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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-09-08 16:20:43 UTC

Update Date

2022-03-07 03:18:05 UTC

HMDB ID

HMDB0112102

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-pentyl-2-furannonanoic acid

Description

5-pentyl-2-furannonanoic 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-pentyl-2-furannonanoic acid, in particular, can be described by the shorthand notation 9F5. This refers to its 9-carbon carboxyalkyl moiety, the non-methylated furan moiety, and its 5-carbon alkyl moiety. It has been identified in carp.

Structure

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

HMDB0112102
     RDKit          3D
5-pentyl-2-furannonanoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    4.9462    2.6112   -0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2017    1.6073   -1.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112    0.2507   -1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2481   -0.2439    0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7189   -1.6180    0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2655   -1.6227    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5772   -1.3939    1.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2458   -1.5074    1.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1656   -1.8021    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0356   -2.0297   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5017   -0.7386   -1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7049   -0.8418   -1.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9297   -1.3771   -1.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838   -0.5388   -0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7065    0.8507   -0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563    1.6798    0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3906    1.1422    1.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4929    1.1225    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6156    0.2158   -0.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4378    2.1297    0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3895   -1.8615   -0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3120    3.5920   -0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8594    2.6431   -0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5038    2.3984    0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7756    1.9973   -2.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3102    1.5099   -1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5136    0.3806   -0.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311   -0.4107   -1.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3308   -0.3021    0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9499    0.4484    1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0232   -2.3294   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1956   -1.8520    1.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0236   -1.1663    2.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133   -1.3885    2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312   -2.4571    0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2066   -2.8098   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224   -0.3173   -1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806   -0.0192   -0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9450    0.1646   -2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5032   -1.4855   -2.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667   -2.4348   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577   -1.3135   -2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6611   -0.5510    0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3069   -1.0199    0.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7900    1.3618   -0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4978    0.8203   -1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3061    2.7393    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863    1.6824    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2215    0.1087    1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6864    1.8329    2.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2450    2.1431    0.9548 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  2  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  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9 21  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 20 51  1  0
M  END


  Mrv1652309081718202D          

 21 21  0  0  0  0            999 V2000
   17.0156   -0.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6801    0.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8596    0.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6169    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9024    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3314    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1880    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5240    1.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0458    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4735    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7035    1.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7603    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7590    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7805    2.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2285    3.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3680    1.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4748    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0445    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3301    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0445    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5610    2.0374    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  3  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  9  1  0  0  0  0
 13 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  2  0  0  0  0
 17 12  1  0  0  0  0
 17 15  2  0  0  0  0
 18 13  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 21 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0112102

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O3/c1-2-3-8-11-16-14-15-17(21-16)12-9-6-4-5-7-10-13-18(19)20/h14-15H,2-13H2,1H3,(H,19,20)

> <INCHI_KEY>
BJTONYHCPUUWFX-UHFFFAOYSA-N

> <FORMULA>
C18H30O3

> <MOLECULAR_WEIGHT>
294.435

> <EXACT_MASS>
294.219494826

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.2616409557836

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-(5-pentylfuran-2-yl)nonanoic acid

> <ALOGPS_LOGP>
6.09

> <JCHEM_LOGP>
5.683103657333334

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.834774650263049

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7575136626571815

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
85.5942

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(5-pentylfuran-2-yl)nonanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0112102
     RDKit          3D
5-pentyl-2-furannonanoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    4.9462    2.6112   -0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2017    1.6073   -1.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112    0.2507   -1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2481   -0.2439    0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7189   -1.6180    0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2655   -1.6227    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5772   -1.3939    1.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2458   -1.5074    1.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1656   -1.8021    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0356   -2.0297   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5017   -0.7386   -1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7049   -0.8418   -1.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9297   -1.3771   -1.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838   -0.5388   -0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7065    0.8507   -0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563    1.6798    0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3906    1.1422    1.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4929    1.1225    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6156    0.2158   -0.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4378    2.1297    0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3895   -1.8615   -0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3120    3.5920   -0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8594    2.6431   -0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5038    2.3984    0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7756    1.9973   -2.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3102    1.5099   -1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5136    0.3806   -0.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311   -0.4107   -1.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3308   -0.3021    0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9499    0.4484    1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0232   -2.3294   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1956   -1.8520    1.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0236   -1.1663    2.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133   -1.3885    2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312   -2.4571    0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2066   -2.8098   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224   -0.3173   -1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806   -0.0192   -0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9450    0.1646   -2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5032   -1.4855   -2.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667   -2.4348   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577   -1.3135   -2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6611   -0.5510    0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3069   -1.0199    0.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7900    1.3618   -0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4978    0.8203   -1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3061    2.7393    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863    1.6824    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2215    0.1087    1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6864    1.8329    2.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2450    2.1431    0.9548 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  2  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  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9 21  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 20 51  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      31.763  -1.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.136   0.347   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.605   0.508   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.818   5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.485   6.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.152   6.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.151   5.335   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.978   1.915   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.486   5.335   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.817   6.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      27.447   2.076   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.819   6.105   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.483   5.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.590   4.817   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.560   5.961   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.820   3.483   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.153   5.335   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.150   6.105   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.816   5.335   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.150   7.645   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      25.314   3.803   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8    3   11                                                       
CONECT    9    6   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   16                                                       
CONECT   12    9   17                                                       
CONECT   13   10   18                                                       
CONECT   14   15   16                                                       
CONECT   15   14   17                                                       
CONECT   16   11   14   21                                                  
CONECT   17   12   15   21                                                  
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0112102
HETATM    1  C1  UNL     1       4.946   2.611  -0.252  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.202   1.607  -1.336  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.611   0.251  -1.044  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.248  -0.244   0.243  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.719  -1.618   0.631  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.266  -1.623   0.844  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.577  -1.394   1.999  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.246  -1.507   1.697  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.166  -1.802   0.366  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.036  -2.030  -0.478  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.502  -0.739  -1.069  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.705  -0.842  -1.937  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.930  -1.377  -1.264  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.384  -0.539  -0.091  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.707   0.851  -0.522  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.156   1.680   0.658  1.00  0.00           C  
HETATM   17  C17 UNL     1      -5.391   1.142   1.334  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.493   1.122   0.343  1.00  0.00           C  
HETATM   19  O1  UNL     1      -6.616   0.216  -0.518  1.00  0.00           O  
HETATM   20  O2  UNL     1      -7.438   2.130   0.345  1.00  0.00           O  
HETATM   21  O3  UNL     1       2.389  -1.861  -0.103  1.00  0.00           O  
HETATM   22  H1  UNL     1       5.312   3.592  -0.616  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.859   2.643  -0.007  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.504   2.398   0.683  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.776   1.997  -2.278  1.00  0.00           H  
HETATM   26  H5  UNL     1       6.310   1.510  -1.458  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.514   0.381  -0.933  1.00  0.00           H  
HETATM   28  H7  UNL     1       4.831  -0.411  -1.894  1.00  0.00           H  
HETATM   29  H8  UNL     1       6.331  -0.302   0.070  1.00  0.00           H  
HETATM   30  H9  UNL     1       4.950   0.448   1.051  1.00  0.00           H  
HETATM   31  H10 UNL     1       5.023  -2.329  -0.157  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.196  -1.852   1.616  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.024  -1.166   2.961  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.413  -1.389   2.373  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.831  -2.457   0.200  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.207  -2.810  -1.192  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.322  -0.317  -1.681  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.681  -0.019  -0.244  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.945   0.165  -2.336  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.503  -1.485  -2.818  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.867  -2.435  -0.979  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.758  -1.314  -2.020  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.661  -0.551   0.747  1.00  0.00           H  
HETATM   44  H23 UNL     1      -4.307  -1.020   0.289  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.790   1.362  -0.917  1.00  0.00           H  
HETATM   46  H25 UNL     1      -4.498   0.820  -1.304  1.00  0.00           H  
HETATM   47  H26 UNL     1      -4.306   2.739   0.367  1.00  0.00           H  
HETATM   48  H27 UNL     1      -3.286   1.682   1.379  1.00  0.00           H  
HETATM   49  H28 UNL     1      -5.221   0.109   1.707  1.00  0.00           H  
HETATM   50  H29 UNL     1      -5.686   1.833   2.150  1.00  0.00           H  
HETATM   51  H30 UNL     1      -8.245   2.143   0.955  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7    7   21
CONECT    7    8   33
CONECT    8    9    9   34
CONECT    9   10   21
CONECT   10   11   35   36
CONECT   11   12   37   38
CONECT   12   13   39   40
CONECT   13   14   41   42
CONECT   14   15   43   44
CONECT   15   16   45   46
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19   19   20
CONECT   20   51
END

