MiMeDB: Showing metabocard for Myristoleic acid (MMDBc0000580)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:50:23 UTC

Update Date

2024-09-29 09:03:42 UTC

Metabolite ID

MMDBc0000580

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>
MMDBc0000580

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₄H₂₆O₂

Average Mass

226.355

Monoisotopic Mass

226.193280076

IUPAC Name

(9Z)-tetradec-9-enoic acid

Traditional Name

myristoleic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9800000000-71fb52f9fefd5cb3790e	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00a9-9520000000-b85c6ba98a1ce24c3518	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0090000000-57b079c6d11a9714cb51	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0090000000-4fcda40660e1f5947eb6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9120000000-50121015a2477be41bec	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0595-9000000000-98c3d58fb9e1e7c41c90	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-004i-0090000000-e588f40ae851251aee81	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0390000000-6a2bf4ff780562d5fdd9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-6930000000-bd53c7ac25c8930728e7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9300000000-cd017bd3efd7fa06ee6e	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0190000000-c6a068748e37ad83d1d8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0059-1590000000-999dd13c5871dbb32a3f	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9400000000-97121a85c8e202172ecf	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-6c6d923a7644bf907b73	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-1090000000-bf30a380076470239567	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9300000000-b037435cdbd96f2e828d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a7j-9330000000-790a04dc9533b3b6607b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05o1-9000000000-fa6bdbb819001b908171	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aou-9000000000-aaba2dc5fc19c49556c2	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0aou-9100000000-1823acbf402fe87fba5b	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Blood
Feces
Placenta

Tissue Locations

Adipose Tissue
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0007080	1-Tetradec-7-enoyl-sn-glycerol 3-phosphate	Glycerol 3-phosphate	Not Available	VMH	30371894
MMDBr0007087	1-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1)	sn-glycero-3-phosphoethanolamine	Not Available	VMH	30371894
MMDBr0007094	1-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1)	Glycerophosphoglycerol	Not Available	VMH	30371894
MMDBr0007101	2-tetradec-7-enoyl-sn-glycerol 3-phosphate	Glycerol 3-phosphate	Not Available	VMH	30371894
MMDBr0007108	2-Acyl-sn-glycero-3-phosphoethanolamine (N-C14:1)	sn-glycero-3-phosphoethanolamine	Not Available	VMH	30371894
MMDBr0007114	2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1)	Glycerophosphoglycerol	Not Available	VMH	30371894
MMDBr0009177	Myristoleic acid	9E-Tetradecenoyl Coenzyme A	Not Available	VMH	30371894
MMDBr0009178	9E-Tetradecenoyl Coenzyme A	Myristoleic acid	acyl-CoA thioesterase 1	VMH	30371894
MMDBr0009967	Myristoleic acid	9E-Tetradecenoyl Coenzyme A	Not Available	VMH	30371894
MMDBr0010203	Cholest-5-En-3B-Yl (9Z-Tetradecenoate)	Cholesterol	carboxyl ester lipase	VMH; KEGG	30371894
MMDBr0010242	Cholest-5-En-3B-Yl (9Z-Tetradecenoate)	Cholesterol	carboxyl ester lipase	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	23	Human ; Human urine; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Firmicutes	285	Human feces; Human pleural fluid plaque; Human ; Human urine; Human mucosa; Human sputum; Human saliva; Human supragingival plaque; Human stool; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Proteobacteria	152	Human feces; Human sputum; Human ; Human unknown; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	117	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	5	Human feces; Human	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference
Plant	Seed	Petroselinum crispum	FooDB	31437929

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	2.016	0.733	uM	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human Blood	Detected and Quantified	2.016	0.733	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Adipose tissue	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Infant (0-1 year old)	Both	Normal	HMDB	22411374
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0002000

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

References

Synthesis Reference

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. doi: 10.1080/07315724.1994.10718411. [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. doi: 10.1093/ajcn/70.1.21. [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. doi: 10.1002/pros.1047. [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 (MMDBc0000580)

MOL for #<Metabolite:0x00007f46f8080340>

3D MOL for #<Metabolite:0x00007f46f8080340>

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3D-SDF for #<Metabolite:0x00007f46f8080340>

PDB for #<Metabolite:0x00007f46f8080340>

3D PDB for #<Metabolite:0x00007f46f8080340>

SMILES for #<Metabolite:0x00007f46f8080340>

INCHI for #<Metabolite:0x00007f46f8080340>

Structure for #<Metabolite:0x00007f46f8080340>

3D Structure for #<Metabolite:0x00007f46f8080340>