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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

Adipose tissue (HMDB: HMDB0002000)
Adipose tissue (HMDB: HMDB0002000)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Saliva (HMDB: HMDB0002000)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0002000)

Organ

Placenta (HMDB: HMDB0002000)

Excreta

Biofluid or Excreta

Feces (PMID: 22411374)
Urine (HMDB: HMDB0002000)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002000)

Source

Endogenous

Endogenous (HMDB: HMDB0002000)

Plant

Animal

Animal (HMDB: HMDB0002000)

Exogenous

Food

Food (HMDB: HMDB0002000)

Herb and spice

Herb

Spice

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Anchovy (FooDB: FOOD00566)
Blue whiting (FooDB: FOOD00567)
Carp bream (FooDB: FOOD00568)
Clupeinae (Herring, Sardine, Sprat) (FooDB: FOOD00520)
Burbot (FooDB: FOOD00313)
Sturgeon (FooDB: FOOD00570)
Charr (FooDB: FOOD00571)
Gadus (Common cod) (FooDB: FOOD00515)
Common dab (FooDB: FOOD00574)
Spiny dogfish (FooDB: FOOD00575)
Anguilliformes (FooDB: FOOD00577)
Flatfish (FooDB: FOOD00535)
Garfish (FooDB: FOOD00579)
Haddock (FooDB: FOOD00374)
Gadiformes (FooDB: FOOD00580)
Atlantic halibut (FooDB: FOOD00516)
Greenland halibut/turbot (FooDB: FOOD00370)
Lake trout (FooDB: FOOD00582)
Lemon sole (FooDB: FOOD00583)
Common ling (FooDB: FOOD00397)
Lumpsucker (FooDB: FOOD00585)
Scombridae (Bonito, Mackerel, Tuna) (FooDB: FOOD00586)
Norway haddock (FooDB: FOOD00588)
Norway pout (FooDB: FOOD00590)
Perciformes (FooDB: FOOD00527)
Northern pike (FooDB: FOOD00431)
Pikeperch (FooDB: FOOD00595)
Pleuronectidae (Dab, Halibut, Plaice) (FooDB: FOOD00596)
Pollock (FooDB: FOOD00513)
Rainbow trout (FooDB: FOOD00444)
Pacific ocean perch (FooDB: FOOD00598)
Salmonidae (Salmon, Trout) (FooDB: FOOD00493)
True sole (FooDB: FOOD00604)
Catfish (FooDB: FOOD00605)
Thunnus (FooDB: FOOD00607)
Turbot (FooDB: FOOD00364)
Whitefish (FooDB: FOOD00503)
Whiting (FooDB: FOOD00504)
Atlantic wolffish (FooDB: FOOD00296)

Crustacean

Fish product

Other fish product (FooDB: FOOD00665)

Amphibian

True frog (FooDB: FOOD00578)

Mollusk

Pinniped

True seal (FooDB: FOOD00600)

Seaweed

Red algae (FooDB: FOOD00601)
Kombu (FooDB: FOOD00602)
Agar (FooDB: FOOD00284)

Cetacean

Cetacea (Dolphin, Porpoise, Whale) (FooDB: FOOD00609)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)

Fruit product

Other fruit product (FooDB: FOOD00765)
Fruit preserve (FooDB: FOOD00660)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Beverage

Distilled beverage

Spirit (FooDB: FOOD00276)
Gin (FooDB: FOOD00625)
Liquor (FooDB: FOOD00616)
Rum (FooDB: FOOD00629)
Vodka (FooDB: FOOD00622)
Whisky (FooDB: FOOD00623)

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Other beverage

Fortified wines

Water

Water (FooDB: FOOD00664)

Alcoholic beverage

Other alcoholic beverage (FooDB: FOOD00278)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)

Other vegetable

Okra (FooDB: FOOD00420)

Stalk vegetable

Garden rhubarb (FooDB: FOOD00154)

Baby food

Baby food (FooDB: FOOD00668)

Animal origin

Swine

Domestic pig (FooDB: FOOD00536)

Bovine

Cattle (Beef, Veal) (FooDB: FOOD00495)

Poultry

Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Turkey (FooDB: FOOD00494)
Chicken (FooDB: FOOD00329)

Lagomorph

Mountain hare (FooDB: FOOD00581)
Rabbit (FooDB: FOOD00528)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Leavened bread

Wheat bread (FooDB: FOOD00808)
Rye bread (FooDB: FOOD00809)

Cereal

Barley (FooDB: FOOD00088)
Common buckwheat (FooDB: FOOD00079)
Corn (FooDB: FOOD00205)
Millet (FooDB: FOOD00126)
Oat (FooDB: FOOD00022)
Rice (FooDB: FOOD00125)
Rye (FooDB: FOOD00169)
Wheat (FooDB: FOOD00561)
Hard wheat (FooDB: FOOD00242)
White bread (FooDB: FOOD00987)

Cereal product

Bread products

Other bread product (FooDB: FOOD00805)

Flat bread

Crisp bread (FooDB: FOOD00640)

Baking good

Sugar

Sugar (FooDB: FOOD00651)

Dressing

Salad dressing (FooDB: FOOD00645)

Condiment

Substitute

Sugar substitute (FooDB: FOOD00656)

Seasoning

Salt (FooDB: FOOD00647)
Vinegar (FooDB: FOOD00628)

Sauce

Sauce (FooDB: FOOD00646)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Chickpea (FooDB: FOOD00047)
Common pea (FooDB: FOOD00141)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Miso (FooDB: FOOD00695)
Soy milk (FooDB: FOOD00736)
Soy sauce (FooDB: FOOD00694)
Tofu (FooDB: FOOD00696)

Unclassified food or beverage

Unclassified food or beverage (FooDB: FOOD00672)

Dish

Ground meat

Sausage (FooDB: FOOD00652)
Meatball (FooDB: FOOD00653)
Pate (FooDB: FOOD00655)
Cold cut (FooDB: FOOD00770)

Other dish

Dumpling (FooDB: FOOD00669)
Other dish (FooDB: FOOD00836)
Pizza (FooDB: FOOD00637)
Soup (FooDB: FOOD00670)

Fat and oil

Vegetable fat

Margarine-like spread (FooDB: FOOD00844)
Margarine (FooDB: FOOD00843)

Animal fat

Fish oil (FooDB: FOOD00990)
Fats and oils (FooDB: FOOD00864)

Milk and milk product

Other milk product

Butter (FooDB: FOOD00648)
Casein (FooDB: FOOD00659)
Whey (FooDB: FOOD00658)
Cream (FooDB: FOOD00650)
Dried milk (FooDB: FOOD00689)

Fermented milk product

Cheese (FooDB: FOOD00617)
Yogurt (FooDB: FOOD00620)
Ymer (FooDB: FOOD00638)

Unfermented milk

Fermented milk

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)

Confectionery

Candy

Dessert

Pastry (FooDB: FOOD00641)
Gelatin dessert (FooDB: FOOD00725)

Other confectionery

Honey (FooDB: FOOD00626)
Marzipan (FooDB: FOOD00644)
Toffee (FooDB: FOOD00635)
Meringue (FooDB: FOOD00680)

Frozen dessert

Ice cream (FooDB: FOOD00624)
Other frozen dessert (FooDB: FOOD00729)

Spread

Chocolate spread (FooDB: FOOD00676)

Cocoa and cocoa product

Cocoa product

Coffee and coffee product

Coffee

Snack

Cracker (FooDB: FOOD00787)
Other snack food (FooDB: FOOD00639)

Egg

Eggs (FooDB: FOOD00619)

Tea

Exogenous (HMDB: HMDB0002000)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002000)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002000)

Lipid metabolism pathway (HMDB: HMDB0002000)

Cellular process

Cell signaling (HMDB: HMDB0002000)

Biochemical process

Lipid transport (HMDB: HMDB0002000)

Role

Industrial application

Manufacturing industry

Material processing agent

Solid material processing agent

Protective agent

Antioxidant (HMDB: HMDB0002000)
Antioxidant (HMDB: HMDB0002000)

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002000)

Biological role

Energy source (HMDB: HMDB0002000)

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 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

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Myristoleic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9800000000-71fb52f9fefd5cb3790e	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Myristoleic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00a9-9520000000-b85c6ba98a1ce24c3518	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Myristoleic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0aou-9100000000-1823acbf402fe87fba5b	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristoleic acid LC-ESI-QQ , negative-QTOF	splash10-004i-0090000000-57b079c6d11a9714cb51	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristoleic acid LC-ESI-QQ , negative-QTOF	splash10-004i-0090000000-4fcda40660e1f5947eb6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristoleic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-9120000000-50121015a2477be41bec	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristoleic acid LC-ESI-QQ , negative-QTOF	splash10-0595-9000000000-98c3d58fb9e1e7c41c90	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristoleic acid LC-ESI-IT , negative-QTOF	splash10-004i-0090000000-e588f40ae851251aee81	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 10V, Positive-QTOF	splash10-056r-0390000000-6a2bf4ff780562d5fdd9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 20V, Positive-QTOF	splash10-00lr-6930000000-bd53c7ac25c8930728e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 40V, Positive-QTOF	splash10-052f-9300000000-cd017bd3efd7fa06ee6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 10V, Negative-QTOF	splash10-004i-0190000000-c6a068748e37ad83d1d8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 20V, Negative-QTOF	splash10-0059-1590000000-999dd13c5871dbb32a3f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 40V, Negative-QTOF	splash10-0a4i-9400000000-97121a85c8e202172ecf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 10V, Negative-QTOF	splash10-004i-0090000000-6c6d923a7644bf907b73	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 20V, Negative-QTOF	splash10-056r-1090000000-bf30a380076470239567	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 40V, Negative-QTOF	splash10-0006-9300000000-b037435cdbd96f2e828d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 10V, Positive-QTOF	splash10-0a7j-9330000000-790a04dc9533b3b6607b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 20V, Positive-QTOF	splash10-05o1-9000000000-fa6bdbb819001b908171	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristoleic acid 40V, Positive-QTOF	splash10-0aou-9000000000-aaba2dc5fc19c49556c2	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum

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	Adult (>18 years old)	Both	Normal	29808030	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	Infant (0-1 year old)	Both	Normal	22411374	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 Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra