been found to be a metabolite of Clostridium, Escherichia, and Eubacterium (PMID: 28393285 , 19520845 ). 3-(3-Hydroxyphenyl)propanoic acid is a flavonoid metabolite. 3-(3-Hydroxyphenyl)propanoic acid is a phenolic acid metabolite formed by the gut microflora detected after the consumption of whole grain.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(3-Hydroxy-phenyl)-propanoic acid	ChEBI
3-(m-Hydroxyphenyl)propionic acid	ChEBI
beta-(m-Hydroxyphenyl)propionic acid	ChEBI
Dihydro-3-coumaric acid	ChEBI
3-Hydroxyphenylpropanoate	Kegg
3-(3-Hydroxyphenyl)propanoate	Kegg
3-(3-Hydroxy-phenyl)-propanoate	Generator
3-(3-Hydroxyphenyl)propionate	Generator
3-(m-Hydroxyphenyl)propionate	Generator
b-(m-Hydroxyphenyl)propionate	Generator
b-(m-Hydroxyphenyl)propionic acid	Generator
beta-(m-Hydroxyphenyl)propionate	Generator
Β-(m-hydroxyphenyl)propionate	Generator
Β-(m-hydroxyphenyl)propionic acid	Generator
Dihydro-3-coumarate	Generator
3-Hydroxyphenylpropanoic acid	Generator
3-(3-Hydroxy-phenyl)-propionic acid	HMDB
3-Hydroxybenzenepropanoate	HMDB
3-Hydroxybenzenepropanoic acid	HMDB
3-Hydroxydihydrocinnamate	HMDB
3-Hydroxydihydrocinnamic acid	HMDB
3-Hydroxyhydrocinnamic acid	HMDB
3-Hydroxyphenylpropionate	HMDB
3-Hydroxyphenylpropionic acid	HMDB
b-(3-Hydroxyphenyl)propionate	HMDB
b-(3-Hydroxyphenyl)propionic acid	HMDB
beta-(3-Hydroxyphenyl)propionate	HMDB
beta-(3-Hydroxyphenyl)propionic acid	HMDB
dihydro-m-Coumarate	HMDB
dihydro-m-Coumaric acid	HMDB, MeSH
m-Hydrocoumaric acid	HMDB
m-Hydroxy-hydrocinnamate	HMDB
m-Hydroxy-hydrocinnamic acid	HMDB
m-Hydroxyphenylpropionate	HMDB
m-Hydroxyphenylpropionic acid	HMDB, MeSH
dihydro-3-Coumaric acid, monosodium salt	MeSH, HMDB
3-(3'-Hydroxyphenyl)propanoic acid	HMDB
3-(3-Hydroxyphenyl)propanoic acid	HMDB

Chemical Formula

C₉H₁₀O₃

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

IUPAC Name

3-(3-hydroxyphenyl)propanoic acid

Traditional Name

3-hydroxyphenylpropionic acid

CAS Registry Number

621-54-5

SMILES

OC(=O)CCC1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C9H10O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-3,6,10H,4-5H2,(H,11,12)

InChI Key

QVWAEZJXDYOKEH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:1427 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 19671472)

Excreta

Biofluid or Excreta

Urine (PMID: 15315398)
Feces (PMID: 24010549)

Source

Exogenous

Exogenous (HMDB: HMDB0000375)

Food

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0000375)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0000375)

Tea

Tea products (HMDB: HMDB0000375)

Fat and oil

Olive oil (HMDB: HMDB0000375)

Fruit

Fruits (HMDB: HMDB0000375)

Vegetable

Vegetables (HMDB: HMDB0000375)

Legumes (HMDB: HMDB0000375)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0000375)

Nut

Nuts (HMDB: HMDB0000375)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0000375)

Endogenous

Plant

Plant (HMDB: HMDB0000375)

Microbe

Microbe (HMDB: HMDB0000375)
Escherichia coli (HMDB: HMDB0000375)
Eubacterium oxidoreducens (HMDB: HMDB0000375)

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

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.8 g/L	ALOGPS
logP	1.14	ALOGPS
logP	1.75	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	4.21	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	3	ChemAxon
Refractivity	43.95 m³·mol⁻¹	ChemAxon
Polarizability	16.92 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

HMDB0000375

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021993

KNApSAcK ID

C00052683

Chemspider ID

KEGG Compound ID

C11457

BioCyc ID

3-HYDROXYPHENYL-PROPIONATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

PDB ID

Not Available

ChEBI ID

1427

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Dombrow, M.; Linnell, W. H. Preparation of m-hydroxyphenylpropionic acid. Journal of Pharmacy and Pharmacology (1952), 4 118-19.

Showing chemical card for 3-(3-Hydroxyphenyl)propanoic acid (CFc000000274)

MOL for CFc000000274 (3-(3-Hydroxyphenyl)propanoic acid)

3D MOL for CFc000000274 (3-(3-Hydroxyphenyl)propanoic acid)

3D SDF for CFc000000274 (3-(3-Hydroxyphenyl)propanoic acid)

3D-SDF for CFc000000274 (3-(3-Hydroxyphenyl)propanoic acid)

PDB for CFc000000274 (3-(3-Hydroxyphenyl)propanoic acid)

3D PDB for CFc000000274 (3-(3-Hydroxyphenyl)propanoic acid)

SMILES for CFc000000274 (3-(3-Hydroxyphenyl)propanoic acid)

INCHI for CFc000000274 (3-(3-Hydroxyphenyl)propanoic acid)

Structure for CFc000000274 (3-(3-Hydroxyphenyl)propanoic acid)

3D Structure for CFc000000274 (3-(3-Hydroxyphenyl)propanoic acid)