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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-08 16:19:45 UTC

Update Date

2022-03-07 03:18:04 UTC

HMDB ID

HMDB0112097

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Butyl-2-furanoctanoic acid

Description

5-Butyl-2-furanoctanoic 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. 5-Butyl-2-furanoctanoic acid, in particular, can be described by the shorthand notation 8F4. This refers to its 8-carbon carboxyalkyl moiety, the non-methylated furan moiety, and its 4-carbon alkyl moiety. It has been identified in carp.

Structure

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

HMDB0112097
     RDKit          3D
5-Butyl-2-furanoctanoic acid
 45 45  0  0  0  0  0  0  0  0999 V2000
    4.1832    2.1158   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5565    1.6908    0.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4648    0.7255    1.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7278   -0.5220    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4865   -1.2835    0.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5187   -2.4594   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090   -2.8859   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4395   -1.9679    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0507   -2.0481    0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7563   -1.3239   -0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2387   -1.4542   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0938   -0.8013   -1.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8664    0.6746   -1.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1264    1.4445   -0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5081    1.3540    0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5614    1.8358   -0.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2781    2.2880   -1.7199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8985    1.8073   -0.2204 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -1.0363    0.8897 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2735    2.2764   -0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485    1.3046   -1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776    3.0040   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    2.5912    1.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5696    1.2563    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3748    1.2207    1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.3992    2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1823   -0.1696   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4677   -1.1856    1.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510   -2.9701   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890   -3.7886   -0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3546   -3.1136    0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3024   -1.6067    1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4888   -1.8665   -1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075   -0.2963   -0.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4865   -2.5474   -0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370   -1.0900    0.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359   -1.0771   -1.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208   -1.2558   -2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3766    1.1035   -2.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669    0.8055   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4162    1.2133    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9496    2.5334   -0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5412    2.0369    1.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7498    0.3458    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3464    2.7227   -0.1177 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  8 19  1  0
 19  5  1  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
  6 29  1  0
  7 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
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 18 45  1  0
M  END

  Mrv1652309081718192D          

 19 19  0  0  0  0            999 V2000
   -2.8384   -1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3535   -1.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5330   -1.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9360   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2215    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6505    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3649   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0481   -0.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7926    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849   -1.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9919   -1.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2276   -0.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0781   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7939   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5083    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7939   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244    0.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  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>
HMDB0112097

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC1=CC=C(CCCCCCCC(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O3/c1-2-3-9-14-12-13-15(19-14)10-7-5-4-6-8-11-16(17)18/h12-13H,2-11H2,1H3,(H,17,18)

> <INCHI_KEY>
JIZXCHDGGWLYFG-UHFFFAOYSA-N

> <FORMULA>
C16H26O3

> <MOLECULAR_WEIGHT>
266.381

> <EXACT_MASS>
266.188194697

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.96432013042383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(5-butylfuran-2-yl)octanoic acid

> <ALOGPS_LOGP>
5.24

> <JCHEM_LOGP>
4.793966327333334

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.949762389405608

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7575078298663342

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
76.3922

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(5-butylfuran-2-yl)octanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0112097
     RDKit          3D
5-Butyl-2-furanoctanoic acid
 45 45  0  0  0  0  0  0  0  0999 V2000
    4.1832    2.1158   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5565    1.6908    0.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4648    0.7255    1.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7278   -0.5220    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4865   -1.2835    0.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5187   -2.4594   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090   -2.8859   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4395   -1.9679    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0507   -2.0481    0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7563   -1.3239   -0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2387   -1.4542   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0938   -0.8013   -1.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8664    0.6746   -1.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1264    1.4445   -0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5081    1.3540    0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5614    1.8358   -0.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2781    2.2880   -1.7199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8985    1.8073   -0.2204 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -1.0363    0.8897 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2735    2.2764   -0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485    1.3046   -1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776    3.0040   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    2.5912    1.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5696    1.2563    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3748    1.2207    1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.3992    2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1823   -0.1696   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4677   -1.1856    1.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510   -2.9701   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890   -3.7886   -0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3546   -3.1136    0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3024   -1.6067    1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4888   -1.8665   -1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075   -0.2963   -0.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4865   -2.5474   -0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370   -1.0900    0.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359   -1.0771   -1.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208   -1.2558   -2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3766    1.1035   -2.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669    0.8055   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4162    1.2133    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9496    2.5334   -0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5412    2.0369    1.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7498    0.3458    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3464    2.7227   -0.1177 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  8 19  1  0
 19  5  1  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
  6 29  1  0
  7 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
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 18 45  1  0
M  END

HEADER    PROTEIN                                 08-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-17         0                                  
HETATM    1  C   UNK     0      -5.298  -3.252   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.393  -2.006   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.862  -2.167   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.347  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.013   0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.681   0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.015  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.956  -0.921   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.346   0.206   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.348   0.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.345  -2.415   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.851  -2.095   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.425  -1.082   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.012  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.682  -0.564   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.016   0.206   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.682  -2.104   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.606   0.063   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    9                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   10                                                       
CONECT    8    6   11                                                       
CONECT    9    3   14                                                       
CONECT   10    7   15                                                       
CONECT   11    8   16                                                       
CONECT   12   13   14                                                       
CONECT   13   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    HMDB0112097
HETATM    1  C1  UNL     1       4.183   2.116  -0.361  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.556   1.691   0.960  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.465   0.725   1.650  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.728  -0.522   0.844  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.486  -1.284   0.552  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.519  -2.459  -0.187  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.209  -2.886  -0.259  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.439  -1.968   0.427  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.051  -2.048   0.597  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.756  -1.324  -0.550  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.239  -1.454  -0.300  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.094  -0.801  -1.328  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.866   0.675  -1.462  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.126   1.445  -0.217  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.508   1.354   0.326  1.00  0.00           C  
HETATM   16  C16 UNL     1      -5.561   1.836  -0.584  1.00  0.00           C  
HETATM   17  O1  UNL     1      -5.278   2.288  -1.720  1.00  0.00           O  
HETATM   18  O2  UNL     1      -6.899   1.807  -0.220  1.00  0.00           O  
HETATM   19  O3  UNL     1       2.241  -1.036   0.890  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.273   2.276  -0.258  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.049   1.305  -1.103  1.00  0.00           H  
HETATM   22  H3  UNL     1       3.678   3.004  -0.765  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.471   2.591   1.613  1.00  0.00           H  
HETATM   24  H5  UNL     1       2.570   1.256   0.751  1.00  0.00           H  
HETATM   25  H6  UNL     1       5.375   1.221   1.989  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.926   0.399   2.588  1.00  0.00           H  
HETATM   27  H8  UNL     1       5.182  -0.170  -0.128  1.00  0.00           H  
HETATM   28  H9  UNL     1       5.468  -1.186   1.320  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.351  -2.970  -0.628  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.889  -3.789  -0.775  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.355  -3.114   0.623  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.302  -1.607   1.579  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.489  -1.866  -1.479  1.00  0.00           H  
HETATM   34  H15 UNL     1      -0.407  -0.296  -0.648  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.487  -2.547  -0.309  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.537  -1.090   0.695  1.00  0.00           H  
HETATM   37  H18 UNL     1      -4.136  -1.077  -1.150  1.00  0.00           H  
HETATM   38  H19 UNL     1      -2.821  -1.256  -2.323  1.00  0.00           H  
HETATM   39  H20 UNL     1      -3.377   1.103  -2.344  1.00  0.00           H  
HETATM   40  H21 UNL     1      -1.767   0.805  -1.690  1.00  0.00           H  
HETATM   41  H22 UNL     1      -2.416   1.213   0.591  1.00  0.00           H  
HETATM   42  H23 UNL     1      -2.950   2.533  -0.462  1.00  0.00           H  
HETATM   43  H24 UNL     1      -4.541   2.037   1.227  1.00  0.00           H  
HETATM   44  H25 UNL     1      -4.750   0.346   0.750  1.00  0.00           H  
HETATM   45  H26 UNL     1      -7.346   2.723  -0.118  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    6   19
CONECT    6    7   29
CONECT    7    8    8   30
CONECT    8    9   19
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   35   36
CONECT   12   13   37   38
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16   43   44
CONECT   16   17   17   18
CONECT   18   45
END

