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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-08 16:17:30 UTC

Update Date

2022-03-07 03:18:04 UTC

HMDB ID

HMDB0112084

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Methyl-5-pentyl-2-furanpropanoic acid

Description

3-Methyl-5-pentyl-2-furanpropanoic acid is a furan fatty acid (F-acid). F-acids are heterocyclic fatty acids containing a central furan moiety with a carboxylalkyl chain (mostly 7, 9, 11, or 13 carbons) in the 2-position and an alkyl chain (mostly 3 or 5 carbons) in the 5-position. Despite being found in low concentrations in food lipids, they are excellent antixoxidants and radical scavengers. This allows them to play an important role in preventing lipid peroxidation and protecting polyunsaturated fatty acids. They are often incorporated into phospholipids and cholesterol esters of fish and other marine organisms. 3-Methyl-5-pentyl-2-furanpropanoic acid, in particular, can be described by the shorthand notation 3M5. This refers to its 3-carbon carboxyalkyl moiety, the methyl substitution in the 3-position of its furan moiety, and its 5-carbon alkyl moiety. It has been identified in the crayfish hepatopancreas.

Structure

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

HMDB0112084
     RDKit          3D
3-Methyl-5-pentyl-2-furanpropanoic acid
 36 36  0  0  0  0  0  0  0  0999 V2000
    5.5567   -0.0994   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4007    0.8417    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1232    0.0888    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -0.8749   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634   -1.6271   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431   -0.7880   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544    0.5541   -0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.8722   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9328    2.2122   -0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276   -0.3201    0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2690   -0.4349    0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1620   -0.4400   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5827   -0.5550   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8574   -0.6263    1.1569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5710   -0.5819   -1.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184   -1.2542    0.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7865   -0.2513   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3258   -1.0863    0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4652    0.3748    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6196    1.6043    0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2557    1.4040   -0.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -0.4630    1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3483    0.7775    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6998   -0.3496   -1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -1.6331   -0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -2.1527    0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -2.4632   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729    1.2645   -0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3452    2.2832   -1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1871    3.0325   -0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    2.3658    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    0.4436    1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4244   -1.3876    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9300   -1.3242   -1.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0078    0.4448   -1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2317    0.1489   -1.1593 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  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 10 16  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 15 36  1  0
M  END

  Mrv1652309071721522D          

 16 16  0  0  0  0            999 V2000
   -3.5175    1.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2836   -0.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8030    1.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    1.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3741    1.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6596    1.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1810    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5166    1.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1411    0.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481    0.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549    1.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3606    0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371    1.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6726    2.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8220    1.0280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8085    1.3823    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
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  2  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  2  0  0  0  0
 12  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0112084

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC1=CC(C)=C(CCC(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O3/c1-3-4-5-6-11-9-10(2)12(16-11)7-8-13(14)15/h9H,3-8H2,1-2H3,(H,14,15)

> <INCHI_KEY>
QZGKHISFVLMXCZ-UHFFFAOYSA-N

> <FORMULA>
C13H20O3

> <MOLECULAR_WEIGHT>
224.3

> <EXACT_MASS>
224.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.505347616225652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3-methyl-5-pentylfuran-2-yl)propanoic acid

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.529113056666666

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.650726849555827

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7367550962906346

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
63.0294

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3-methyl-5-pentylfuran-2-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0112084
     RDKit          3D
3-Methyl-5-pentyl-2-furanpropanoic acid
 36 36  0  0  0  0  0  0  0  0999 V2000
    5.5567   -0.0994   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4007    0.8417    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1232    0.0888    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -0.8749   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634   -1.6271   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431   -0.7880   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544    0.5541   -0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.8722   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9328    2.2122   -0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276   -0.3201    0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2690   -0.4349    0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1620   -0.4400   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5827   -0.5550   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8574   -0.6263    1.1569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5710   -0.5819   -1.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184   -1.2542    0.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7865   -0.2513   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3258   -1.0863    0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4652    0.3748    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6196    1.6043    0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2557    1.4040   -0.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -0.4630    1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3483    0.7775    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6998   -0.3496   -1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -1.6331   -0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -2.1527    0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -2.4632   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729    1.2645   -0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3452    2.2832   -1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1871    3.0325   -0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    2.3658    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    0.4436    1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4244   -1.3876    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9300   -1.3242   -1.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0078    0.4448   -1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2317    0.1489   -1.1593 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  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 10 16  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 15 36  1  0
M  END

HEADER    PROTEIN                                 07-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-17         0                                  
HETATM    1  C   UNK     0      -6.566   2.724   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.396  -1.305   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.232   1.954   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.899   2.724   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.565   1.954   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.231   2.724   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.071   1.597   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.698   3.004   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.263   0.422   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.770   0.102   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.102   1.954   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.540   1.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.229   3.165   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.856   4.572   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       7.134   1.919   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.509   2.580   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   10                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5   11                                                       
CONECT    7    8   12                                                       
CONECT    8    7   13                                                       
CONECT    9   10   11                                                       
CONECT   10    2    9   12                                                  
CONECT   11    6    9   16                                                  
CONECT   12    7   10   16                                                  
CONECT   13    8   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0112084
HETATM    1  C1  UNL     1       5.557  -0.099  -0.034  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.401   0.842   0.187  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.123   0.089   0.573  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.710  -0.875  -0.484  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.463  -1.627  -0.188  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.243  -0.788  -0.070  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.054   0.554  -0.322  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.270   0.872  -0.058  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.933   2.212  -0.190  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.828  -0.320   0.348  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.269  -0.435   0.737  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.162  -0.440  -0.474  1.00  0.00           C  
HETATM   13  C13 UNL     1      -5.583  -0.555  -0.067  1.00  0.00           C  
HETATM   14  O1  UNL     1      -5.857  -0.626   1.157  1.00  0.00           O  
HETATM   15  O2  UNL     1      -6.571  -0.582  -1.023  1.00  0.00           O  
HETATM   16  O3  UNL     1      -0.918  -1.254   0.326  1.00  0.00           O  
HETATM   17  H1  UNL     1       5.786  -0.251  -1.118  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.326  -1.086   0.378  1.00  0.00           H  
HETATM   19  H3  UNL     1       6.465   0.375   0.392  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.620   1.604   0.966  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.256   1.404  -0.762  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.442  -0.463   1.521  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.348   0.777   0.934  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.700  -0.350  -1.461  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.529  -1.633  -0.579  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.638  -2.153   0.799  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.275  -2.463  -0.905  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.773   1.264  -0.674  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.345   2.283  -1.210  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.187   3.032  -0.051  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.692   2.366   0.606  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.501   0.444   1.338  1.00  0.00           H  
HETATM   33  H17 UNL     1      -3.424  -1.388   1.277  1.00  0.00           H  
HETATM   34  H18 UNL     1      -3.930  -1.324  -1.133  1.00  0.00           H  
HETATM   35  H19 UNL     1      -4.008   0.445  -1.123  1.00  0.00           H  
HETATM   36  H20 UNL     1      -7.232   0.149  -1.159  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7    7   16
CONECT    7    8   28
CONECT    8    9   10   10
CONECT    9   29   30   31
CONECT   10   11   16
CONECT   11   12   32   33
CONECT   12   13   34   35
CONECT   13   14   14   15
CONECT   15   36
END

HMDB0112084
     RDKit          3D
3-Methyl-5-pentyl-2-furanpropanoic acid
 36 36  0  0  0  0  0  0  0  0999 V2000
    5.5567   -0.0994   -0.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4007    0.8417    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1232    0.0888    0.5728 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7097   -0.8749   -0.4843 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4634   -1.6271   -0.1884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2431   -0.7880   -0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0544    0.5541   -0.3218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.8722   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9328    2.2122   -0.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8276   -0.3201    0.3478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2690   -0.4349    0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1620   -0.4400   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5827   -0.5550   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8574   -0.6263    1.1569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5710   -0.5819   -1.0234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184   -1.2542    0.3264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7865   -0.2513   -1.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3258   -1.0863    0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4652    0.3748    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6196    1.6043    0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2557    1.4040   -0.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417   -0.4630    1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3483    0.7775    0.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6998   -0.3496   -1.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -1.6331   -0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -2.1527    0.7990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2751   -2.4632   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729    1.2645   -0.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3452    2.2832   -1.2097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1871    3.0325   -0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6921    2.3658    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5007    0.4436    1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4244   -1.3876    1.2773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9300   -1.3242   -1.1326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0078    0.4448   -1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2317    0.1489   -1.1593 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  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 10 16  1  0
 16  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 15 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Methyl-5-pentyl-2-furanpropanoate	Generator
3-(3-Methyl-5-pentylfuran-2-yl)propanoate	HMDB
3M5	HMDB
MonoMe(3,5)	HMDB
3-(3-Methyl-5-pentyl-2-furyl)propanoic acid	HMDB
4,7-Epoxy-5-methyl-4,6-dodecadienoic acid	HMDB
4,7-Epoxy-5-methyldodeca-4,6-dienoic acid	HMDB
3-(3-Methyl-5-pentylfuran-2-yl)propanoic acid	HMDB
3-methyl-5-pentyl-2-furanpropanoic acid	SMPDB

Chemical Formula

C₁₃H₂₀O₃

Average Molecular Weight

224.3

Monoisotopic Molecular Weight

224.141244504

IUPAC Name

3-(3-methyl-5-pentylfuran-2-yl)propanoic acid

Traditional Name

3-(3-methyl-5-pentylfuran-2-yl)propanoic acid

CAS Registry Number

69662-69-7

SMILES

CCCCCC1=CC(C)=C(CCC(O)=O)O1

InChI Identifier

InChI=1S/C13H20O3/c1-3-4-5-6-11-9-10(2)12(16-11)7-8-13(14)15/h9H,3-8H2,1-2H3,(H,14,15)

