ChemFOnt: Showing chemical card for 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid (CFc000041534)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:43:35 UTC

Chemfont ID

CFc000041534

Molecule Identification

Common Name

3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid

Definition

3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid (CMPF) is also called 3-carboxy-4-methyl-5-propyl-2-furanpropanoic acid and 2-(2-carboxyethyl)-4-methyl-4-propylfuran-3-carboxylic acid. CMPF is significantly accumulated in the serum of chronic kidney disease patients and is considered to be a potent uremic toxin (PMID: 8734460 ) and identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821 ). There are several minor derivatives of CMPF that have been detected in serum and urine including 3-carboxy-4-methyl-5-pentyl-2-furanpropionic acid, 3-carboxy-4-methyl-5-ethyl-2-furanpropionic acid, and 3-carboxy-5-propyl-2-furanpropionic acid. CMPF was first detected in human urine in 1979 (PMID: 12388676 ) and it is believed to be formed from the consumption of fish, vegetables, and fruits (PMID: 19083276 ">19083276 ; PMID: 12388676 ). CMPF is a strong inhibitor of mitochondrial respiration and is associated with thyroid dysfunction (PMID: 19083276 ). CMPF also directly inhibits renal secretion of various drugs and endogenous organic acids by competitively inhibiting OAT3 transporters (PMID: 11967025 ). It is also thought to contribute to various neurological abnormalities because it inhibits the transport of organic acids at the blood-brain barrier (PMID: 12388676 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
CMPF	ChEBI
3-Carboxy-4-methyl-5-propyl-2-furanpropionate	Generator
3-Carboxy-4-methyl-5-propyl-2-furan-propanoate	HMDB
U(3,3)	HMDB
CMPFPA	HMDB
3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid	HMDB
Propylurofuranic acid	HMDB
3-Carboxy-4-methyl-5-propyl-2-furanpropanoate	HMDB
2-(2-Carboxyethyl)-4-methyl-4-propylfuran-3-carboxylic acid	HMDB
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid	HMDB, ChEBI

Chemical Formula

C₁₂H₁₆O₅

Average Molecular Weight

240.2524

Monoisotopic Molecular Weight

240.099773622

IUPAC Name

2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid

Traditional Name

2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid

CAS Registry Number

86879-39-2

SMILES

CCCC1=C(C)C(C(O)=O)=C(CCC(O)=O)O1

InChI Identifier

InChI=1S/C12H16O5/c1-3-4-8-7(2)11(12(15)16)9(17-8)5-6-10(13)14/h3-6H2,1-2H3,(H,13,14)(H,15,16)

InChI Key

WMCQWXZMVIETAO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Furanoid fatty acids

Alternative Parents

Substituents

Furanoid fatty acid
Furoic acid or derivatives
Furan-3-carboxylic acid
Furan-3-carboxylic acid or derivatives
Furoic acid
Dicarboxylic acid or derivatives
Furan
Heteroaromatic compound
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:41254 )
furoic acid (CHEBI:41254 )
Heterocyclic fatty acids (LMFA01150004 )

Functional Ontology

Physiological effect

Health effect

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Liver damage (PMID: 31434538)

Nervous system disorder

Nerve damage (PMID: 31434538)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20090676)

Organ

Placenta (HMDB: HMDB0061112)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)
Urine (PMID: 27510537)

Cellular substructure

Membrane (HMDB: HMDB0061112)

Source

Exogenous

Exogenous (HMDB: HMDB0061112)

Process

Not Available

Role

Biological role

Human metabolite (HMDB: HMDB0061112)
Waste product (PMID: 35448883)

Indirect biological role

Metabotoxin

Uremic toxin (HMDB: HMDB0061112)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	1.68	ALOGPS
logP	2.3	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.74 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	61.08 m³·mol⁻¹	ChemAxon
Polarizability	25.26 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

HMDB0061112

DrugBank ID

DB07517

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB093609

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

123979

PDB ID

Not Available

ChEBI ID

41254

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid (CFc000041534)

MOL for CFc000041534 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

3D MOL for CFc000041534 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

3D SDF for CFc000041534 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

3D-SDF for CFc000041534 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

PDB for CFc000041534 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

3D PDB for CFc000041534 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

SMILES for CFc000041534 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

INCHI for CFc000041534 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

Structure for CFc000041534 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

3D Structure for CFc000041534 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)