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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-08 16:17:34 UTC

Update Date

2022-03-07 03:18:04 UTC

HMDB ID

HMDB0112085

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,4-Dimethyl-5-pentyl-2-furanpentanoic acid

Description

3,4-Dimethyl-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. 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid, in particular, can be described by the shorthand notation 5D5. This refers to its 5-carbon carboxyalkyl moiety, the dimethyl substitutions in the 3- and 4-positions 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

HMDB0112085
     RDKit          3D
3,4-Dimethyl-5-pentyl-2-furanpentanoic acid
 45 45  0  0  0  0  0  0  0  0999 V2000
    4.9453    1.2425    0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105    0.3152    1.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4127   -0.5244    1.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999   -1.5207    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6878   -1.1800   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3510   -0.5058   -0.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377   -1.1803   -1.1898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8036   -0.3982   -1.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831   -0.8403   -1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -0.8812   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4427   -1.3300   -0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2277   -1.3418    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2901   -0.0109    1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0116    0.9084    0.8803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    0.2468    2.4492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4120    0.8962   -1.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619    2.1099   -0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    0.7903   -0.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8007    1.9754   -0.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4264    2.2274    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0344    0.8277   -0.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0435    1.5775    0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008    0.9002    2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633   -0.3205    1.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    0.1132    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5176   -1.1214    2.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0774   -2.1373    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354   -2.3646    1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6762   -2.1116   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4419   -0.5520   -1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1379   -1.8730   -1.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422   -0.2184   -2.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5935   -1.6209    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1038    0.1350    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9556   -0.7436   -1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3639   -2.4177   -0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2792   -1.7027    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8095   -2.0826    1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9241    0.4652    3.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986    2.0194   -1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7118    3.0192   -1.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6541    2.3310    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354    2.9196   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309    1.9704   -1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801    1.9893    0.5648 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  8 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  6  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
M  END


  Mrv1652309071721522D          

 19 19  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
   10.2681    1.2376    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
  4  1  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
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13 12  1  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
 15 13  2  0  0  0  0
 16 11  1  0  0  0  0
 17 16  2  0  0  0  0
 18 16  1  0  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0112085

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O3/c1-4-5-6-9-14-12(2)13(3)15(19-14)10-7-8-11-16(17)18/h4-11H2,1-3H3,(H,17,18)

> <INCHI_KEY>
IVHFOCAFZRRFIX-UHFFFAOYSA-N

> <FORMULA>
C16H26O3

> <MOLECULAR_WEIGHT>
266.381

> <EXACT_MASS>
266.188194697

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.825734948517265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(3,4-dimethyl-5-pentylfuran-2-yl)pentanoic acid

> <ALOGPS_LOGP>
4.69

> <JCHEM_LOGP>
4.931671776

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.826950925080986

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5779473995092594

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
77.2726

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(3,4-dimethyl-5-pentylfuran-2-yl)pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0112085
     RDKit          3D
3,4-Dimethyl-5-pentyl-2-furanpentanoic acid
 45 45  0  0  0  0  0  0  0  0999 V2000
    4.9453    1.2425    0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105    0.3152    1.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4127   -0.5244    1.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999   -1.5207    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6878   -1.1800   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3510   -0.5058   -0.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377   -1.1803   -1.1898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8036   -0.3982   -1.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831   -0.8403   -1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -0.8812   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4427   -1.3300   -0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2277   -1.3418    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2901   -0.0109    1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0116    0.9084    0.8803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    0.2468    2.4492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4120    0.8962   -1.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619    2.1099   -0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    0.7903   -0.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8007    1.9754   -0.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4264    2.2274    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0344    0.8277   -0.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0435    1.5775    0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008    0.9002    2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633   -0.3205    1.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    0.1132    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5176   -1.1214    2.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0774   -2.1373    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354   -2.3646    1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6762   -2.1116   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4419   -0.5520   -1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1379   -1.8730   -1.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422   -0.2184   -2.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5935   -1.6209    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1038    0.1350    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9556   -0.7436   -1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3639   -2.4177   -0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2792   -1.7027    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8095   -2.0826    1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9241    0.4652    3.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986    2.0194   -1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7118    3.0192   -1.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6541    2.3310    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354    2.9196   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309    1.9704   -1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801    1.9893    0.5648 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  8 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  6  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  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      19.167   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.925   4.800   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.181  -2.320   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.650  -2.159   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.023  -0.752   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.531   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.197   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.492  -0.591   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.865   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.863   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.636   2.149   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.605   3.294   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.866   0.816   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.198   2.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.530   3.437   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.196   2.667   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.530   4.977   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      15.359   1.136   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    9                                                       
CONECT    7    8   10                                                       
CONECT    8    7   11                                                       
CONECT    9    6   14                                                       
CONECT   10    7   15                                                       
CONECT   11    8   16                                                       
CONECT   12    2   13   14                                                  
CONECT   13    3   12   15                                                  
CONECT   14    9   12   19                                                  
CONECT   15   10   13   19                                                  
CONECT   16   11   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0112085
HETATM    1  C1  UNL     1       4.945   1.243   0.495  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.611   0.315   1.561  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.413  -0.524   1.612  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.100  -1.521   0.604  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.688  -1.180  -0.752  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.351  -0.506  -0.897  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.238  -1.180  -1.190  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.804  -0.398  -1.260  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.183  -0.840  -1.566  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.043  -0.881  -0.322  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.443  -1.330  -0.614  1.00  0.00           C  
HETATM   12  C11 UNL     1      -5.228  -1.342   0.687  1.00  0.00           C  
HETATM   13  C12 UNL     1      -5.290  -0.011   1.324  1.00  0.00           C  
HETATM   14  O2  UNL     1      -6.012   0.908   0.880  1.00  0.00           O  
HETATM   15  O3  UNL     1      -4.534   0.247   2.449  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.412   0.896  -1.005  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.262   2.110  -0.981  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.974   0.790  -0.778  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.801   1.975  -0.499  1.00  0.00           C  
HETATM   20  H1  UNL     1       4.426   2.227   0.516  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.034   0.828  -0.519  1.00  0.00           H  
HETATM   22  H3  UNL     1       6.043   1.577   0.695  1.00  0.00           H  
HETATM   23  H4  UNL     1       4.601   0.900   2.563  1.00  0.00           H  
HETATM   24  H5  UNL     1       5.563  -0.320   1.747  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.501   0.113   1.902  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.518  -1.121   2.608  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.077  -2.137   0.476  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.435  -2.365   1.040  1.00  0.00           H  
HETATM   29  H10 UNL     1       2.676  -2.112  -1.437  1.00  0.00           H  
HETATM   30  H11 UNL     1       3.442  -0.552  -1.259  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.138  -1.873  -1.961  1.00  0.00           H  
HETATM   32  H13 UNL     1      -2.642  -0.218  -2.370  1.00  0.00           H  
HETATM   33  H14 UNL     1      -2.593  -1.621   0.366  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.104   0.135   0.116  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.956  -0.744  -1.378  1.00  0.00           H  
HETATM   36  H17 UNL     1      -4.364  -2.418  -0.913  1.00  0.00           H  
HETATM   37  H18 UNL     1      -6.279  -1.703   0.488  1.00  0.00           H  
HETATM   38  H19 UNL     1      -4.810  -2.083   1.394  1.00  0.00           H  
HETATM   39  H20 UNL     1      -4.924   0.465   3.357  1.00  0.00           H  
HETATM   40  H21 UNL     1      -2.099   2.019  -1.735  1.00  0.00           H  
HETATM   41  H22 UNL     1      -0.712   3.019  -1.306  1.00  0.00           H  
HETATM   42  H23 UNL     1      -1.654   2.331   0.031  1.00  0.00           H  
HETATM   43  H24 UNL     1       1.235   2.920  -0.732  1.00  0.00           H  
HETATM   44  H25 UNL     1       2.731   1.970  -1.133  1.00  0.00           H  
HETATM   45  H26 UNL     1       2.080   1.989   0.565  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   18   18
CONECT    7    8
CONECT    8    9   16   16
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   35   36
CONECT   12   13   37   38
CONECT   13   14   14   15
CONECT   15   39
CONECT   16   17   18
CONECT   17   40   41   42
CONECT   18   19
CONECT   19   43   44   45
END

HMDB0112085
     RDKit          3D
3,4-Dimethyl-5-pentyl-2-furanpentanoic acid
 45 45  0  0  0  0  0  0  0  0999 V2000
    4.9453    1.2425    0.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105    0.3152    1.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4127   -0.5244    1.6124 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999   -1.5207    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6878   -1.1800   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3510   -0.5058   -0.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377   -1.1803   -1.1898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8036   -0.3982   -1.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1831   -0.8403   -1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -0.8812   -0.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4427   -1.3300   -0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2277   -1.3418    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2901   -0.0109    1.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0116    0.9084    0.8803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5340    0.2468    2.4492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4120    0.8962   -1.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619    2.1099   -0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    0.7903   -0.7777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8007    1.9754   -0.4986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4264    2.2274    0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0344    0.8277   -0.5194 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0435    1.5775    0.6949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6008    0.9002    2.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5633   -0.3205    1.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    0.1132    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5176   -1.1214    2.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0774   -2.1373    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354   -2.3646    1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6762   -2.1116   -1.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4419   -0.5520   -1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1379   -1.8730   -1.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422   -0.2184   -2.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5935   -1.6209    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1038    0.1350    0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9556   -0.7436   -1.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3639   -2.4177   -0.9128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2792   -1.7027    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8095   -2.0826    1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9241    0.4652    3.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986    2.0194   -1.7348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7118    3.0192   -1.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6541    2.3310    0.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354    2.9196   -0.7315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309    1.9704   -1.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0801    1.9893    0.5648 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  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
  8 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18  6  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-Dimethyl-5-pentyl-2-furanpentanoate	Generator
5-(3,4-Dimethyl-5-pentylfuran-2-yl)-pentanoate	HMDB
5D5	HMDB
DiMe(5,5)	HMDB
5-(3,4-Dimethyl-5-pentyl-2-furyl)pentanoic acid	HMDB
6,9-Epoxy-7,8-dimethyl-6,8-tetradecadienoic acid	HMDB
6,9-Epoxy-7,8-dimethyltetradeca-6,8-dienoic acid	HMDB
5-(3,4-Dimethyl-5-pentylfuran-2-yl)pentanoic acid	HMDB
5-(3,4-Dimethyl-5-pentylfuran-2-yl)pentanoate	HMDB
3,4-dimethyl-5-pentyl-2-furanpentanoic acid	SMPDB

Chemical Formula

C₁₆H₂₆O₃

Average Molecular Weight

266.381

Monoisotopic Molecular Weight

266.188194697

IUPAC Name

5-(3,4-dimethyl-5-pentylfuran-2-yl)pentanoic acid

Traditional Name

5-(3,4-dimethyl-5-pentylfuran-2-yl)pentanoic acid

CAS Registry Number

116627-36-2

SMILES

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

InChI Identifier

InChI=1S/C16H26O3/c1-4-5-6-9-14-12(2)13(3)15(19-14)10-7-8-11-16(17)18/h4-11H2,1-3H3,(H,17,18)

InChI Key

IVHFOCAFZRRFIX-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

Exogenous (HMDB: HMDB0112085)

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	4.69	ALOGPS
logP	4.93	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.83	ChemAxon
pKa (Strongest Basic)	-2.6	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	77.27 m³·mol⁻¹	ChemAxon
Polarizability	32.83 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]+	167.342	31661259
DarkChem	[M-H]-	163.924	31661259
DeepCCS	[M+H]+	173.968	30932474
DeepCCS	[M-H]-	171.495	30932474
DeepCCS	[M-2H]-	205.102	30932474
DeepCCS	[M+Na]+	181.391	30932474
AllCCS	[M+H]+	169.6	32859911
AllCCS	[M+H-H2O]+	166.1	32859911
AllCCS	[M+NH4]+	172.7	32859911
AllCCS	[M+Na]+	173.6	32859911
AllCCS	[M-H]-	172.6	32859911
AllCCS	[M+Na-2H]-	173.5	32859911
AllCCS	[M+HCOO]-	174.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	8.43 minutes	32390414
Predicted by Siyang on May 30, 2022	20.6331 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.95 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2300.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	630.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	239.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	353.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	482.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	824.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	928.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	124.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1841.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	668.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2092.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	610.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	458.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	437.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	503.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dimethyl-5-pentyl-2-furanpentanoic acid	CCCCCC1=C(C)C(C)=C(CCCCC(O)=O)O1	3021.9	Standard polar	33892256
3,4-Dimethyl-5-pentyl-2-furanpentanoic acid	CCCCCC1=C(C)C(C)=C(CCCCC(O)=O)O1	1956.9	Standard non polar	33892256
3,4-Dimethyl-5-pentyl-2-furanpentanoic acid	CCCCCC1=C(C)C(C)=C(CCCCC(O)=O)O1	2022.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dimethyl-5-pentyl-2-furanpentanoic acid,1TMS,isomer #1	CCCCCC1=C(C)C(C)=C(CCCCC(=O)O[Si](C)(C)C)O1	2094.5	Semi standard non polar	33892256
3,4-Dimethyl-5-pentyl-2-furanpentanoic acid,1TBDMS,isomer #1	CCCCCC1=C(C)C(C)=C(CCCCC(=O)O[Si](C)(C)C(C)(C)C)O1	2332.7	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 - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9331000000-2c88911e04104001bc6d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dimethyl-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 - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 10V, Positive-QTOF	splash10-0002-0090000000-09bacb5670ef78369012	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 20V, Positive-QTOF	splash10-0avj-8790000000-199bea84e92f52a86683	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 40V, Positive-QTOF	splash10-05mn-9600000000-07a4c3a1252fb11cfa94	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 10V, Negative-QTOF	splash10-014i-0090000000-bee28f60c8f9d5f9eeef	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 20V, Negative-QTOF	splash10-014j-1390000000-19967d19990e706d16ab	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 40V, Negative-QTOF	splash10-0a4i-5920000000-46983834dc74cbe2d16f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 10V, Positive-QTOF	splash10-014j-0290000000-b3d1be67593a13fa5ed6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 20V, Positive-QTOF	splash10-0092-1940000000-27c33a9815aa542e6f57	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 40V, Positive-QTOF	splash10-0a4l-9300000000-302fd3c00c1e0f58203a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 10V, Negative-QTOF	splash10-00kb-0090000000-f4b69762fb09a389b5cf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 20V, Negative-QTOF	splash10-014j-1290000000-b4fa5377d3ab0b5909ae	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid 40V, Negative-QTOF	splash10-00ds-1910000000-0e8e20447c1f6da6db63	2021-09-24	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

74849741

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85564651

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 3,4-Dimethyl-5-pentyl-2-furanpentanoic acid (HMDB0112085)

MOL for HMDB0112085 (3,4-Dimethyl-5-pentyl-2-furanpentanoic acid)

3D MOL for HMDB0112085 (3,4-Dimethyl-5-pentyl-2-furanpentanoic acid)

3D SDF for HMDB0112085 (3,4-Dimethyl-5-pentyl-2-furanpentanoic acid)

3D-SDF for HMDB0112085 (3,4-Dimethyl-5-pentyl-2-furanpentanoic acid)

PDB for HMDB0112085 (3,4-Dimethyl-5-pentyl-2-furanpentanoic acid)

3D PDB for HMDB0112085 (3,4-Dimethyl-5-pentyl-2-furanpentanoic acid)

SMILES for HMDB0112085 (3,4-Dimethyl-5-pentyl-2-furanpentanoic acid)

INCHI for HMDB0112085 (3,4-Dimethyl-5-pentyl-2-furanpentanoic acid)

Structure for HMDB0112085 (3,4-Dimethyl-5-pentyl-2-furanpentanoic acid)

3D Structure for HMDB0112085 (3,4-Dimethyl-5-pentyl-2-furanpentanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra