ContaminantDB: 3-Carboxy-4-methyl-5-propyl-2-furan-propanoic acid

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (28)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:52:03 UTC

Update Date

2026-08-18 19:02:14 UTC

Accession Number

CHEM003157

Identification

Common Name

3-Carboxy-4-methyl-5-propyl-2-furan-propanoic acid

Class

Small Molecule

Description

3-Carboxy-4-methyl-5-propyl-2-furan-propanoic acid is an endogenous human metabolite with the formula C12H16O5 and an average molecular weight of 240.25 g/mol. At room temperature, this compound exists as a solid. 3-Carboxy-4-methyl-5-propyl-2-furan-propanoic acid belongs to the fatty acids and conjugates, a subclass of fatty acyls within the organic compounds. Biologically, the compound functions as a uremic toxin. It targets the organic anion transporter 3 (SLC22A8). Additionally, it has been recorded as being found in or released from electrical and electronic equipment antennas.

Contaminant Sources

T3DB toxins

Contaminant Type

Ester
Metabolite
Natural Compound
Organic Compound
Uremic Toxin

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 Mass

240.252 g/mol

Monoisotopic Mass

240.100 g/mol

CAS Registry Number

86879-39-2

IUPAC Name

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

Traditional Name

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

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Metabolism and Physiological Effects of 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid (CMPF)	SMP0125515	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	1	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
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-2940000000-c178377899768707f7ef	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-9054000000-b2ed65a9650b6e0bed47	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0002-0900000000-0bcba580e8c7fc7ff28d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-0900000000-d3d2687cc80d9e20e7a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0002-0090000000-20d96334f84cb59f97b4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0090000000-2e3fb6b1387a1189533e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0590000000-b88aab92167a5dbc423e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-0920000000-f8bf7e8f3a2f5e6babdd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9700000000-8cde6db0deca358c0172	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000j-0980000000-46874398810fc7728529	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1910000000-3c88cba9dade4657bc11	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pc0-6900000000-84761c36ced8150db999	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dm-0890000000-464423a298584f86963e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1930000000-39287c920da37a362af1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-6900000000-a12a03c9a4db8d16d281	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-0910000000-057236b313c6ed05bb75	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-0900000000-e17797fad7625863d6b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054k-6900000000-f477479965ef2abe5fc4	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Endogenous, Ingestion, Dermal (contact)

Mechanism of Toxicity

Uremic toxins such as 3-Carboxy-4-methyl-5-propyl-2-furan-propanoic acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (6). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (7).

Metabolism

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Naturally produced by the body (endogenous).

Minimum Risk Level

Not Available

Health Effects

Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.

Symptoms

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Treatment

Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

Concentrations

Not Available

External Links

DrugBank ID

DB07517

HMDB ID

HMDB0061112

FooDB ID

FDB093609

Phenol Explorer ID