InChI Key

QZGKHISFVLMXCZ-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
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0112084)

Process

Not Available

Role

Not Available

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
logP	3.71	ALOGPS
logP	3.53	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	63.03 m³·mol⁻¹	ChemAxon
Polarizability	26.51 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]+	154.716	31661259
DarkChem	[M-H]-	151.767	31661259
DeepCCS	[M+H]+	161.834	30932474
DeepCCS	[M-H]-	158.113	30932474
DeepCCS	[M-2H]-	194.441	30932474
DeepCCS	[M+Na]+	170.649	30932474
AllCCS	[M+H]+	155.4	32859911
AllCCS	[M+H-H2O]+	151.6	32859911
AllCCS	[M+NH4]+	159.0	32859911
AllCCS	[M+Na]+	160.0	32859911
AllCCS	[M-H]-	158.6	32859911
AllCCS	[M+Na-2H]-	159.4	32859911
AllCCS	[M+HCOO]-	160.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-5-pentyl-2-furanpropanoic acid	CCCCCC1=CC(C)=C(CCC(O)=O)O1	2773.4	Standard polar	33892256
3-Methyl-5-pentyl-2-furanpropanoic acid	CCCCCC1=CC(C)=C(CCC(O)=O)O1	1671.1	Standard non polar	33892256
3-Methyl-5-pentyl-2-furanpropanoic acid	CCCCCC1=CC(C)=C(CCC(O)=O)O1	1722.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-5-pentyl-2-furanpropanoic acid,1TMS,isomer #1	CCCCCC1=CC(C)=C(CCC(=O)O[Si](C)(C)C)O1	1810.1	Semi standard non polar	33892256
3-Methyl-5-pentyl-2-furanpropanoic acid,1TBDMS,isomer #1	CCCCCC1=CC(C)=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O1	2021.1	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-Methyl-5-pentyl-2-furanpropanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00bl-9330000000-64bf6f09286aa3f6d391	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 10V, Positive-QTOF	splash10-0a6r-0290000000-d3eb99f999f792125a54	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 20V, Positive-QTOF	splash10-0a6r-5930000000-bde575cdbc9c8330ea6a	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 40V, Positive-QTOF	splash10-0a4i-9200000000-d94403e750b1ffa9a8f4	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 10V, Negative-QTOF	splash10-00di-0190000000-7edb5f68a69199d594b1	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 20V, Negative-QTOF	splash10-0ab9-3790000000-abd2396f07218ab31127	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 40V, Negative-QTOF	splash10-0abc-7900000000-5da04a5db670f1f6386d	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 10V, Positive-QTOF	splash10-004i-0190000000-b691fadbc0bf1f571d7f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 20V, Positive-QTOF	splash10-004i-3950000000-b81b4a5735359c281bc4	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 40V, Positive-QTOF	splash10-052f-9300000000-c7f474e7697e69cf26ed	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 10V, Negative-QTOF	splash10-00di-0090000000-cc77f15b3fff803d20c1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 20V, Negative-QTOF	splash10-0ab9-9540000000-88caff7418ffcdbf9751	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpropanoic acid 40V, Negative-QTOF	splash10-0596-7900000000-16d3d28ebf81c8a8dc2c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

74849740

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85564647

PDB ID

Not Available

ChEBI ID

Not Available

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

Ishii K, Okajima H, Koyamatsu T, Okada Y, Watanabe H: The composition of furan fatty acids in the crayfish. Lipids. 1988 Jul;23(7):694-700. doi: 10.1007/BF02535671. [PubMed:27520122 ]
Vetter W, Wendlinger C (2013). Furan fatty acids – valuable minor fatty acids in food. Lipid Technology.

Showing metabocard for 3-Methyl-5-pentyl-2-furanpropanoic acid (HMDB0112084)

MOL for HMDB0112084 (3-Methyl-5-pentyl-2-furanpropanoic acid)

3D MOL for HMDB0112084 (3-Methyl-5-pentyl-2-furanpropanoic acid)

3D SDF for HMDB0112084 (3-Methyl-5-pentyl-2-furanpropanoic acid)

3D-SDF for HMDB0112084 (3-Methyl-5-pentyl-2-furanpropanoic acid)

PDB for HMDB0112084 (3-Methyl-5-pentyl-2-furanpropanoic acid)

3D PDB for HMDB0112084 (3-Methyl-5-pentyl-2-furanpropanoic acid)

SMILES for HMDB0112084 (3-Methyl-5-pentyl-2-furanpropanoic acid)

INCHI for HMDB0112084 (3-Methyl-5-pentyl-2-furanpropanoic acid)

Structure for HMDB0112084 (3-Methyl-5-pentyl-2-furanpropanoic acid)

3D Structure for HMDB0112084 (3-Methyl-5-pentyl-2-furanpropanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra