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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (67)transporters (1) Show 68 proteins XML

enzymes (67)transporters (1) Show 68 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:06 UTC

HMDB ID

HMDB0000806

Secondary Accession Numbers

HMDB00806

Metabolite Identification

Common Name

Myristic acid

Description

Myristic acid, also known as tetradecanoic acid or C14:0, 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. Myristic acid (its ester is called myristate) is a saturated fatty acid that has 14 carbons; as such, it is a very hydrophobic molecule that is practically insoluble in water. It exists as an oily white crystalline solid. Myristic acid is found in all living organisms ranging from bacteria to plants to animals, and is found in most animal and vegetable fats, particularly butterfat, as well as coconut, palm, and nutmeg oils. Industrially, myristic acid is used to synthesize a variety of flavour compounds and as an ingredient in soaps and cosmetics (Dorland, 28th ed). Within eukaryotic cells, myristic acid is also commonly conjugated to a penultimate N-terminal glycine residue in receptor-associated kinases to confer membrane localization of these enzymes (a post-translational modification called myristoylation via the enzyme N-myristoyltransferase). Myristic acid has a high enough hydrophobicity to allow the myristoylated protein to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of eukaryotic cells. Also, this fatty acid is known because it accumulates as fat in the body; however, its consumption also impacts positively on cardiovascular health (see, for example, PMID: 15936650 ). Myristic acid is named after the scientific name for nutmeg, Myristica fragrans, from which it was first isolated in 1841 by Lyon Playfair.

Structure

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

HMDB0000806
     RDKit          3D
Myristic acid
 44 43  0  0  0  0  0  0  0  0999 V2000
    5.6666   -0.1656   -2.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8305    0.7014   -0.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443    0.0119    0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6644   -0.1516    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9495   -0.8292    1.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5078   -1.0109    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8600    0.3072    0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6310    0.1727    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111   -0.4743    1.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8704   -0.5884    0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4855    0.7516    0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9304    0.6982    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1195   -0.1117   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5625   -0.1672   -1.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3814    0.4303   -0.5425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9616   -0.8589   -2.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6020   -0.1777   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8198    0.2055   -2.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4148   -1.2037   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9081    0.8318   -0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980    1.7034   -0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6146   -0.9694    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.6173    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6177   -0.7061   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2630    0.8705   -0.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545   -1.7974    1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963   -0.1940    2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -1.5784   -0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -1.6401    1.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0241    1.0434    1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    0.7873   -0.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9771    1.2477    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6861   -0.3296   -0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0442   -1.4776    1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673    0.2137    2.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9571   -1.2785    0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4463   -1.0870    1.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9696    1.2609   -0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3940    1.3370    1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5801    0.3386    1.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2300    1.7519    0.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5827    0.4198   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7272   -1.1471   -0.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4599   -0.4390   -3.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  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
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  0
M  END


  Mrv1652309272007352D          

 16 15  0  0  0  0            999 V2000
   -3.9296   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6440   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3585   -1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6440   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  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
  1 14  1  0  0  0  0
 14 16  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000806

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)

> <INCHI_KEY>
TUNFSRHWOTWDNC-UHFFFAOYSA-N

> <FORMULA>
C14H28O2

> <MOLECULAR_WEIGHT>
228.3709

> <EXACT_MASS>
228.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
30.096995398489902

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
tetradecanoic acid

> <ALOGPS_LOGP>
6.10

> <JCHEM_LOGP>
5.367445447666666

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019655228562

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
67.88159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
myristic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000806
     RDKit          3D
Myristic acid
 44 43  0  0  0  0  0  0  0  0999 V2000
    5.6666   -0.1656   -2.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8305    0.7014   -0.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443    0.0119    0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6644   -0.1516    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9495   -0.8292    1.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5078   -1.0109    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8600    0.3072    0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6310    0.1727    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111   -0.4743    1.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8704   -0.5884    0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4855    0.7516    0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9304    0.6982    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1195   -0.1117   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5625   -0.1672   -1.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3814    0.4303   -0.5425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9616   -0.8589   -2.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6020   -0.1777   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8198    0.2055   -2.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4148   -1.2037   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9081    0.8318   -0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980    1.7034   -0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6146   -0.9694    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.6173    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6177   -0.7061   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2630    0.8705   -0.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545   -1.7974    1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963   -0.1940    2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -1.5784   -0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -1.6401    1.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0241    1.0434    1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    0.7873   -0.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9771    1.2477    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6861   -0.3296   -0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0442   -1.4776    1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673    0.2137    2.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9571   -1.2785    0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4463   -1.0870    1.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9696    1.2609   -0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3940    1.3370    1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5801    0.3386    1.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2300    1.7519    0.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5827    0.4198   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7272   -1.1471   -0.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4599   -0.4390   -3.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  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
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -7.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.002  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.668  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.334  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.335  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.669  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.669  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -10.003  -3.080   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -8.669  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2   14                                                       
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   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14    1   16   15                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0000806
HETATM    1  C1  UNL     1       5.667  -0.166  -2.001  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.830   0.701  -0.774  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.144   0.012   0.407  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.664  -0.152   0.050  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.950  -0.829   1.190  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.508  -1.011   0.853  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.860   0.307   0.607  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.631   0.173   0.268  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.411  -0.474   1.363  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.870  -0.588   0.987  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.486   0.752   0.728  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.930   0.698   0.367  1.00  0.00           C  
HETATM   13  C13 UNL     1      -5.119  -0.112  -0.892  1.00  0.00           C  
HETATM   14  C14 UNL     1      -6.563  -0.167  -1.273  1.00  0.00           C  
HETATM   15  O1  UNL     1      -7.381   0.430  -0.542  1.00  0.00           O  
HETATM   16  O2  UNL     1      -6.962  -0.859  -2.398  1.00  0.00           O  
HETATM   17  H1  UNL     1       6.602  -0.178  -2.603  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.820   0.206  -2.644  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.415  -1.204  -1.722  1.00  0.00           H  
HETATM   20  H4  UNL     1       6.908   0.832  -0.500  1.00  0.00           H  
HETATM   21  H5  UNL     1       5.398   1.703  -0.938  1.00  0.00           H  
HETATM   22  H6  UNL     1       5.615  -0.969   0.614  1.00  0.00           H  
HETATM   23  H7  UNL     1       5.205   0.617   1.317  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.618  -0.706  -0.891  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.263   0.870  -0.131  1.00  0.00           H  
HETATM   26  H10 UNL     1       3.454  -1.797   1.427  1.00  0.00           H  
HETATM   27  H11 UNL     1       3.096  -0.194   2.099  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.480  -1.578  -0.124  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.969  -1.640   1.590  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.024   1.043   1.419  1.00  0.00           H  
HETATM   31  H15 UNL     1       1.285   0.787  -0.325  1.00  0.00           H  
HETATM   32  H16 UNL     1      -0.977   1.248   0.219  1.00  0.00           H  
HETATM   33  H17 UNL     1      -0.686  -0.330  -0.697  1.00  0.00           H  
HETATM   34  H18 UNL     1      -1.044  -1.478   1.654  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.367   0.214   2.251  1.00  0.00           H  
HETATM   36  H20 UNL     1      -2.957  -1.279   0.100  1.00  0.00           H  
HETATM   37  H21 UNL     1      -3.446  -1.087   1.793  1.00  0.00           H  
HETATM   38  H22 UNL     1      -2.970   1.261  -0.119  1.00  0.00           H  
HETATM   39  H23 UNL     1      -3.394   1.337   1.668  1.00  0.00           H  
HETATM   40  H24 UNL     1      -5.580   0.339   1.194  1.00  0.00           H  
HETATM   41  H25 UNL     1      -5.230   1.752   0.090  1.00  0.00           H  
HETATM   42  H26 UNL     1      -4.583   0.420  -1.704  1.00  0.00           H  
HETATM   43  H27 UNL     1      -4.727  -1.147  -0.819  1.00  0.00           H  
HETATM   44  H28 UNL     1      -7.460  -0.439  -3.157  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   34   35
CONECT   10   11   36   37
CONECT   11   12   38   39
CONECT   12   13   40   41
CONECT   13   14   42   43
CONECT   14   15   15   16
CONECT   16   44
END

HMDB0000806
     RDKit          3D
Myristic acid
 44 43  0  0  0  0  0  0  0  0999 V2000
    5.6666   -0.1656   -2.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8305    0.7014   -0.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1443    0.0119    0.4072 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6644   -0.1516    0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9495   -0.8292    1.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5078   -1.0109    0.8528 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8600    0.3072    0.6066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6310    0.1727    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4111   -0.4743    1.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8704   -0.5884    0.9875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4855    0.7516    0.7277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9304    0.6982    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1195   -0.1117   -0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5625   -0.1672   -1.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3814    0.4303   -0.5425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9616   -0.8589   -2.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6020   -0.1777   -2.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8198    0.2055   -2.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4148   -1.2037   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9081    0.8318   -0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3980    1.7034   -0.9383 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6146   -0.9694    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2048    0.6173    1.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6177   -0.7061   -0.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2630    0.8705   -0.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545   -1.7974    1.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963   -0.1940    2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -1.5784   -0.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -1.6401    1.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0241    1.0434    1.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    0.7873   -0.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9771    1.2477    0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6861   -0.3296   -0.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0442   -1.4776    1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3673    0.2137    2.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9571   -1.2785    0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4463   -1.0870    1.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9696    1.2609   -0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3940    1.3370    1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5801    0.3386    1.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2300    1.7519    0.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5827    0.4198   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7272   -1.1471   -0.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4599   -0.4390   -3.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  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
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 16 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Tetradecanecarboxylic acid	ChEBI
14	ChEBI
14:0	ChEBI
14:00	ChEBI
Acide tetradecanoique	ChEBI
C14	ChEBI
CH3-[CH2]12-COOH	ChEBI
Myristinsaeure	ChEBI
N-Tetradecan-1-Oic acid	ChEBI
N-Tetradecanoic acid	ChEBI
N-Tetradecoic acid	ChEBI
Tetradecoic acid	ChEBI
Tetradecanoate	Kegg
1-Tetradecanecarboxylate	Generator
N-Tetradecan-1-Oate	Generator
N-Tetradecanoate	Generator
N-Tetradecoate	Generator
Tetradecoate	Generator
Tetradecanoic acid	Generator
Myristate	Generator
1-Tridecanecarboxylate	HMDB
1-Tridecanecarboxylic acid	HMDB
Crodacid	HMDB
Myristic acid pure	HMDB
Myristoate	HMDB
Myristoic acid	HMDB
Tetradecanoic (myristic) acid	HMDB
Acid, tetradecanoic	HMDB
Acid, myristic	HMDB
FA(14:0)	HMDB

Chemical Formula

C₁₄H₂₈O₂

Average Molecular Weight

228.3709

Monoisotopic Molecular Weight

228.20893014

IUPAC Name

tetradecanoic acid

Traditional Name

myristic acid

CAS Registry Number

544-63-8

SMILES

CCCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)

InChI Key

TUNFSRHWOTWDNC-UHFFFAOYSA-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
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:28875 )
straight-chain saturated fatty acid (CHEBI:28875 )
Straight chain fatty acids (C06424 )
Saturated fatty acids (C06424 )
Straight chain fatty acids (LMFA01010014 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	53.9 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0011 mg/mL	Not Available
LogP	6.11	SANGSTER (1993)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	159.209	30932474
[M-H]-	Not Available	159.209	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000218

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0017 g/L	ALOGPS
logP	6.1	ALOGPS
logP	5.37	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.95	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	12	ChemAxon
Refractivity	67.88 m³·mol⁻¹	ChemAxon
Polarizability	30.1 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]+	159.595	31661259
DarkChem	[M-H]-	158.274	31661259
AllCCS	[M+H]+	162.229	32859911
AllCCS	[M-H]-	162.934	32859911
DeepCCS	[M+H]+	157.952	30932474
DeepCCS	[M-H]-	153.929	30932474
DeepCCS	[M-2H]-	190.945	30932474
DeepCCS	[M+Na]+	166.841	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Myristic acid	CCCCCCCCCCCCCC(O)=O	2681.5	Standard polar	33892256
Myristic acid	CCCCCCCCCCCCCC(O)=O	1739.2	Standard non polar	33892256
Myristic acid	CCCCCCCCCCCCCC(O)=O	1776.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Myristic acid,1TMS,isomer #1	CCCCCCCCCCCCCC(=O)O[Si](C)(C)C	1846.1	Semi standard non polar	33892256
Myristic acid,1TBDMS,isomer #1	CCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2085.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Myristic acid GC-MS (1 TMS)	splash10-017i-2910000000-66b35fb8449ba9de9cd6	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Myristic acid GC-MS (Non-derivatized)	splash10-017i-2910000000-66b35fb8449ba9de9cd6	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Myristic acid GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-f45703c464ca75f98f26	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Myristic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9700000000-ec8d81e37bc3b8531c99	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Myristic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0079-9330000000-5ec01705dfacc992be28	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Myristic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Myristic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-06xx-9200000000-4fdd41f0461ff5186901	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-004i-0090000000-73ac1cfb8731e6318cc5	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-004i-1090000000-3aa768974da0ea81c1c9	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-004i-0090000000-22cd107a87b9acf058c5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-004i-0090000000-2f7bb32e4b42206d851d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-004i-2090000000-d45cffc15e2efbd45cd6	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-001i-9200000000-dbca68238dfebab35251	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-004r-9000000000-26827be8f8c2a4fbfd75	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid ESI-TOF 30V, Negative-QTOF	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid ESI-TOF 10V, Negative-QTOF	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid ESI-TOF 20V, Negative-QTOF	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid ESI-TOF , Negative-QTOF	splash10-0006-0090000000-110165b889d231d09d59	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid ESI-TOF 30V, Negative-QTOF	splash10-004i-0090000000-91f4f874b25705464fb0	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Myristic acid ESI-TOF 10V, Negative-QTOF	splash10-004i-0090000000-15225a799e0a0bcff7c7	2017-09-12	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 10V, Positive-QTOF	splash10-03di-0290000000-b88426a2003ceec57e30	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 20V, Positive-QTOF	splash10-01q9-5940000000-6c73dc0032502abe4fc4	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 40V, Positive-QTOF	splash10-052f-9300000000-bde9bfcd2889066fc853	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 10V, Positive-QTOF	splash10-03di-0290000000-b88426a2003ceec57e30	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 20V, Positive-QTOF	splash10-01q9-5940000000-6c73dc0032502abe4fc4	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 40V, Positive-QTOF	splash10-052f-9300000000-bde9bfcd2889066fc853	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 10V, Negative-QTOF	splash10-004i-0190000000-a32f141c7b5af0bc4de1	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 20V, Negative-QTOF	splash10-057i-1490000000-14bfb0d0344d7cf63443	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 40V, Negative-QTOF	splash10-0a4l-9400000000-512abb1322963024336f	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 10V, Negative-QTOF	splash10-004i-0190000000-a32f141c7b5af0bc4de1	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 20V, Negative-QTOF	splash10-057i-1490000000-14bfb0d0344d7cf63443	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Myristic acid 40V, Negative-QTOF	splash10-0a4l-9400000000-512abb1322963024336f	2015-05-27	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Adipose Tissue
Epidermis
Placenta
Prostate
Spleen

Pathways

Name	SMPDB/PathBank	KEGG
Fatty Acid Biosynthesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	25.0 (8.0-70.0) uM	Adult (>18 years old)	Both	Normal	8412012	details
Blood	Detected and Quantified	3.0 +/- 1.3 uM	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	7.16 +/- 3 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Blood	Detected and Quantified	9.3 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	15.464 +/- 4.024 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	2.7 +/- 1.5 uM	Adolescent (13-18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	2.1 +/- 0.9 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	1.1-3.3 uM	Adult (>18 years old)	Female	Normal	Geigy Scientific ...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22024767	details
Blood	Detected and Quantified	13.137 +/- 0.438 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	13.137 +/- 4.379 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	13.137 +/- 4.379 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	13.137 +/- 4.379 uM	Adult (>18 years old)	Male	Normal	17069347	details
Blood	Detected and Quantified	18.610 +/- 6.919 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	90 +/- 40 uM	Adult (>18 years old)	Female	Normal	14608088	details
Blood	Detected and Quantified	90 +/- 20 uM	Adult (>18 years old)	Male	Normal	14608088	details
Blood	Detected and Quantified	6.06 +/- 0.069 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	5.0 +/- 5.0 uM	Adult (>18 years old)	Not Specified	Normal	8412012	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23940645	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28587349	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	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	24029555	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected and Quantified	2.846 +/- 7.0937 nmol/g wet feces	Not Specified	Not Specified	Normal	19573517	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)	Not Specified	Normal	24421258	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	1268322	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21190195	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20809147	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	22727327	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.06 +/- 0.03 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	22148915	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Oesophageal cancer	22291914	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	22024767	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	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	25105552	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	28587349	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	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	23940645	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Oral squamous cell carcinoma (OSCC)	21190195	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Oral leukoplakia (OLK)	21190195	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	22148915	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Colorectal cancer
Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ] Cheng Y, Xie G, Chen T, Qiu Y, Zou X, Zheng M, Tan B, Feng B, Dong T, He P, Zhao L, Zhao A, Xu LX, Zhang Y, Jia W: Distinct urinary metabolic profile of human colorectal cancer. J Proteome Res. 2012 Feb 3;11(2):1354-63. doi: 10.1021/pr201001a. Epub 2011 Dec 28. [PubMed:22148915 ] Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ] 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 ] 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 ] 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 ] Wang X, Wang J, Rao B, Deng L: Gut flora profiling and fecal metabolite composition of colorectal cancer patients and healthy individuals. Exp Ther Med. 2017 Jun;13(6):2848-2854. doi: 10.3892/etm.2017.4367. Epub 2017 Apr 20. [PubMed:28587349 ]

Associated OMIM IDs

181500 (Schizophrenia)
114500 (Colorectal cancer)

External Links

DrugBank ID

DB08231

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28875

Food Biomarker Ontology

Not Available

VMH ID

TTDCA

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Greaves, W. S.; Linstead, R. P.; Shephard, B. R.; Thomas, S. L. S.; Weedon, B. C. L. Anodic syntheses. I. New syntheses of stearic, myristic, and other acids. Journal of the Chemical Society (1950), 3326-30.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4. [PubMed:11124748 ]
Dabadie H, Peuchant E, Bernard M, LeRuyet P, Mendy F: Moderate intake of myristic acid in sn-2 position has beneficial lipidic effects and enhances DHA of cholesteryl esters in an interventional study. J Nutr Biochem. 2005 Jun;16(6):375-82. [PubMed:15936650 ]
Majeti BK, Karmali PP, Madhavendra SS, Chaudhuri A: Example of fatty acid-loaded lipoplex in enhancing in vitro gene transfer efficacies of cationic amphiphile. Bioconjug Chem. 2005 May-Jun;16(3):676-84. [PubMed:15898737 ]
Schewe T, Hiebsch C: [Action of respiratory inhibitors on the electron transport system of Escherichia coli]. Acta Biol Med Ger. 1977;36(7-8):961-6. [PubMed:347849 ]
Curry S, Brick P, Franks NP: Fatty acid binding to human serum albumin: new insights from crystallographic studies. Biochim Biophys Acta. 1999 Nov 23;1441(2-3):131-40. [PubMed:10570241 ]
Kageura M, Hara K, Hieda Y, Takamoto M, Fujiwara Y, Fukuma Y, Kashimura S: [Screening of drugs and chemicals by wide-bore capillary gas chromatography with flame ionization and nitrogen phosphorus detectors]. Nihon Hoigaku Zasshi. 1989 Apr;43(2):161-5. [PubMed:2810891 ]
Zhu W, Smart EJ: Myristic acid stimulates endothelial nitric-oxide synthase in a CD36- and an AMP kinase-dependent manner. J Biol Chem. 2005 Aug 19;280(33):29543-50. Epub 2005 Jun 21. [PubMed:15970594 ]
Bhattacharya A, Ghosal SK: Permeation kinetics of ketotifen fumarate alone and in combination with hydrophobic permeation enhancers through human cadaver epidermis. Boll Chim Farm. 2000 Jul-Aug;139(4):177-81. [PubMed:11059101 ]
Matsubara M: [Structures and molecular recognition of MARCKS family proteins]. Seikagaku. 2005 Jan;77(1):50-5. [PubMed:15770953 ]
Kaminskas A, Zieden B, Elving B, Kristenson M, Abaravicius A, Bergdahl B, Olsson AG, Kucinskiene Z: Adipose tissue fatty acids in men from two populations with different cardiovascular risk: the LiVicordia study. Scand J Clin Lab Invest. 1999 May;59(3):227-32. [PubMed:10400167 ]
Brod SA, Malone M, Darcan S, Papolla M, Nelson L: Ingested interferon alpha suppresses type I diabetes in non-obese diabetic mice. Diabetologia. 1998 Oct;41(10):1227-32. [PubMed:9794112 ]
Pieterse Z, Jerling JC, Oosthuizen W, Kruger HS, Hanekom SM, Smuts CM, Schutte AE: Substitution of high monounsaturated fatty acid avocado for mixed dietary fats during an energy-restricted diet: effects on weight loss, serum lipids, fibrinogen, and vascular function. Nutrition. 2005 Jan;21(1):67-75. [PubMed:15661480 ]
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 ]

Only showing the first 10 proteins. There are 68 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Fatty acid synthase

General function:: Involved in transferase activity
Specific function:: Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:: FASN
Uniprot ID:: P49327
Molecular weight:: 273424.06

Reactions

Tetradecanoyl-[acp] + Water → Acyl-carrier protein + Myristic acid	details

Enzyme Details

2. Calcium-dependent phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. This isozyme hydrolyzes more efficiently L-alpha-1-palmitoyl-2-oleoyl phosphatidylcholine than L-alpha-1-palmitoyl-2-arachidonyl phosphatidylcholine, L-alpha-1-palmitoyl-2-arachidonyl phosphatidylethanolamine, or L-alpha-1-stearoyl-2-arachidonyl phosphatidylinositol. May be involved in the production of lung surfactant, the remodeling or regulation of cardiac muscle.
Gene Name:: PLA2G5
Uniprot ID:: P39877
Molecular weight:: 15674.065

Enzyme Details

3. Group IIF secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Hydrolyzes phosphatidylglycerol versus phosphatidylcholine with a 15-fold preference.
Gene Name:: PLA2G2F
Uniprot ID:: Q9BZM2
Molecular weight:: 23256.29

Enzyme Details

4. Cytosolic phospholipase A2

General function:: Involved in metabolic process
Specific function:: Selectively hydrolyzes arachidonyl phospholipids in the sn-2 position releasing arachidonic acid. Together with its lysophospholipid activity, it is implicated in the initiation of the inflammatory response.
Gene Name:: PLA2G4A
Uniprot ID:: P47712
Molecular weight:: 85210.19

Enzyme Details

5. Phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G1B
Uniprot ID:: P04054
Molecular weight:: 16359.535

Enzyme Details

6. Group 10 secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosphatidylethanolamine and phosphatidylcholine liposomes to those of phosphatidylserine.
Gene Name:: PLA2G10
Uniprot ID:: O15496
Molecular weight:: 18153.04

Enzyme Details

7. Galactoside-binding soluble lectin 13

General function:: Involved in sugar binding
Specific function:: Has lysophospholipase activity.
Gene Name:: LGALS13
Uniprot ID:: Q9UHV8
Molecular weight:: 16118.44

Enzyme Details

8. Group IIE secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name:: PLA2G2E
Uniprot ID:: Q9NZK7
Molecular weight:: 15988.525

Enzyme Details

9. Group XIIA secretory phospholipase A2

General function:: Involved in phospholipase A2 activity
Specific function:: PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Does not exhibit detectable activity toward sn-2-arachidonoyl- or linoleoyl-phosphatidylcholine or -phosphatidylethanolamine.
Gene Name:: PLA2G12A
Uniprot ID:: Q9BZM1
Molecular weight:: 21066.99

Enzyme Details

10. 85/88 kDa calcium-independent phospholipase A2

General function:: Involved in metabolic process
Specific function:: Catalyzes the release of fatty acids from phospholipids. It has been implicated in normal phospholipid remodeling, nitric oxide-induced or vasopressin-induced arachidonic acid release and in leukotriene and prostaglandin production. May participate in fas mediated apoptosis and in regulating transmembrane ion flux in glucose-stimulated B-cells. Has a role in cardiolipin (CL) deacylation. Required for both speed and directionality of monocyte MCP1/CCL2-induced chemotaxis through regulation of F-actin polymerization at the pseudopods. Isoform ankyrin-iPLA2-1 and isoform ankyrin-iPLA2-2, which lack the catalytic domain, are probably involved in the negative regulation of iPLA2 activity.
Gene Name:: PLA2G6
Uniprot ID:: O60733
Molecular weight:: 84092.635

Transporters

Enzyme Details

1. Long-chain fatty acid transport protein 1

General function:: Lipid transport and metabolism
Specific function:: Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:: SLC27A1
Uniprot ID:: Q6PCB7
Molecular weight:: 71107.5

Only showing the first 10 proteins. There are 68 proteins in total.

Show all enzymes and transporters

Showing metabocard for Myristic acid (HMDB0000806)

MOL for HMDB0000806 (Myristic acid)

3D MOL for HMDB0000806 (Myristic acid)

3D SDF for HMDB0000806 (Myristic acid)

3D-SDF for HMDB0000806 (Myristic acid)

PDB for HMDB0000806 (Myristic acid)

3D PDB for HMDB0000806 (Myristic acid)

SMILES for HMDB0000806 (Myristic acid)

INCHI for HMDB0000806 (Myristic acid)

Structure for HMDB0000806 (Myristic acid)

3D Structure for HMDB0000806 (Myristic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Transporters