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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-07-19 22:32:29 UTC
Update Date2020-11-09 23:21:46 UTC
HMDB IDHMDB0061112
Secondary Accession Numbers
  • HMDB0062776
  • HMDB61112
  • HMDB62776
Metabolite Identification
Common Name3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid
Description3-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
Data?1563866147
Synonyms
ValueSource
CMPFChEBI
3-Carboxy-4-methyl-5-propyl-2-furanpropionateGenerator
3-Carboxy-4-methyl-5-propyl-2-furan-propanoateHMDB
U(3,3)HMDB
CMPFPAHMDB
3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acidHMDB
Propylurofuranic acidHMDB
3-Carboxy-4-methyl-5-propyl-2-furanpropanoateHMDB
2-(2-Carboxyethyl)-4-methyl-4-propylfuran-3-carboxylic acidHMDB
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acidHMDB, ChEBI
Chemical FormulaC12H16O5
Average Molecular Weight240.2524
Monoisotopic Molecular Weight240.099773622
IUPAC Name2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid
Traditional Name2-(2-carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic acid
CAS Registry Number86879-39-2
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 KeyWMCQWXZMVIETAO-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentFuranoid 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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Uremia
  1. Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
  2. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDDB07517
Phenol Explorer Compound IDNot Available
FooDB IDFDB093609
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound123979
PDB IDNot Available
ChEBI ID41254
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References