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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2013-07-19 22:32:29 UTC

Update Date

2020-11-09 23:21:46 UTC

HMDB ID

HMDB0061112

Secondary Accession Numbers

HMDB0062776
HMDB61112
HMDB62776

Metabolite Identification

Common Name

3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid

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>
HMDB0061112

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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 Weight

240.2524

Monoisotopic Molecular Weight

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

86879-39-2

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 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 )

Ontology

Physiological effect

Health effect

Liver damage (PMID: 31434538)
Nerve damage (PMID: 31434538)

Disposition

Biological location

Organ

Placenta (HMDB: HMDB0061112)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20090676)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)
Urine (PMID: 27510537)

Cellular substructure

Membrane (HMDB: HMDB0061112)

Process

Not Available

Role

Biological role

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	155.988	31661259
DarkChem	[M-H]-	153.985	31661259
DeepCCS	[M+H]+	159.801	30932474
DeepCCS	[M-H]-	157.443	30932474
DeepCCS	[M-2H]-	190.628	30932474
DeepCCS	[M+Na]+	166.133	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.9	32859911
AllCCS	[M+NH4]+	159.1	32859911
AllCCS	[M+Na]+	160.1	32859911
AllCCS	[M-H]-	156.5	32859911
AllCCS	[M+Na-2H]-	156.9	32859911
AllCCS	[M+HCOO]-	157.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid	CCCC1=C(C)C(C(O)=O)=C(CCC(O)=O)O1	3011.4	Standard polar	33892256
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid	CCCC1=C(C)C(C(O)=O)=C(CCC(O)=O)O1	1789.3	Standard non polar	33892256
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid	CCCC1=C(C)C(C(O)=O)=C(CCC(O)=O)O1	1964.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid,1TMS,isomer #1	CCCC1=C(C)C(C(=O)O[Si](C)(C)C)=C(CCC(=O)O)O1	2008.3	Semi standard non polar	33892256
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid,1TMS,isomer #2	CCCC1=C(C)C(C(=O)O)=C(CCC(=O)O[Si](C)(C)C)O1	1976.6	Semi standard non polar	33892256
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid,2TMS,isomer #1	CCCC1=C(C)C(C(=O)O[Si](C)(C)C)=C(CCC(=O)O[Si](C)(C)C)O1	1969.3	Semi standard non polar	33892256
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid,1TBDMS,isomer #1	CCCC1=C(C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CCC(=O)O)O1	2237.2	Semi standard non polar	33892256
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid,1TBDMS,isomer #2	CCCC1=C(C)C(C(=O)O)=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O1	2212.4	Semi standard non polar	33892256
3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid,2TBDMS,isomer #1	CCCC1=C(C)C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O1	2440.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-2940000000-c178377899768707f7ef	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00xr-9054000000-b2ed65a9650b6e0bed47	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid LC-ESI-IT , negative-QTOF	splash10-0002-0900000000-0bcba580e8c7fc7ff28d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid Linear Ion Trap , negative-QTOF	splash10-0002-0900000000-d3d2687cc80d9e20e7a5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid Linear Ion Trap , positive-QTOF	splash10-0002-0090000000-20d96334f84cb59f97b4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid Linear Ion Trap , positive-QTOF	splash10-000i-0090000000-2e3fb6b1387a1189533e	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 10V, Positive-QTOF	splash10-006x-0590000000-b88aab92167a5dbc423e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 20V, Positive-QTOF	splash10-002b-0920000000-f8bf7e8f3a2f5e6babdd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 40V, Positive-QTOF	splash10-0udi-9700000000-8cde6db0deca358c0172	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 10V, Negative-QTOF	splash10-000j-0980000000-46874398810fc7728529	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 20V, Negative-QTOF	splash10-0002-1910000000-3c88cba9dade4657bc11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 40V, Negative-QTOF	splash10-0pc0-6900000000-84761c36ced8150db999	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 10V, Positive-QTOF	splash10-00dm-0890000000-464423a298584f86963e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 20V, Positive-QTOF	splash10-004i-1930000000-39287c920da37a362af1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 40V, Positive-QTOF	splash10-00dr-6900000000-a12a03c9a4db8d16d281	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 10V, Negative-QTOF	splash10-002b-0910000000-057236b313c6ed05bb75	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 20V, Negative-QTOF	splash10-0udj-0900000000-e17797fad7625863d6b3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid 40V, Negative-QTOF	splash10-054k-6900000000-f477479965ef2abe5fc4	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	4.6 +/- 4.2 uM	Adult (>18 years old)	Both	Normal	20090676	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24801555	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26264776	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected and Quantified	14.98 +/- 0.83 uM	Adult (>18 years old)	Both	Normal	22626821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	27.3 +/- 35.9 uM	Adult (>18 years old)	Both	End-stage renal failure	20090676	details
Blood	Detected and Quantified	36.63 +/- 20.81 uM	Adult (>18 years old)	Both	uremia	22626821	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Blood	Detected and Quantified	254.167 +/- 68.750 uM	Adult (>18 years old)	Both	Uremia	12675874	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details

Associated Disorders and Diseases

Disease References

Uremia
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 ] 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
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

114500 (Colorectal cancer)

External Links

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

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

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 ]
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. [PubMed:12388676 ]
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 ]
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. [PubMed:11967025 ]
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 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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. 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. Epub 2007 Mar 20. [PubMed:17374880 ]
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 ]
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-furanpropionic acid (HMDB0061112)

MOL for HMDB0061112 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

3D MOL for HMDB0061112 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

3D SDF for HMDB0061112 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

3D-SDF for HMDB0061112 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

PDB for HMDB0061112 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

3D PDB for HMDB0061112 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

SMILES for HMDB0061112 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

INCHI for HMDB0061112 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

Structure for HMDB0061112 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

3D Structure for HMDB0061112 (3-Carboxy-4-methyl-5-propyl-2-furanpropionic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra