3-Carboxy-4-Methyl-5-Propyl-2-Furanpropanoic Acid
Basic information
- CAS
86879-39-2- Standard SMILES
CCCc1oc(CCC(=O)O)c(C(=O)O)c1C- InChIKey
WMCQWXZMVIETAO-UHFFFAOYSA-N- Molecular formula
- C12H16O5
- Average molar mass
- 240.25 g/mol
- Monoisotopic mass
- 240.09977361
Overview
2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid is a furoic acid that is furan-3-carboxylic acid substituted by a methyl group at position 4, a propyl group at position 5 and a 2-carboxyethyl group at position 2. It is a potent uremic toxin that has been found to accumulate in human serum of patients with chronic kidney diseases. It has a role as a uremic toxin and a human metabolite. It is a dicarboxylic acid and a furoic acid. It is a conjugate acid of a 3-carboxy-4-methyl-5-propyl-2-furanpropionate(2-) and a 3-carboxy-4-methyl-5-propyl-2-furanpropanoate.
Names & identifiers
- Preferred name
- 3-Carboxy-4-Methyl-5-Propyl-2-Furanpropanoic Acid
- IUPAC
- 2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid
- English name
- CMPF
- Molecular formula
- C12H16O5
- Molecular weight
- 240.25
Names & synonyms
86879-39-23-carboxy-4-methyl-5-propyl-2-furanpropionic acidCmpfpa3-carboxy-4-methyl-5-propyl-2-furanpropanoic acidDTXSID902359402-Furanpropanoic acid, 3-carboxy-4-methyl-5-propyl-, (2S-(2alpha,3beta,4aalpha,12balpha))-CMPF cpdRefChem:453512DTXCID201584313-carboxy-4-methyl-5-propyl-2-furan-propionic acidCMPF2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid
Show more names
Furanic acidD3-CMPF(Major)CMPF ExclusivePropylfuranoic acid3-Carboxy-4-methyl-5-propylfuran 2-propanoic acid2-Furanpropanoic acid, 3-carboxy-4-methyl-5-propyl-CMPF, 3-carboxy-4-methyl-5-propyl-2-furanpropionic acid
3-CARBOXY-4-METHYL-5-PROPYL-2-FURANPROPIONICJTU41879GFAKOS0302550993-Carboxy-4-methyl-5-propyl-2-furanpropionate2-FURANPROPIONIC ACID, 3-CARBOXY-4-METHYL-5-PROPYL-3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid, analytical standardPROPYLUROFURANIC ACID3-Carboxy-4-methyl-5-propyl-2-furanpropionic Acid; 3-Carboxy-4-methyl-5-propyl-2-furanpropanoic Acid; Propylurofuranic Acid; 2-(2-Carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic Acid;
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 87.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 289
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Heterocyclic fatty acids [FA0115]
Physicochemical properties
- Melting point
- 174 °C · >174°C (Subl.)
- Boiling point
- 404 · 404.0±45.0 °C(Predicted)
- Density
- 1.236 · 1.236±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Very Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol
- pka
- 4.38 · 4.38±0.10(Predicted)
- form
- Solid
- color
- White to Pale Beige
- Major Application
- clinical testing
- 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)
- InChIKey
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary
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) (A7868). 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 (A7869).
Signs and 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.
Chemistry & industry
Pharmacology
Metabolism/MetabolitesUremic 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.
Tissue LocationsPlacenta
Cellular LocationsMembrane
Uses & manufacturing
UsesNaturally produced by the body (endogenous).
Applications
UsesCMPF is a drug-binding inhibitor which is also a constituent of urine. CMPF can inhibit specific T4 binding in serum by increasing the free concentration of direct competitors.
General Description3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid (CMPF), a major metabolite of furan fatty acids, is a uremic toxin (UT), excreted into the urine via organic,anion transporters under physiological conditions. It is mostly reported to be accumulated in chronic kidney disease (CKD) patients. Monitoring of CMPF may be important to predict organic anion transporting polypeptide (OATP)1B activity in CKD patients as studies have implicated a decreased trend in (OATP)1B activity in patients with this uremic toxin. It is also found to be in increased concentrations, for patients who progress from prediabetes to type 2 diabetes, patients with renal failure, polyunsaturated fatty acids with high-temperature cooking and subjects who consume fish or fish oil.
Additional notes
DefinitionChEBI: A furoic acid that is furan-3-carboxylic acid substituted by a methyl group at position 4, a propyl group at position 5 and a 2-carboxyethyl group at position 2. It is a potent uremic toxin that has been found to accumulate in human serum of patients with hronic kidney diseases.
Related reactions
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Compound notes
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