HMDB0112097
     RDKit          3D
5-Butyl-2-furanoctanoic acid
 45 45  0  0  0  0  0  0  0  0999 V2000
    4.1832    2.1158   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5565    1.6908    0.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4648    0.7255    1.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7278   -0.5220    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4865   -1.2835    0.5518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5187   -2.4594   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090   -2.8859   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4395   -1.9679    0.4268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0507   -2.0481    0.5966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7563   -1.3239   -0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2387   -1.4542   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0938   -0.8013   -1.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8664    0.6746   -1.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1264    1.4445   -0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5081    1.3540    0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5614    1.8358   -0.5840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2781    2.2880   -1.7199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8985    1.8073   -0.2204 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -1.0363    0.8897 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2735    2.2764   -0.2582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0485    1.3046   -1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776    3.0040   -0.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    2.5912    1.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5696    1.2563    0.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3748    1.2207    1.9894 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9264    0.3992    2.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1823   -0.1696   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4677   -1.1856    1.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3510   -2.9701   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8890   -3.7886   -0.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3546   -3.1136    0.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3024   -1.6067    1.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4888   -1.8665   -1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075   -0.2963   -0.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4865   -2.5474   -0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370   -1.0900    0.6952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359   -1.0771   -1.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208   -1.2558   -2.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3766    1.1035   -2.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7669    0.8055   -1.6904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4162    1.2133    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9496    2.5334   -0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5412    2.0369    1.2269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7498    0.3458    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3464    2.7227   -0.1177 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
  8 19  1  0
 19  5  1  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
  6 29  1  0
  7 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
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  0
 15 44  1  0
 18 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Butyl-2-furanoctanoate	Generator
8F4	HMDB
8-(5-Butyl-2-furyl)octanoic acid	HMDB
9,12-Epoxy-9,11-hexadecadienoic acid	HMDB
9,12-Epoxyhexadeca-9,11-dienoic acid	HMDB
8-(5-Butylfuran-2-yl)octanoic acid	HMDB
8-(5-Butylfuran-2-yl)octanoate	HMDB
5-butyl-2-furanoctanoic acid	SMPDB

Chemical Formula

C₁₆H₂₆O₃

Average Molecular Weight

266.381

Monoisotopic Molecular Weight

266.188194697

IUPAC Name

8-(5-butylfuran-2-yl)octanoic acid

Traditional Name

8-(5-butylfuran-2-yl)octanoic acid

CAS Registry Number

Not Available

SMILES

CCCCC1=CC=C(CCCCCCCC(O)=O)O1

InChI Identifier

InChI=1S/C16H26O3/c1-2-3-9-14-12-13-15(19-14)10-7-5-4-6-8-11-16(17)18/h12-13H,2-11H2,1H3,(H,17,18)

InChI Key

JIZXCHDGGWLYFG-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: HMDB0112097)

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	5.24	ALOGPS
logP	4.79	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-2.8	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	11	ChemAxon
Refractivity	76.39 m³·mol⁻¹	ChemAxon
Polarizability	32.96 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]+	165.836	31661259
DarkChem	[M-H]-	166.826	31661259
DeepCCS	[M+H]+	171.12	30932474
DeepCCS	[M-H]-	167.357	30932474
DeepCCS	[M-2H]-	203.716	30932474
DeepCCS	[M+Na]+	179.935	30932474
AllCCS	[M+H]+	169.8	32859911
AllCCS	[M+H-H2O]+	166.4	32859911
AllCCS	[M+NH4]+	173.0	32859911
AllCCS	[M+Na]+	173.9	32859911
AllCCS	[M-H]-	173.3	32859911
AllCCS	[M+Na-2H]-	174.3	32859911
AllCCS	[M+HCOO]-	175.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Butyl-2-furanoctanoic acid	CCCCC1=CC=C(CCCCCCCC(O)=O)O1	3187.1	Standard polar	33892256
5-Butyl-2-furanoctanoic acid	CCCCC1=CC=C(CCCCCCCC(O)=O)O1	2026.5	Standard non polar	33892256
5-Butyl-2-furanoctanoic acid	CCCCC1=CC=C(CCCCCCCC(O)=O)O1	2036.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Butyl-2-furanoctanoic acid,1TMS,isomer #1	CCCCC1=CC=C(CCCCCCCC(=O)O[Si](C)(C)C)O1	2148.6	Semi standard non polar	33892256
5-Butyl-2-furanoctanoic acid,1TBDMS,isomer #1	CCCCC1=CC=C(CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O1	2389.3	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 - 5-Butyl-2-furanoctanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00g0-8931000000-c1a125d2a21cd650f67c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Butyl-2-furanoctanoic 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 - 5-Butyl-2-furanoctanoic acid 10V, Positive-QTOF	splash10-0002-0090000000-f66dc985bbe78d8f7f76	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyl-2-furanoctanoic acid 20V, Positive-QTOF	splash10-00ym-7690000000-79b4cb22f041f3fdbfc8	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyl-2-furanoctanoic acid 40V, Positive-QTOF	splash10-0006-9300000000-4c9d62d52dd05b0558cc	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyl-2-furanoctanoic acid 10V, Negative-QTOF	splash10-014i-0090000000-c1528f7334cba7100949	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyl-2-furanoctanoic acid 20V, Negative-QTOF	splash10-01ba-1290000000-160f58ce2a8064837c22	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyl-2-furanoctanoic acid 40V, Negative-QTOF	splash10-0a4l-9420000000-4ccbadc44b0d0ca411f5	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyl-2-furanoctanoic acid 10V, Negative-QTOF	splash10-014i-0090000000-74f489a16f7b0d4ad478	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyl-2-furanoctanoic acid 20V, Negative-QTOF	splash10-014i-0290000000-2dd520a3a66ba0a63e7b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyl-2-furanoctanoic acid 40V, Negative-QTOF	splash10-0006-8910000000-0752bdcff929d7e8ebd2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyl-2-furanoctanoic acid 10V, Positive-QTOF	splash10-00l2-3590000000-6c3513979baa63e124bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyl-2-furanoctanoic acid 20V, Positive-QTOF	splash10-0032-9520000000-3ac3e615cf01624fceee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Butyl-2-furanoctanoic acid 40V, Positive-QTOF	splash10-05o4-9200000000-e7d30a638308ae1d195e	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

74849752

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131819627

PDB ID

Not Available

ChEBI ID

169011

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 5-Butyl-2-furanoctanoic acid (HMDB0112097)

MOL for HMDB0112097 (5-Butyl-2-furanoctanoic acid)

3D MOL for HMDB0112097 (5-Butyl-2-furanoctanoic acid)

3D SDF for HMDB0112097 (5-Butyl-2-furanoctanoic acid)

3D-SDF for HMDB0112097 (5-Butyl-2-furanoctanoic acid)

PDB for HMDB0112097 (5-Butyl-2-furanoctanoic acid)

3D PDB for HMDB0112097 (5-Butyl-2-furanoctanoic acid)

SMILES for HMDB0112097 (5-Butyl-2-furanoctanoic acid)

INCHI for HMDB0112097 (5-Butyl-2-furanoctanoic acid)

Structure for HMDB0112097 (5-Butyl-2-furanoctanoic acid)

3D Structure for HMDB0112097 (5-Butyl-2-furanoctanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra