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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:03 UTC

HMDB ID

HMDB0000499

Secondary Accession Numbers

HMDB00499

Metabolite Identification

Common Name

5-Tetradecenoic acid

Description

5-Tetradecenoic acid (CAS: 544-66-1), also known as physeterate or physeteric acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, 5-tetradecenoic acid is considered to be a fatty acid lipid molecule. 5-Tetradecenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 5-Tetradecenoic acid can be found primarily in blood. Within the cell, 5-tetradecenoic acid is primarily located in the cytoplasm and in the membrane. It can also be found in the extracellular space. 5-Tetradecenoic acid is an intermediate of unsaturated fatty acid metabolism found in the plasma of patients with very long chain acyl-CoA dehydrogenase (VLCAD) deficiency, a genetic disorder (PMID: 7586519 ).

Structure

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

HMDB0000499
     RDKit          3D
5-Tetradecenoic acid
 42 41  0  0  0  0  0  0  0  0999 V2000
   -5.8890   -0.0167   -2.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8180    0.2477   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6603   -1.0359   -0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6311   -0.9331    0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532   -0.5912    0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -0.5162    1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0987   -0.1840    1.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1600    1.1369    0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5192    1.5573    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6101    0.8732    0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    1.4091   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5919    0.5143   -1.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8958   -0.8621   -0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8036   -0.8938    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1007   -1.9848    0.9513 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3422    0.2626    0.9495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8897    0.1260   -1.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8133    0.6965   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8446   -1.0528   -2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1258    1.0913   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113    0.5311   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6430   -1.2062    0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5077   -1.8839   -0.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -1.9287    1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9693   -0.2164    1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551    0.3362   -0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145   -1.3868   -0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3378   -1.5237    1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7364    0.1885    2.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4535   -0.9808    0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7012   -0.2538    2.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485    1.0759   -0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488    1.9321    1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6035    2.5221   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809   -0.0708    0.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5257    1.6569    0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    2.3914   -0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5710    1.0152   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0267    0.5171   -2.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623   -1.3671   -1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932   -1.4930   -0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1570    0.3005    1.5321 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 16 42  1  0
M  END


  Mrv1652303192021432D          

 16 15  0  0  0  0            999 V2000
 9997.9490 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6639 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3795 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0931 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8088 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5224 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2381 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9537 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6673 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2342 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5192 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8044 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0895 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3747 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6597 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3747 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000499

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC\C=C\CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9+

> <INCHI_KEY>
AFGUVBVUFZMJMX-MDZDMXLPSA-N

> <FORMULA>
C14H26O2

> <MOLECULAR_WEIGHT>
226.355

> <EXACT_MASS>
226.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.144877503130864

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-tetradec-5-enoic acid

> <ALOGPS_LOGP>
5.77

> <JCHEM_LOGP>
5.005523791

> <ALOGPS_LOGS>
-5.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885676019177561

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
68.9982

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
physeteric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000499
     RDKit          3D
5-Tetradecenoic acid
 42 41  0  0  0  0  0  0  0  0999 V2000
   -5.8890   -0.0167   -2.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8180    0.2477   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6603   -1.0359   -0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6311   -0.9331    0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532   -0.5912    0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -0.5162    1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0987   -0.1840    1.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1600    1.1369    0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5192    1.5573    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6101    0.8732    0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    1.4091   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5919    0.5143   -1.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8958   -0.8621   -0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8036   -0.8938    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1007   -1.9848    0.9513 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3422    0.2626    0.9495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8897    0.1260   -1.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8133    0.6965   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8446   -1.0528   -2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1258    1.0913   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113    0.5311   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6430   -1.2062    0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5077   -1.8839   -0.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -1.9287    1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9693   -0.2164    1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551    0.3362   -0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145   -1.3868   -0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3378   -1.5237    1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7364    0.1885    2.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4535   -0.9808    0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7012   -0.2538    2.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485    1.0759   -0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488    1.9321    1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6035    2.5221   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809   -0.0708    0.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5257    1.6569    0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    2.3914   -0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5710    1.0152   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0267    0.5171   -2.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623   -1.3671   -1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932   -1.4930   -0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1570    0.3005    1.5321 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 16 42  1  0
M  END

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0    8662.8388663.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.1738663.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.5088663.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.8408663.832   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.1768663.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.5088663.832   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.8448663.064   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8672.1808663.832   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.5128663.064   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.5048663.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.1698663.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8658.8358663.832   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8657.5008663.064   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8656.1668663.832   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8654.8318663.064   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8656.1668665.373   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0000499
HETATM    1  C1  UNL     1      -5.889  -0.017  -2.057  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.818   0.248  -0.997  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.660  -1.036  -0.216  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.631  -0.933   0.874  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.253  -0.591   0.322  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.317  -0.516   1.485  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.099  -0.184   1.120  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.160   1.137   0.444  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.519   1.557   0.043  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.610   0.873   0.238  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.917   1.409  -0.214  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.592   0.514  -1.211  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.896  -0.862  -0.739  1.00  0.00           C  
HETATM   14  C14 UNL     1       5.804  -0.894   0.423  1.00  0.00           C  
HETATM   15  O1  UNL     1       6.101  -1.985   0.951  1.00  0.00           O  
HETATM   16  O2  UNL     1       6.342   0.263   0.949  1.00  0.00           O  
HETATM   17  H1  UNL     1      -6.890   0.126  -1.578  1.00  0.00           H  
HETATM   18  H2  UNL     1      -5.813   0.697  -2.894  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.845  -1.053  -2.433  1.00  0.00           H  
HETATM   20  H4  UNL     1      -5.126   1.091  -0.376  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.911   0.531  -1.549  1.00  0.00           H  
HETATM   22  H6  UNL     1      -5.643  -1.206   0.300  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.508  -1.884  -0.884  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.544  -1.929   1.343  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.969  -0.216   1.620  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.355   0.336  -0.246  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.915  -1.387  -0.372  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.338  -1.524   1.983  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.736   0.189   2.245  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.454  -0.981   0.427  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.701  -0.254   2.043  1.00  0.00           H  
HETATM   32  H16 UNL     1      -0.448   1.076  -0.484  1.00  0.00           H  
HETATM   33  H17 UNL     1      -0.249   1.932   1.114  1.00  0.00           H  
HETATM   34  H18 UNL     1       1.603   2.522  -0.456  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.581  -0.071   0.719  1.00  0.00           H  
HETATM   36  H20 UNL     1       4.526   1.657   0.671  1.00  0.00           H  
HETATM   37  H21 UNL     1       3.744   2.391  -0.720  1.00  0.00           H  
HETATM   38  H22 UNL     1       5.571   1.015  -1.465  1.00  0.00           H  
HETATM   39  H23 UNL     1       4.027   0.517  -2.163  1.00  0.00           H  
HETATM   40  H24 UNL     1       5.462  -1.367  -1.576  1.00  0.00           H  
HETATM   41  H25 UNL     1       3.993  -1.493  -0.594  1.00  0.00           H  
HETATM   42  H26 UNL     1       7.157   0.301   1.532  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   10   34
CONECT   10   11   35
CONECT   11   12   36   37
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   15   16
CONECT   16   42
END

HMDB0000499
     RDKit          3D
5-Tetradecenoic acid
 42 41  0  0  0  0  0  0  0  0999 V2000
   -5.8890   -0.0167   -2.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8180    0.2477   -0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6603   -1.0359   -0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6311   -0.9331    0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532   -0.5912    0.3216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -0.5162    1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0987   -0.1840    1.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1600    1.1369    0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5192    1.5573    0.0432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6101    0.8732    0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    1.4091   -0.2140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5919    0.5143   -1.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8958   -0.8621   -0.7385 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8036   -0.8938    0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1007   -1.9848    0.9513 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3422    0.2626    0.9495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8897    0.1260   -1.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8133    0.6965   -2.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8446   -1.0528   -2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1258    1.0913   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113    0.5311   -1.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6430   -1.2062    0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5077   -1.8839   -0.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5444   -1.9287    1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9693   -0.2164    1.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3551    0.3362   -0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145   -1.3868   -0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3378   -1.5237    1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7364    0.1885    2.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4535   -0.9808    0.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7012   -0.2538    2.0433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4485    1.0759   -0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488    1.9321    1.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6035    2.5221   -0.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5809   -0.0708    0.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5257    1.6569    0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    2.3914   -0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5710    1.0152   -1.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0267    0.5171   -2.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4623   -1.3671   -1.5763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9932   -1.4930   -0.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1570    0.3005    1.5321 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  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Tetradecenoate	Generator
Physeterate	HMDB
Physeteric acid	HMDB
Physoterate	HMDB
Physoteric acid	HMDB
(5E)-5-Tetradecenoic acid	HMDB
(e)-5-Tetradecenoic acid	HMDB
C14:1W9	HMDB
FA(14:1(5E))	HMDB
FA(14:1n9)	HMDB
trans-5-Tetradecenoic acid	HMDB
5-Tetradecenoic acid	HMDB

Chemical Formula

C₁₄H₂₆O₂

Average Molecular Weight

226.355

Monoisotopic Molecular Weight

226.193280076

IUPAC Name

(5E)-tetradec-5-enoic acid

Traditional Name

physeteric acid

CAS Registry Number

5684-69-5

SMILES

CCCCCCCC\C=C\CCCC(O)=O

InChI Identifier

InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h9-10H,2-8,11-13H2,1H3,(H,15,16)/b10-9+

InChI Key

AFGUVBVUFZMJMX-MDZDMXLPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Unsaturated fatty acids (LMFA01030913 )

Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Very Long Chain Acyl-CoA Dehydrogenase Deficiency (HMDB: HMDB0000499)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7586519)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0000499)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000499)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000499)

Source

Endogenous

Endogenous (HMDB: HMDB0000499)

Animal

Animal (HMDB: HMDB0000499)

Exogenous

Food

Food (HMDB: HMDB0000499)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Exogenous (HMDB: HMDB0000499)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000499)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000499)

Lipid metabolism pathway (HMDB: HMDB0000499)

Cellular process

Cell signaling (HMDB: HMDB0000499)

Biochemical process

Lipid transport (HMDB: HMDB0000499)

Role

Biological role

Energy source (HMDB: HMDB0000499)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000499)

Physical Properties

State

Solid

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
Water Solubility	0.0018 g/L	ALOGPS
logP	5.77	ALOGPS
logP	5.01	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	69 m³·mol⁻¹	ChemAxon
Polarizability	29.14 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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]+	160.471	31661259
DarkChem	[M-H]-	160.829	31661259
AllCCS	[M+H]+	160.704	32859911
AllCCS	[M-H]-	163.089	32859911
DeepCCS	[M+H]+	158.606	30932474
DeepCCS	[M-H]-	154.584	30932474
DeepCCS	[M-2H]-	192.155	30932474
DeepCCS	[M+Na]+	167.819	30932474
AllCCS	[M+H]+	160.7	32859911
AllCCS	[M+H-H2O]+	157.3	32859911
AllCCS	[M+NH4]+	163.9	32859911
AllCCS	[M+Na]+	164.8	32859911
AllCCS	[M-H]-	163.1	32859911
AllCCS	[M+Na-2H]-	164.4	32859911
AllCCS	[M+HCOO]-	165.9	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. Predicted by Afia on May 17, 2022.	9.6 minutes	32390414
Predicted by Siyang on May 30, 2022	20.0259 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.13 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2681.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	550.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	218.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	344.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	512.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	872.7 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	697.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1849.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	562.1 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	1607.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	671.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	448.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	569.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	526.2 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Tetradecenoic acid	CCCCCCCC\C=C\CCCC(O)=O	2690.8	Standard polar	33892256
5-Tetradecenoic acid	CCCCCCCC\C=C\CCCC(O)=O	1704.8	Standard non polar	33892256
5-Tetradecenoic acid	CCCCCCCC\C=C\CCCC(O)=O	1758.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Tetradecenoic acid,1TMS,isomer #1	CCCCCCCC/C=C/CCCC(=O)O[Si](C)(C)C	1827.8	Semi standard non polar	33892256
5-Tetradecenoic acid,1TBDMS,isomer #1	CCCCCCCC/C=C/CCCC(=O)O[Si](C)(C)C(C)(C)C	2062.4	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-Tetradecenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9500000000-0b0af7482ba8816cc6ab	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Tetradecenoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0g7r-9320000000-cb804ee15a90c6b4b818	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Tetradecenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Tetradecenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Tetradecenoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	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-Tetradecenoic acid 10V, Positive-QTOF	splash10-0a4i-0290000000-7a4f23ca69ff41d25e22	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Tetradecenoic acid 20V, Positive-QTOF	splash10-0a7i-5930000000-871f7b73a233ffe1c48f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Tetradecenoic acid 40V, Positive-QTOF	splash10-052f-9500000000-b88980b220617e7a4981	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Tetradecenoic acid 10V, Negative-QTOF	splash10-004i-0190000000-7f930e0e03b1fa3a9fd4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Tetradecenoic acid 20V, Negative-QTOF	splash10-057i-1390000000-353787f26fcfb5c6dd0b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Tetradecenoic acid 40V, Negative-QTOF	splash10-0a4l-9400000000-53c75124447efe309e95	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Tetradecenoic acid 10V, Negative-QTOF	splash10-004i-0090000000-6c6d923a7644bf907b73	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Tetradecenoic acid 20V, Negative-QTOF	splash10-056r-1090000000-f0aa2436f161b1da4f07	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Tetradecenoic acid 40V, Negative-QTOF	splash10-052f-9400000000-355a8cd627eeee3a751c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Tetradecenoic acid 10V, Positive-QTOF	splash10-0a7i-9430000000-1fba7cb19884c7c32cd4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Tetradecenoic acid 20V, Positive-QTOF	splash10-0apj-9100000000-bb1fd580717537a9dc0c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Tetradecenoic acid 40V, Positive-QTOF	splash10-05mo-9000000000-cb2869d738fb7b21f4a0	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.5 (0.6 - 2.3) uM	Adult (>18 years old)	Both	Normal	7586519	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	50.0 (14.3 - 84.0) uM	Adult (>18 years old)	Not Specified	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	7586519	details

Associated Disorders and Diseases

Disease References

Very Long Chain Acyl-CoA Dehydrogenase Deficiency
Onkenhout W, Venizelos V, van der Poel PF, van den Heuvel MP, Poorthuis BJ: Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin Chem. 1995 Oct;41(10):1467-74. [PubMed:7586519 ]

Associated OMIM IDs

201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022089

KNApSAcK ID

Not Available

Chemspider ID

4445867

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5485

PubChem Compound

5282740

PDB ID

Not Available

ChEBI ID

89393

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Toyama, Yoshiyuki; Tsuchiya, Tomotaro. The separation of physeteric acid from sardine and pilot-whale oils. Kogyo Kagaku Zasshi (1935), 38 Suppl. binding 680-4.

Material Safety Data Sheet (MSDS)

Not Available

General References

Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
Onkenhout W, Venizelos V, van der Poel PF, van den Heuvel MP, Poorthuis BJ: Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin Chem. 1995 Oct;41(10):1467-74. [PubMed:7586519 ]
Onkenhout W, Venizelos V, Scholte HR, De Klerk JB, Poorthuis BJ: Intermediates of unsaturated fatty acid oxidation are incorporated in triglycerides but not in phospholipids in tissues from patients with mitochondrial beta-oxidation defects. J Inherit Metab Dis. 2001 Jun;24(3):337-44. [PubMed:11486898 ]

Showing metabocard for 5-Tetradecenoic acid (HMDB0000499)

MOL for HMDB0000499 (5-Tetradecenoic acid)

3D MOL for HMDB0000499 (5-Tetradecenoic acid)

3D SDF for HMDB0000499 (5-Tetradecenoic acid)

3D-SDF for HMDB0000499 (5-Tetradecenoic acid)

PDB for HMDB0000499 (5-Tetradecenoic acid)

3D PDB for HMDB0000499 (5-Tetradecenoic acid)

SMILES for HMDB0000499 (5-Tetradecenoic acid)

INCHI for HMDB0000499 (5-Tetradecenoic acid)

Structure for HMDB0000499 (5-Tetradecenoic acid)

3D Structure for HMDB0000499 (5-Tetradecenoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra