MiMeDB: Showing metabocard for 3-Carboxy-4-methyl-5-propyl-2-furanpropanoate (MMDBc0000703)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:53:06 UTC

Update Date

2022-08-31 06:11:16 UTC

MiMeDB ID

MMDBc0000703

Metabolite Identification

Common Name

3-Carboxy-4-methyl-5-propyl-2-furanpropanoate

Description

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

Not Available

Chemical Formula

C₁₂H₁₆O₅

Average Molecular Weight

240.2524

Monoisotopic Molecular Weight

240.099773622

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference
Uremia	Increased	This associated disease is originally imported from HMDB metabolite HMDB0061112 concentration id 162046	Association	Human Blood		12675874	details
Uremia	Increased	This associated disease is originally imported from HMDB metabolite HMDB0061112 concentration id 90418	Association	Human Blood		22626821	details

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Firmicutes	1		Indirect association between microbiota composition and metabolites measured in host biospecimen
	Bacteroidetes	1		Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Age	Sex	Health Condition	Data Source	Reference
Human	Detected and Quantified	254.167	68.750	Adult (>18 years old)	Both	Uremia	HMDB	12675874	details
Human	Detected and Quantified	36.63	20.81	Adult (>18 years old)	Both	uremia	HMDB	22626821	details
Human	Detected and Quantified	14.98	0.83	Adult (>18 years old)	Both	Normal	HMDB	22626821	details
Human	Detected and Quantified	4.6	4.2	Adult (>18 years old)	Both	Normal	HMDB	20090676	details
Human Placenta	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597	details
Human Blood	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	24740205	details
Human Blood	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	24740205	details
Human Blood	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	24740205	details
Human Blood	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	24801555	details
Human Blood	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	26264776	details
Human Blood	Detected but not Quantified			Adult (>18 years old)	Female	Normal	HMDB	27355821	details
Human Blood	Detected but not Quantified			Adult (>18 years old)	Female	Normal	HMDB	27355821	details
Human Blood	Detected but not Quantified			Adult (>18 years old)	Female	Normal	HMDB	27355821	details
Human Blood	Detected but not Quantified			Adult (>18 years old)	Female	Normal	HMDB	27355821	details
Human Urine	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	32966057	details
Human Blood	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	32966057	details

External Links

Not Available

References

Synthesis Reference

Not Available

General References

Niwa T: Organic acids and the uremic syndrome: protein metabolite hypothesis in the progression of chronic renal failure. Semin Nephrol. 1996 May;16(3):167-82. [PubMed:8734460 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Deguchi T, Ohtsuki S, Otagiri M, Takanaga H, Asaba H, Mori S, Terasaki T: Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney. Kidney Int. 2002 May;61(5):1760-8. doi: 10.1046/j.1523-1755.2002.00318.x. [PubMed:11967025 ]
Tsutsumi Y, Deguchi T, Takano M, Takadate A, Lindup WE, Otagiri M: Renal disposition of a furan dicarboxylic acid and other uremic toxins in the rat. J Pharmacol Exp Ther. 2002 Nov;303(2):880-7. doi: 10.1124/jpet.303.2.880. [PubMed:12388676 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Niwa T: Recent progress in the analysis of uremic toxins by mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Sep 1;877(25):2600-6. doi: 10.1016/j.jchromb.2008.11.032. Epub 2008 Nov 27. [PubMed:19083276 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 3-Carboxy-4-methyl-5-propyl-2-furanpropanoate (MMDBc0000703)

MOL for #<Metabolite:0x000055b76bdd7200>

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SMILES for #<Metabolite:0x000055b76bdd7200>

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Structure for #<Metabolite:0x000055b76bdd7200>

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