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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-08 16:17:45 UTC

Update Date

2022-03-07 03:18:04 UTC

HMDB ID

HMDB0112086

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Methyl-5-pentyl-2-furanpentanoic acid

Description

3-Methyl-5-pentyl-2-furanpentanoic 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-furanpentanoic acid, in particular, can be described by the shorthand notation 5M5. This refers to its 5-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 fish oil.

Structure

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

HMDB0112086
     RDKit          3D
3-Methyl-5-pentyl-2-furanpentanoic acid
 42 42  0  0  0  0  0  0  0  0999 V2000
    6.8456    0.1369   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3702    0.4702   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6944   -0.0850    0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2146    0.1806    0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979   -0.4280   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0466   -0.1077   -0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121    1.0016   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9564    0.9334   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9609    1.9698   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0693   -0.2324    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2529   -0.8613    1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -1.6815    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7655   -1.0032   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8197   -0.0140   -0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9590   -0.6287    0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9726   -1.8584    0.2953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0072    0.1332    0.5756 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1350   -0.8138    0.5279 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0275   -0.8310    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3894    0.9391    0.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3269    0.1303   -1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835    1.5545   -0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.0612   -1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1441    0.4318    1.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8980   -1.1530    1.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8217   -0.2216    1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615    1.2775    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8825   -0.0689   -1.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457   -1.5352   -0.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8442    1.8180   -1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340    1.7333   -1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5645    2.2549    0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    2.9404   -0.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8941   -0.0671    1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9519   -1.5401    1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867   -2.2762    0.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4097   -2.5076   -0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2986   -1.8118   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9753   -0.5671   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4204    0.8331   -0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2480    0.4781   -1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0812    1.1380    0.4584 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  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 10 18  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 17 42  1  0
M  END


  Mrv1652309071721522D          

 18 18  0  0  0  0            999 V2000
   11.6827   -1.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0671    2.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3472   -1.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5267   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1911   -0.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7130    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9985    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3707   -0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4274    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2840    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4476    1.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8956    1.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0351    0.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1419    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8551    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5695    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2281    0.6085    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
  7  6  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 12  2  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 14 12  2  0  0  0  0
 15 10  1  0  0  0  0
 16 15  2  0  0  0  0
 17 15  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0112086

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O3/c1-3-4-5-8-13-11-12(2)14(18-13)9-6-7-10-15(16)17/h11H,3-10H2,1-2H3,(H,16,17)