HMDB0112102
     RDKit          3D
5-pentyl-2-furannonanoic acid
 51 51  0  0  0  0  0  0  0  0999 V2000
    4.9462    2.6112   -0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2017    1.6073   -1.3356 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6112    0.2507   -1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2481   -0.2439    0.2430 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7189   -1.6180    0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2655   -1.6227    0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5772   -1.3939    1.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2458   -1.5074    1.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1656   -1.8021    0.3656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0356   -2.0297   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5017   -0.7386   -1.0686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7049   -0.8418   -1.9367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9297   -1.3771   -1.2636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3838   -0.5388   -0.0914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7065    0.8507   -0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563    1.6798    0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3906    1.1422    1.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4929    1.1225    0.3434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6156    0.2158   -0.5176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4378    2.1297    0.3446 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3895   -1.8615   -0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3120    3.5920   -0.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8594    2.6431   -0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5038    2.3984    0.6826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7756    1.9973   -2.2777 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3102    1.5099   -1.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5136    0.3806   -0.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311   -0.4107   -1.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3308   -0.3021    0.0700 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9499    0.4484    1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0232   -2.3294   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1956   -1.8520    1.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0236   -1.1663    2.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133   -1.3885    2.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312   -2.4571    0.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2066   -2.8098   -1.1924 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224   -0.3173   -1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6806   -0.0192   -0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9450    0.1646   -2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5032   -1.4855   -2.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8667   -2.4348   -0.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577   -1.3135   -2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6611   -0.5510    0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3069   -1.0199    0.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7900    1.3618   -0.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4978    0.8203   -1.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3061    2.7393    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2863    1.6824    1.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2215    0.1087    1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6864    1.8329    2.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2450    2.1431    0.9548 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  2  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  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  9 21  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 14 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 20 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-(5-Pentylfuran-2-yl)-nonanoate	Generator
9F5	SMPDB, HMDB
9-(5-pentyl-2-furyl)nonanoic acid	SMPDB, HMDB
5-pentyl-2-furannonanoic acid	SMPDB
10,13-epoxy-10,12-octadecadienoic acid	SMPDB, HMDB
10,13-epoxyoctadeca-10,12-dienoic acid	SMPDB, HMDB
9-(5-pentylfuran-2-yl)nonanoic acid	SMPDB, HMDB
9-(5-Pentylfuran-2-yl)nonanoate	Generator, HMDB
5-Pentyl-2-furannonanoate	Generator

Chemical Formula

C₁₈H₃₀O₃

Average Molecular Weight

294.435

Monoisotopic Molecular Weight

294.219494826

IUPAC Name

9-(5-pentylfuran-2-yl)nonanoic acid

Traditional Name

9-(5-pentylfuran-2-yl)nonanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H30O3/c1-2-3-8-11-16-14-15-17(21-16)12-9-6-4-5-7-10-13-18(19)20/h14-15H,2-13H2,1H3,(H,19,20)

InChI Key

BJTONYHCPUUWFX-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	6.09	ALOGPS
logP	5.68	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.83	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	13	ChemAxon
Refractivity	85.59 m³·mol⁻¹	ChemAxon
Polarizability	37.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	174.709	31661259
DarkChem	[M-H]-	173.551	31661259
DeepCCS	[M+H]+	179.938	30932474
DeepCCS	[M-H]-	176.486	30932474
DeepCCS	[M-2H]-	212.312	30932474
DeepCCS	[M+Na]+	188.601	30932474
AllCCS	[M+H]+	179.5	32859911
AllCCS	[M+H-H2O]+	176.4	32859911
AllCCS	[M+NH4]+	182.4	32859911
AllCCS	[M+Na]+	183.3	32859911
AllCCS	[M-H]-	181.8	32859911
AllCCS	[M+Na-2H]-	183.1	32859911
AllCCS	[M+HCOO]-	184.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-pentyl-2-furannonanoic acid	CCCCCC1=CC=C(CCCCCCCCC(O)=O)O1	3413.8	Standard polar	33892256
5-pentyl-2-furannonanoic acid	CCCCCC1=CC=C(CCCCCCCCC(O)=O)O1	2221.0	Standard non polar	33892256
5-pentyl-2-furannonanoic acid	CCCCCC1=CC=C(CCCCCCCCC(O)=O)O1	2221.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-pentyl-2-furannonanoic acid,1TMS,isomer #1	CCCCCC1=CC=C(CCCCCCCCC(=O)O[Si](C)(C)C)O1	2338.4	Semi standard non polar	33892256
5-pentyl-2-furannonanoic acid,1TBDMS,isomer #1	CCCCCC1=CC=C(CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O1	2575.0	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-pentyl-2-furannonanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0fic-9642000000-b13e8b765eb5b8294598	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-pentyl-2-furannonanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8980000000-318307d21f98d5602dba	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-pentyl-2-furannonanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-pentyl-2-furannonanoic 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-pentyl-2-furannonanoic acid 10V, Negative-QTOF	splash10-0006-0090000000-0ca2e152c8c0f191ed16	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 20V, Negative-QTOF	splash10-002g-1290000000-3c4cb9a1a3e3f9bd5eb4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 40V, Negative-QTOF	splash10-0a4m-9620000000-104e833259fd977e918b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 10V, Negative-QTOF	splash10-0006-0090000000-622b0481e999bad50a59	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 20V, Negative-QTOF	splash10-002f-1190000000-1a7338100b3d159a09f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 40V, Negative-QTOF	splash10-0596-7930000000-7a3d82b42088a7be10d0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 10V, Positive-QTOF	splash10-004j-0090000000-4f919ef4dbd6f36b51a0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 20V, Positive-QTOF	splash10-054k-7590000000-5c688f7e60ea1240be8e	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 40V, Positive-QTOF	splash10-0a4u-9310000000-93ec3ab3490de172417c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 10V, Positive-QTOF	splash10-054t-2490000000-a9acb230cb918b9dd280	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 20V, Positive-QTOF	splash10-0a70-8940000000-30d7d47f78f83d332769	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-pentyl-2-furannonanoic acid 40V, Positive-QTOF	splash10-0apl-9300000000-0902754a43825ecb8195	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

53685760

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Vetter W, Wendlinger C (2013). Furan fatty acids – valuable minor fatty acids in food. Lipid Technology.
Wahl HG, Liebich HM, Hoffmann A (1994). Identification of fatty acid methyl esters as minor components of fish oil by multidimensional GC-MSD: New furan fatty acids. Journal of High Resolution Chromatography.
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 5-pentyl-2-furannonanoic acid (HMDB0112102)

MOL for HMDB0112102 (5-pentyl-2-furannonanoic acid)

3D MOL for HMDB0112102 (5-pentyl-2-furannonanoic acid)

3D SDF for HMDB0112102 (5-pentyl-2-furannonanoic acid)

3D-SDF for HMDB0112102 (5-pentyl-2-furannonanoic acid)

PDB for HMDB0112102 (5-pentyl-2-furannonanoic acid)

3D PDB for HMDB0112102 (5-pentyl-2-furannonanoic acid)

SMILES for HMDB0112102 (5-pentyl-2-furannonanoic acid)

INCHI for HMDB0112102 (5-pentyl-2-furannonanoic acid)

Structure for HMDB0112102 (5-pentyl-2-furannonanoic acid)

3D Structure for HMDB0112102 (5-pentyl-2-furannonanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra