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

2024-04-30 19:33:34 UTC

Metabolite 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 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0061112
     RDKit          3D
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    2.7483    1.9512    0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484    1.1112   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873    0.7624   -1.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0521    0.0076   -0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    0.5801   -0.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884   -0.2623   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944    0.0818    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    1.5568    0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0882    1.8325    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0072    1.5775   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4244    2.3761    1.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -1.5063   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0981   -2.7175    0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3266   -2.6529    0.7150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -3.9616    0.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811   -1.3288   -0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322   -2.3312   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6595    1.8859    0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1294    2.9902    0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1715    1.4970    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9743    1.7657   -0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8728    0.2529    0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6891    0.1600   -2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8684    1.6866   -1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0727   -0.5115   -0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692   -0.1437    1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9818    2.1945    0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5779    1.7835   -1.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1590    1.8957    2.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429   -4.5773   -0.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230   -2.2209    0.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -2.3859   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293   -3.3492   -0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 16  4  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
M  END


  Mrv1652310151921552D          

 17 17  0  0  0  0            999 V2000
    1.2822    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -2.9975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -2.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
 17  8  1  0  0  0  0
 17  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000703

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C12H16O5

> <MOLECULAR_WEIGHT>
240.2524

> <EXACT_MASS>
240.099773622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.26012299065896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
2.2975586346666668

> <ALOGPS_LOGS>
-3.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.784928733133732

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8672044770544063

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9255026501474064

> <JCHEM_POLAR_SURFACE_AREA>
87.74

> <JCHEM_REFRACTIVITY>
61.083600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061112
     RDKit          3D
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    2.7483    1.9512    0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484    1.1112   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873    0.7624   -1.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0521    0.0076   -0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    0.5801   -0.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884   -0.2623   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944    0.0818    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    1.5568    0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0882    1.8325    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0072    1.5775   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4244    2.3761    1.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -1.5063   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0981   -2.7175    0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3266   -2.6529    0.7150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -3.9616    0.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811   -1.3288   -0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322   -2.3312   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6595    1.8859    0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1294    2.9902    0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1715    1.4970    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9743    1.7657   -0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8728    0.2529    0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6891    0.1600   -2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8684    1.6866   -1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0727   -0.5115   -0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692   -0.1437    1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9818    2.1945    0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5779    1.7835   -1.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1590    1.8957    2.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429   -4.5773   -0.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230   -2.2209    0.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -2.3859   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293   -3.3492   -0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 16  4  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
M  END

HEADER    PROTEIN                                 15-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-OCT-19         0                                  
HETATM    1  C   UNK     0       2.393   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.894  -4.188   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.268  -5.595   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.426  -4.027   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.109  -2.943   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.267  -1.375   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    7                                                            
CONECT    3    1    4                                                       
CONECT    4    3    8                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    2    8   11                                                  
CONECT    8    4    7   17                                                  
CONECT    9    5   11   17                                                  
CONECT   10    6   13   14                                                  
CONECT   11    7    9   12                                                  
CONECT   12   11   15   16                                                  
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15   12                                                            
CONECT   16   12                                                            
CONECT   17    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0061112
HETATM    1  C1  UNL     1       2.748   1.951   0.897  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.248   1.111  -0.259  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.187   0.762  -1.233  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.052   0.008  -0.765  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.111   0.580  -0.550  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.988  -0.262  -0.137  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.394   0.082   0.192  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.662   1.557   0.010  1.00  0.00           C  
HETATM    9  C8  UNL     1      -4.088   1.833   0.352  1.00  0.00           C  
HETATM   10  O2  UNL     1      -5.007   1.577  -0.466  1.00  0.00           O  
HETATM   11  O3  UNL     1      -4.424   2.376   1.583  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.424  -1.506  -0.050  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.098  -2.718   0.380  1.00  0.00           C  
HETATM   14  O4  UNL     1      -2.327  -2.653   0.715  1.00  0.00           O  
HETATM   15  O5  UNL     1      -0.546  -3.962   0.470  1.00  0.00           O  
HETATM   16  C11 UNL     1       0.881  -1.329  -0.453  1.00  0.00           C  
HETATM   17  C12 UNL     1       1.932  -2.331  -0.551  1.00  0.00           C  
HETATM   18  H1  UNL     1       1.659   1.886   0.981  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.129   2.990   0.873  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.172   1.497   1.840  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.974   1.766  -0.817  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.873   0.253   0.067  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.689   0.160  -2.050  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.868   1.687  -1.745  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.073  -0.512  -0.453  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.569  -0.144   1.268  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.982   2.195   0.570  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.578   1.783  -1.093  1.00  0.00           H  
HETATM   29  H12 UNL     1      -4.159   1.896   2.449  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.643  -4.577  -0.347  1.00  0.00           H  
HETATM   31  H14 UNL     1       2.723  -2.221   0.249  1.00  0.00           H  
HETATM   32  H15 UNL     1       2.407  -2.386  -1.560  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.529  -3.349  -0.366  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5   16   16
CONECT    5    6
CONECT    6    7   12   12
CONECT    7    8   25   26
CONECT    8    9   27   28
CONECT    9   10   10   11
CONECT   11   29
CONECT   12   13   16
CONECT   13   14   14   15
CONECT   15   30
CONECT   16   17
CONECT   17   31   32   33
END

HMDB0061112
     RDKit          3D
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid
 33 33  0  0  0  0  0  0  0  0999 V2000
    2.7483    1.9512    0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2484    1.1112   -0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873    0.7624   -1.2330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0521    0.0076   -0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1110    0.5801   -0.5502 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884   -0.2623   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944    0.0818    0.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    1.5568    0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0882    1.8325    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0072    1.5775   -0.4662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4244    2.3761    1.5827 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236   -1.5063   -0.0502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0981   -2.7175    0.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3266   -2.6529    0.7150 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -3.9616    0.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811   -1.3288   -0.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9322   -2.3312   -0.5509 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6595    1.8859    0.9811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1294    2.9902    0.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1715    1.4970    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9743    1.7657   -0.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8728    0.2529    0.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6891    0.1600   -2.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8684    1.6866   -1.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0727   -0.5115   -0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5692   -0.1437    1.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9818    2.1945    0.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5779    1.7835   -1.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1590    1.8957    2.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429   -4.5773   -0.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7230   -2.2209    0.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -2.3859   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293   -3.3492   -0.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  6 12  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 12 16  1  0
 16 17  1  0
 16  4  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 15 30  1  0
 17 31  1  0
 17 32  1  0
 17 33  1  0
M  END

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

Molecular Formula

C₁₂H₁₆O₅

Average Mass

240.2524

Monoisotopic Mass

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

Not Available

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

Not Available

Physical Properties

State

Expected Solid

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-2940000000-c178377899768707f7ef	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-9054000000-b2ed65a9650b6e0bed47	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0002-0900000000-0bcba580e8c7fc7ff28d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0002-0900000000-d3d2687cc80d9e20e7a5	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0002-0090000000-20d96334f84cb59f97b4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0090000000-2e3fb6b1387a1189533e	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0590000000-b88aab92167a5dbc423e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-0920000000-f8bf7e8f3a2f5e6babdd	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9700000000-8cde6db0deca358c0172	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000j-0980000000-46874398810fc7728529	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1910000000-3c88cba9dade4657bc11	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pc0-6900000000-84761c36ced8150db999	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dm-0890000000-464423a298584f86963e	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1930000000-39287c920da37a362af1	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-6900000000-a12a03c9a4db8d16d281	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-0910000000-057236b313c6ed05bb75	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-0900000000-e17797fad7625863d6b3	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054k-6900000000-f477479965ef2abe5fc4	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

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

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Uremia	Increased	Association	Human Blood	HMDB	12675874
Uremia	Increased	Association	Human Blood	HMDB	22626821

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

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

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:0x00007fd12c36aab0>

3D MOL for #<Metabolite:0x00007fd12c36aab0>

3D SDF for #<Metabolite:0x00007fd12c36aab0>

3D-SDF for #<Metabolite:0x00007fd12c36aab0>

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3D Structure for #<Metabolite:0x00007fd12c36aab0>