> <INCHI_KEY>
OVQQXXHYNCJQNP-UHFFFAOYSA-N

> <FORMULA>
C15H24O3

> <MOLECULAR_WEIGHT>
252.354

> <EXACT_MASS>
252.172544633

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.657174332837407

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.48

> <JCHEM_LOGP>
4.418250386666667

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.712749401028006

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6701751326925938

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
72.2314

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0112086
     RDKit          3D
3-Methyl-5-pentyl-2-furanpentanoic acid
 42 42  0  0  0  0  0  0  0  0999 V2000
    6.8456    0.1369   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3702    0.4702   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6944   -0.0850    0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2146    0.1806    0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979   -0.4280   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0466   -0.1077   -0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121    1.0016   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9564    0.9334   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9609    1.9698   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0693   -0.2324    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2529   -0.8613    1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -1.6815    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7655   -1.0032   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8197   -0.0140   -0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9590   -0.6287    0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9726   -1.8584    0.2953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0072    0.1332    0.5756 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1350   -0.8138    0.5279 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0275   -0.8310    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3894    0.9391    0.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3269    0.1303   -1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835    1.5545   -0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.0612   -1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1441    0.4318    1.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8980   -1.1530    1.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8217   -0.2216    1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615    1.2775    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8825   -0.0689   -1.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457   -1.5352   -0.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8442    1.8180   -1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340    1.7333   -1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5645    2.2549    0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    2.9404   -0.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8941   -0.0671    1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9519   -1.5401    1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867   -2.2762    0.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4097   -2.5076   -0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2986   -1.8118   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9753   -0.5671   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4204    0.8331   -0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2480    0.4781   -1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0812    1.1380    0.4584 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  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 10 18  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 17 42  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      21.808  -3.727   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.925   4.800   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.181  -2.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.650  -2.159   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.023  -0.752   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.531   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.197   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.492  -0.591   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.865   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.863   2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.636   2.149   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.605   3.294   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.866   0.816   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.198   2.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.530   3.437   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.196   2.667   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.530   4.977   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      15.359   1.136   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   12                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    8                                                       
CONECT    6    7    9                                                       
CONECT    7    6   10                                                       
CONECT    8    5   13                                                       
CONECT    9    6   14                                                       
CONECT   10    7   15                                                       
CONECT   11   12   13                                                       
CONECT   12    2   11   14                                                  
CONECT   13    8   11   18                                                  
CONECT   14    9   12   18                                                  
CONECT   15   10   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0112086
HETATM    1  C1  UNL     1       6.846   0.137  -0.172  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.370   0.470  -0.268  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.694  -0.085   0.958  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.215   0.181   0.984  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.498  -0.428  -0.201  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.047  -0.108  -0.075  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.412   1.002  -0.580  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.956   0.933  -0.247  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.961   1.970  -0.589  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.069  -0.232   0.449  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.253  -0.861   1.059  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.080  -1.682   0.135  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.765  -1.003  -0.989  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.820  -0.014  -0.619  1.00  0.00           C  
HETATM   15  C15 UNL     1      -5.959  -0.629   0.106  1.00  0.00           C  
HETATM   16  O1  UNL     1      -5.973  -1.858   0.295  1.00  0.00           O  
HETATM   17  O2  UNL     1      -7.007   0.133   0.576  1.00  0.00           O  
HETATM   18  O3  UNL     1       0.135  -0.814   0.528  1.00  0.00           O  
HETATM   19  H1  UNL     1       7.028  -0.831   0.342  1.00  0.00           H  
HETATM   20  H2  UNL     1       7.389   0.939   0.402  1.00  0.00           H  
HETATM   21  H3  UNL     1       7.327   0.130  -1.174  1.00  0.00           H  
HETATM   22  H4  UNL     1       5.284   1.554  -0.361  1.00  0.00           H  
HETATM   23  H5  UNL     1       4.995  -0.061  -1.191  1.00  0.00           H  
HETATM   24  H6  UNL     1       5.144   0.432   1.833  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.898  -1.153   1.044  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.822  -0.222   1.938  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.061   1.278   1.015  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.882  -0.069  -1.160  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.646  -1.535  -0.114  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.844   1.818  -1.145  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.634   1.733  -1.400  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.565   2.255   0.322  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.429   2.940  -0.832  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.894  -0.067   1.531  1.00  0.00           H  
HETATM   35  H17 UNL     1      -1.952  -1.540   1.903  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.787  -2.276   0.773  1.00  0.00           H  
HETATM   37  H19 UNL     1      -2.410  -2.508  -0.288  1.00  0.00           H  
HETATM   38  H20 UNL     1      -4.299  -1.812  -1.592  1.00  0.00           H  
HETATM   39  H21 UNL     1      -2.975  -0.567  -1.644  1.00  0.00           H  
HETATM   40  H22 UNL     1      -4.420   0.833  -0.026  1.00  0.00           H  
HETATM   41  H23 UNL     1      -5.248   0.478  -1.541  1.00  0.00           H  
HETATM   42  H24 UNL     1      -7.081   1.138   0.458  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7    7   18
CONECT    7    8   30
CONECT    8    9   10   10
CONECT    9   31   32   33
CONECT   10   11   18
CONECT   11   12   34   35
CONECT   12   13   36   37
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16   16   17
CONECT   17   42
END

HMDB0112086
     RDKit          3D
3-Methyl-5-pentyl-2-furanpentanoic acid
 42 42  0  0  0  0  0  0  0  0999 V2000
    6.8456    0.1369   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3702    0.4702   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6944   -0.0850    0.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2146    0.1806    0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979   -0.4280   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0466   -0.1077   -0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4121    1.0016   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9564    0.9334   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9609    1.9698   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0693   -0.2324    0.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2529   -0.8613    1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0797   -1.6815    0.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7655   -1.0032   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8197   -0.0140   -0.6186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9590   -0.6287    0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9726   -1.8584    0.2953 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0072    0.1332    0.5756 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1350   -0.8138    0.5279 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0275   -0.8310    0.3416 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3894    0.9391    0.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3269    0.1303   -1.1742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2835    1.5545   -0.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9954   -0.0612   -1.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1441    0.4318    1.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8980   -1.1530    1.0442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8217   -0.2216    1.9381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615    1.2775    1.0149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8825   -0.0689   -1.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457   -1.5352   -0.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8442    1.8180   -1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6340    1.7333   -1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5645    2.2549    0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4294    2.9404   -0.8315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8941   -0.0671    1.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9519   -1.5401    1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7867   -2.2762    0.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4097   -2.5076   -0.2885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2986   -1.8118   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9753   -0.5671   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4204    0.8331   -0.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2480    0.4781   -1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0812    1.1380    0.4584 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  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 10 18  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 17 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-(3-Methyl-5-pentylfuran-2-yl)-pentanoate	Generator
5M5	SMPDB, HMDB
MonoMe(5,5)	SMPDB, HMDB
5-(3-methyl-5-pentyl-2-furyl)pentanoic acid	SMPDB, HMDB
3-methyl-5-pentyl-2-furanpentanoic acid	SMPDB
6,9-epoxy-7-methyl-6,8-tetradecadienoic acid	SMPDB, HMDB
6,9-epoxy-7-methyltetradeca-6,8-dienoic acid	SMPDB, HMDB
5-(3-methyl-5-pentylfuran-2-yl)pentanoic acid	SMPDB, HMDB
3-Methyl-5-pentylfuran-2-pentanoate	Generator, HMDB
3-Methyl-5-pentyl-2-furanpentanoate	Generator

Chemical Formula

C₁₅H₂₄O₃

Average Molecular Weight

252.354

Monoisotopic Molecular Weight

252.172544633

IUPAC Name

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

Traditional Name

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

CAS Registry Number

157686-84-5

SMILES

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

InChI Identifier

InChI=1S/C15H24O3/c1-3-4-5-8-13-11-12(2)14(18-13)9-6-7-10-15(16)17/h11H,3-10H2,1-2H3,(H,16,17)

InChI Key

OVQQXXHYNCJQNP-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
Medium-chain 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

Not Available

Not Available

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	4.48	ALOGPS
logP	4.42	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.71	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	9	ChemAxon
Refractivity	72.23 m³·mol⁻¹	ChemAxon
Polarizability	30.66 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]+	162.369	31661259
DarkChem	[M-H]-	161.522	31661259
DeepCCS	[M+H]+	169.346	30932474
DeepCCS	[M-H]-	165.894	30932474
DeepCCS	[M-2H]-	201.842	30932474
DeepCCS	[M+Na]+	178.132	30932474
AllCCS	[M+H]+	165.4	32859911
AllCCS	[M+H-H2O]+	161.8	32859911
AllCCS	[M+NH4]+	168.7	32859911
AllCCS	[M+Na]+	169.6	32859911
AllCCS	[M-H]-	168.4	32859911
AllCCS	[M+Na-2H]-	169.3	32859911
AllCCS	[M+HCOO]-	170.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-5-pentyl-2-furanpentanoic acid	CCCCCC1=CC(C)=C(CCCCC(O)=O)O1	2990.6	Standard polar	33892256
3-Methyl-5-pentyl-2-furanpentanoic acid	CCCCCC1=CC(C)=C(CCCCC(O)=O)O1	1888.3	Standard non polar	33892256
3-Methyl-5-pentyl-2-furanpentanoic acid	CCCCCC1=CC(C)=C(CCCCC(O)=O)O1	1921.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methyl-5-pentyl-2-furanpentanoic acid,1TMS,isomer #1	CCCCCC1=CC(C)=C(CCCCC(=O)O[Si](C)(C)C)O1	2001.6	Semi standard non polar	33892256
3-Methyl-5-pentyl-2-furanpentanoic acid,1TBDMS,isomer #1	CCCCCC1=CC(C)=C(CCCCC(=O)O[Si](C)(C)C(C)(C)C)O1	2221.9	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-Methyl-5-pentyl-2-furanpentanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-062i-9520000000-3ebbfb4b72671a3d1532	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic 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-furanpentanoic acid 10V, Positive-QTOF	splash10-000i-0090000000-8927f5968b546862b3cb	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 20V, Positive-QTOF	splash10-0pb9-9880000000-cc40240697e41611f9c9	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 40V, Positive-QTOF	splash10-0k96-9500000000-817f09003190e3604b2f	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 10V, Negative-QTOF	splash10-0udi-0090000000-6c3ca79f4a77863876c4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 20V, Negative-QTOF	splash10-0zgi-1490000000-08bbbeb1441065c4b716	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 40V, Negative-QTOF	splash10-0a4i-6900000000-b1886890907b321b8c36	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 10V, Negative-QTOF	splash10-0udi-0090000000-cce227597bc03fb5e702	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 20V, Negative-QTOF	splash10-0udi-2490000000-803cc38dddbb289a0214	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 40V, Negative-QTOF	splash10-05fs-3900000000-e1b45ebbd4ac01956f45	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 10V, Positive-QTOF	splash10-0udi-1290000000-05d87f28373e4e2c43e1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 20V, Positive-QTOF	splash10-0udr-5980000000-2ffd546e858b7732e56d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methyl-5-pentyl-2-furanpentanoic acid 40V, Positive-QTOF	splash10-0a4l-9300000000-6cca901aaf8fc15aa3c1	2021-09-22	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

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

54171982

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

Vetter W, Wendlinger C (2013). Furan fatty acids – valuable minor fatty acids in food. Lipid Technology.
Wendlinger C, Hammann S, Vetter W (2016). Detailed Study of Furan Fatty Acids in Total Lipids and the Cholesteryl Ester Fraction of Fish Liver. Food Analytical Methods.

Showing metabocard for 3-Methyl-5-pentyl-2-furanpentanoic acid (HMDB0112086)

MOL for HMDB0112086 (3-Methyl-5-pentyl-2-furanpentanoic acid)

3D MOL for HMDB0112086 (3-Methyl-5-pentyl-2-furanpentanoic acid)

3D SDF for HMDB0112086 (3-Methyl-5-pentyl-2-furanpentanoic acid)

3D-SDF for HMDB0112086 (3-Methyl-5-pentyl-2-furanpentanoic acid)

PDB for HMDB0112086 (3-Methyl-5-pentyl-2-furanpentanoic acid)

3D PDB for HMDB0112086 (3-Methyl-5-pentyl-2-furanpentanoic acid)

SMILES for HMDB0112086 (3-Methyl-5-pentyl-2-furanpentanoic acid)

INCHI for HMDB0112086 (3-Methyl-5-pentyl-2-furanpentanoic acid)

Structure for HMDB0112086 (3-Methyl-5-pentyl-2-furanpentanoic acid)

3D Structure for HMDB0112086 (3-Methyl-5-pentyl-2-furanpentanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra