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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:31 UTC

Update Date

2022-03-07 02:49:12 UTC

HMDB ID

HMDB0002000

Secondary Accession Numbers

HMDB02000

Metabolite Identification

Common Name

Myristoleic acid

Description

Myristoleic acid, also known as 9-tetradecenoate or myristoleate, 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. Myristoleic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Myristoleic acid exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, myristoleic acid is found in the highest concentration within a few different foods, such as milk (cow), butter, and margarine-like spreads, and in a lower concentration in creams, meat bouillons, and chocolates. Myristoleic acid has also been detected, but not quantified in, several different foods, such as anchovies, loganberries, sunflowers, yellow zucchinis, and dates. This could make myristoleic acid a potential biomarker for the consumption of these foods. Myristoleic acid is a monounsaturated fatty acid that represents approximately 0.3-0.7% of the total fatty acid composition of adipose tissue triacylglycerol in humans (PMID: 10393134 ). It has been suggested that its effective cytotoxic (i.e. cell death inducer) activity could be used for the treatment of prostate cancer (PMID: 11304730 ).

Structure

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

HMDB0002000
     RDKit          3D
Myristoleic acid
 42 41  0  0  0  0  0  0  0  0999 V2000
   -6.3875    0.2247   -0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390    0.0582   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0918    0.7066   -1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6134    0.5284   -0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208   -0.9057   -0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690   -1.5070    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950   -0.8455    1.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1381   -0.9745    1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159   -0.3371    0.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1895   -0.4212    1.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9507    0.2372    0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4395    0.2156    0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001    0.8990   -0.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5829    0.9182   -0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1584    0.4154    0.3188 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3112    1.5170   -1.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8015    1.1779   -0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6132    0.1855   -1.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9413   -0.5827    0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7244    0.6437    0.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6293   -0.9893    0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2727    0.2323   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3453    1.7824   -1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833    1.1171    0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0844    0.9445   -1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -1.5065   -1.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7039   -2.5991    0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864    0.2041    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2379   -1.3787    2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235   -0.4756    2.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1005   -2.0372    2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649    0.7482    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5434   -0.7840   -0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4217   -0.0258    2.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661   -1.5149    1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536   -0.3512   -0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817    1.2641   -0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405    0.6424    1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7575   -0.8657    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6874    1.9315   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8223    0.3334   -1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667    1.1745   -1.8661 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  1  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  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
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 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


  Mrv1652311141917512D          

 16 15  0  0  0  0            999 V2000
 9997.9036 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6184 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3336 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0472 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8742 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5878 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.3036 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.0192 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7328 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1885 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4737 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7589 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.0440 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3290 9998.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.6142 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3290 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  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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>
HMDB0002000

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-

> <INCHI_KEY>
YWWVWXASSLXJHU-WAYWQWQTSA-N

> <FORMULA>
C14H26O2

> <MOLECULAR_WEIGHT>
226.355

> <EXACT_MASS>
226.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.75466002195522

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z)-tetradec-9-enoic acid

> <ALOGPS_LOGP>
5.69

> <JCHEM_LOGP>
5.005523791

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
68.9982

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
myristoleic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002000
     RDKit          3D
Myristoleic acid
 42 41  0  0  0  0  0  0  0  0999 V2000
   -6.3875    0.2247   -0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390    0.0582   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0918    0.7066   -1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6134    0.5284   -0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208   -0.9057   -0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690   -1.5070    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950   -0.8455    1.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1381   -0.9745    1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159   -0.3371    0.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1895   -0.4212    1.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9507    0.2372    0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4395    0.2156    0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001    0.8990   -0.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5829    0.9182   -0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1584    0.4154    0.3188 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3112    1.5170   -1.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8015    1.1779   -0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6132    0.1855   -1.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9413   -0.5827    0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7244    0.6437    0.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6293   -0.9893    0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2727    0.2323   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3453    1.7824   -1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833    1.1171    0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0844    0.9445   -1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -1.5065   -1.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7039   -2.5991    0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864    0.2041    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2379   -1.3787    2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235   -0.4756    2.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1005   -2.0372    2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649    0.7482    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5434   -0.7840   -0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4217   -0.0258    2.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661   -1.5149    1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536   -0.3512   -0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817    1.2641   -0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405    0.6424    1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7575   -0.8657    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6874    1.9315   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8223    0.3334   -1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667    1.1745   -1.8661 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  1  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  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
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 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                                 14-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-NOV-19         0                                  
HETATM    1  C   UNK     0    8662.7538663.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.0888663.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.4238663.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.7558663.832   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.2998663.832   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.6318663.064   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.9678663.832   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8672.3028663.064   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.6348663.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.4198663.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.0848663.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8658.7508663.832   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8657.4158663.064   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8656.0818663.832   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8654.7478663.064   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8656.0818665.373   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    HMDB0002000
HETATM    1  C1  UNL     1      -6.388   0.225  -0.446  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.939   0.058  -0.127  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.092   0.707  -1.209  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.613   0.528  -0.870  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.321  -0.906  -0.797  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.869  -1.507   0.283  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.595  -0.846   1.558  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.138  -0.975   1.978  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.716  -0.337   0.907  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.189  -0.421   1.245  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.951   0.237   0.125  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.440   0.216   0.349  1.00  0.00           C  
HETATM   13  C13 UNL     1       5.100   0.899  -0.830  1.00  0.00           C  
HETATM   14  C14 UNL     1       6.583   0.918  -0.681  1.00  0.00           C  
HETATM   15  O1  UNL     1       7.158   0.415   0.319  1.00  0.00           O  
HETATM   16  O2  UNL     1       7.311   1.517  -1.696  1.00  0.00           O  
HETATM   17  H1  UNL     1      -6.801   1.178  -0.056  1.00  0.00           H  
HETATM   18  H2  UNL     1      -6.613   0.186  -1.526  1.00  0.00           H  
HETATM   19  H3  UNL     1      -6.941  -0.583   0.113  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.724   0.644   0.814  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.629  -0.989   0.046  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.273   0.232  -2.189  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.345   1.782  -1.266  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.383   1.117   0.010  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.084   0.944  -1.785  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.500  -1.506  -1.731  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.704  -2.599   0.153  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.886   0.204   1.570  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.238  -1.379   2.329  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.023  -0.476   2.941  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.101  -2.037   2.057  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.465   0.748   0.813  1.00  0.00           H  
HETATM   33  H17 UNL     1       0.543  -0.784  -0.087  1.00  0.00           H  
HETATM   34  H18 UNL     1       2.422  -0.026   2.233  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.466  -1.515   1.273  1.00  0.00           H  
HETATM   36  H20 UNL     1       2.754  -0.351  -0.800  1.00  0.00           H  
HETATM   37  H21 UNL     1       2.582   1.264  -0.007  1.00  0.00           H  
HETATM   38  H22 UNL     1       4.741   0.642   1.311  1.00  0.00           H  
HETATM   39  H23 UNL     1       4.757  -0.866   0.363  1.00  0.00           H  
HETATM   40  H24 UNL     1       4.687   1.932  -0.905  1.00  0.00           H  
HETATM   41  H25 UNL     1       4.822   0.333  -1.741  1.00  0.00           H  
HETATM   42  H26 UNL     1       8.267   1.174  -1.866  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    6   26
CONECT    6    7   27
CONECT    7    8   28   29
CONECT    8    9   30   31
CONECT    9   10   32   33
CONECT   10   11   34   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

HMDB0002000
     RDKit          3D
Myristoleic acid
 42 41  0  0  0  0  0  0  0  0999 V2000
   -6.3875    0.2247   -0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390    0.0582   -0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0918    0.7066   -1.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6134    0.5284   -0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3208   -0.9057   -0.7975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690   -1.5070    0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5950   -0.8455    1.5584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1381   -0.9745    1.9776 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159   -0.3371    0.9071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1895   -0.4212    1.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9507    0.2372    0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4395    0.2156    0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1001    0.8990   -0.8300 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5829    0.9182   -0.6811 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1584    0.4154    0.3188 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3112    1.5170   -1.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8015    1.1779   -0.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6132    0.1855   -1.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9413   -0.5827    0.1132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7244    0.6437    0.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6293   -0.9893    0.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2727    0.2323   -2.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3453    1.7824   -1.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3833    1.1171    0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0844    0.9445   -1.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -1.5065   -1.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7039   -2.5991    0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8864    0.2041    1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2379   -1.3787    2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235   -0.4756    2.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1005   -2.0372    2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649    0.7482    0.8132 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5434   -0.7840   -0.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4217   -0.0258    2.2327 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4661   -1.5149    1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536   -0.3512   -0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817    1.2641   -0.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7405    0.6424    1.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7575   -0.8657    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6874    1.9315   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8223    0.3334   -1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667    1.1745   -1.8661 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  1  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  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
  6 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 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
(9Z)-Tetradecenoic acid	ChEBI
(Z)-Tetradec-9-enoic acid	ChEBI
9-Tetradecenoic acid	ChEBI
9Z-Tetradecenoic acid	ChEBI
cis-9-Tetradecenoic acid	ChEBI
cis-Delta(9)-Tetradecenoic acid	ChEBI
cis-Tetradec-9-enoic acid	ChEBI
(9Z)-Tetradecenoate	Generator
(Z)-Tetradec-9-enoate	Generator
9-Tetradecenoate	Generator
9Z-Tetradecenoate	Generator
cis-9-Tetradecenoate	Generator
cis-delta(9)-Tetradecenoate	Generator
cis-Δ(9)-tetradecenoate	Generator
cis-Δ(9)-tetradecenoic acid	Generator
cis-Tetradec-9-enoate	Generator
Myristoleate	Generator
(9Z)-Tetradec-9-enoate	HMDB
(9Z)-Tetradec-9-enoic acid	HMDB
(9Z)-9-Tetradecenoic acid	HMDB
(Z)-9-Tetradecenoic acid	HMDB
9(Z)-Tetradecenoic acid	HMDB
9-cis-Tetradecenoic acid	HMDB
FA(14:1(9Z))	HMDB
FA(14:1n5)	HMDB
Myristoleic acid	HMDB
Myristolenic acid	HMDB
Oleomyristic acid	HMDB
cis-delta9-Tetradecenoic acid	HMDB
cis-Δ9-Tetradecenoic acid	HMDB

Chemical Formula

C₁₄H₂₆O₂

Average Molecular Weight

226.355

Monoisotopic Molecular Weight

226.193280076

IUPAC Name

(9Z)-tetradec-9-enoic acid

Traditional Name

myristoleic acid

CAS Registry Number

544-64-9

SMILES

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

InChI Identifier

InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-

InChI Key

YWWVWXASSLXJHU-WAYWQWQTSA-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

long-chain fatty acid (CHEBI:27781 )
tetradecenoic acid (CHEBI:27781 )
Unsaturated fatty acids (C08322 )
Monounsaturated fatty acids (C08322 )
Unsaturated fatty acids (LMFA01030051 )

Ontology

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	338.00 to 339.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.94 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.383 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0022 g/L	ALOGPS
logP	5.69	ALOGPS
logP	5.01	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.99	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	28.75 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]+	162.656	31661259
DarkChem	[M-H]-	160.855	31661259
DeepCCS	[M+H]+	159.652	30932474
DeepCCS	[M-H]-	155.632	30932474
DeepCCS	[M-2H]-	193.082	30932474
DeepCCS	[M+Na]+	168.821	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.	9.61 minutes	32390414
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.	8.5 minutes	32390414
Predicted by Siyang on May 30, 2022	20.048 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.01 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2679.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	553.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	217.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	344.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	516.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	874.9 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	694.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1856.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	563.7 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	1620.1 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	449.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	577.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	535.4 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
Myristoleic acid	CCCC\C=C/CCCCCCCC(O)=O	2679.7	Standard polar	33892256
Myristoleic acid	CCCC\C=C/CCCCCCCC(O)=O	1710.4	Standard non polar	33892256
Myristoleic acid	CCCC\C=C/CCCCCCCC(O)=O	1763.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Myristoleic acid,1TMS,isomer #1	CCCC/C=C\CCCCCCCC(=O)O[Si](C)(C)C	1834.4	Semi standard non polar	33892256
Myristoleic acid,1TBDMS,isomer #1	CCCC/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2070.6	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva

Tissue Locations

Adipose Tissue
Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.016 +/- 0.733 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Myristoleic_acid

METLIN ID

6424

PubChem Compound

5281119

PDB ID

Not Available

ChEBI ID

27781

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1261901

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Mamalakis G, Kafatos A, Board S: Type A behavior and adipose tissue linoleic acid: implications for stress management. J Am Coll Nutr. 1994 Jun;13(3):292-7. [PubMed:8077579 ]
Jiang J, Wolk A, Vessby B: Relation between the intake of milk fat and the occurrence of conjugated linoleic acid in human adipose tissue. Am J Clin Nutr. 1999 Jul;70(1):21-7. [PubMed:10393134 ]
Iguchi K, Okumura N, Usui S, Sajiki H, Hirota K, Hirano K: Myristoleic acid, a cytotoxic component in the extract from Serenoa repens, induces apoptosis and necrosis in human prostatic LNCaP cells. Prostate. 2001 Apr;47(1):59-65. [PubMed:11304730 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Myristoleic acid (HMDB0002000)

MOL for HMDB0002000 (Myristoleic acid)

3D MOL for HMDB0002000 (Myristoleic acid)

3D SDF for HMDB0002000 (Myristoleic acid)

3D-SDF for HMDB0002000 (Myristoleic acid)

PDB for HMDB0002000 (Myristoleic acid)

3D PDB for HMDB0002000 (Myristoleic acid)

SMILES for HMDB0002000 (Myristoleic acid)

INCHI for HMDB0002000 (Myristoleic acid)

Structure for HMDB0002000 (Myristoleic acid)

3D Structure for HMDB0002000 (Myristoleic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized