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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-05-22 14:17:45 UTC

Update Date

2022-03-07 02:49:14 UTC

HMDB ID

HMDB0002261

Secondary Accession Numbers

HMDB02261

Metabolite Identification

Common Name

2-Hydroxymyristic acid

Description

2-Hydroxymyristic acid is an analog of myristic acid that becomes metabolically activated in cells to form 2-hydroxymyristoyl-CoA, a potent inhibitor of myristoyl-CoA:protein N-myristoyltransferase, the enzyme that catalyzes protein N-myristoylation. Treatment of T cells with 2-hydroxymyristic acid inhibits the myristoylation and alters the stability of p56lck. (PMID 8103677 ).

Structure

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

HMDB0002261
     RDKit          3D
2-Hydroxymyristic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
   -5.9565    2.0640   -0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7537    0.6024   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3025    0.1796   -0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452    0.9476    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0718    0.5988    0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8530   -0.8548    1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919   -1.2326    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129   -0.9569   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7721   -1.3562   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4560   -1.0654   -1.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8970   -1.4460   -1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7987   -0.8735   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829    0.5718   -0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0618    0.6397    0.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094    1.4632    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185    1.8574   -0.6687 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167    1.9371    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0565    2.6107   -0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7922    2.2637   -1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2988    2.5391    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1045    0.3055    0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3470   -0.0186   -0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807    0.3038   -1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841   -0.9141   -0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9560    0.6766    1.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597    2.0180    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5579    0.9457   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6240    1.1676    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -1.4155    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848   -1.1947    2.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -0.7150    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545   -2.3199    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -1.5022   -1.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575    0.1311   -0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973   -0.7982    0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8270   -2.4205    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973   -1.8486   -2.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988   -0.1244   -1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028   -1.3643   -2.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8873   -2.5847   -1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8235   -1.3670   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5407   -1.3199    0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6546    0.9144   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267    0.2806    1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5660    2.6746    1.6555 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
 13 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 17 45  1  0
M  END


  Mrv0541 02231219272D          

 17 16  0  0  0  0            999 V2000
   29.2872  -12.6201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7162  -11.7951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0016  -10.5575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2872  -11.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5727  -11.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8582  -11.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1437  -11.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4292  -11.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7148  -11.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0003  -11.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2857  -11.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5713  -11.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8568  -11.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1424  -11.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4278  -11.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7133  -11.7951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0016  -11.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  2 17  1  0  0  0  0
  3 17  2  0  0  0  0
  4  5  1  0  0  0  0
  4 17  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
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002261

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCCC(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-12-13(15)14(16)17/h13,15H,2-12H2,1H3,(H,16,17)

> <INCHI_KEY>
JYZJYKOZGGEXSX-UHFFFAOYSA-N

> <FORMULA>
C14H28O3

> <MOLECULAR_WEIGHT>
244.3703

> <EXACT_MASS>
244.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.700535802333608

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxytetradecanoic acid

> <ALOGPS_LOGP>
4.71

> <JCHEM_LOGP>
4.496379527

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.284148890034412

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.255557640559995

> <JCHEM_PKA_STRONGEST_BASIC>
-3.797528712514443

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
69.37379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxymyristic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002261
     RDKit          3D
2-Hydroxymyristic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
   -5.9565    2.0640   -0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7537    0.6024   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3025    0.1796   -0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452    0.9476    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0718    0.5988    0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8530   -0.8548    1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919   -1.2326    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129   -0.9569   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7721   -1.3562   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4560   -1.0654   -1.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8970   -1.4460   -1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7987   -0.8735   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829    0.5718   -0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0618    0.6397    0.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094    1.4632    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185    1.8574   -0.6687 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167    1.9371    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0565    2.6107   -0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7922    2.2637   -1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2988    2.5391    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1045    0.3055    0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3470   -0.0186   -0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807    0.3038   -1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841   -0.9141   -0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9560    0.6766    1.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597    2.0180    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5579    0.9457   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6240    1.1676    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -1.4155    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848   -1.1947    2.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -0.7150    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545   -2.3199    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -1.5022   -1.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575    0.1311   -0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973   -0.7982    0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8270   -2.4205    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973   -1.8486   -2.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988   -0.1244   -1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028   -1.3643   -2.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8873   -2.5847   -1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8235   -1.3670   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5407   -1.3199    0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6546    0.9144   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267    0.2806    1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5660    2.6746    1.6555 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
 13 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 17 45  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      54.669 -23.558   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      57.337 -22.018   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      56.003 -19.707   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      54.669 -22.018   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      53.336 -21.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      52.002 -22.018   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      50.668 -21.248   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      49.335 -22.018   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      48.001 -21.248   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      46.667 -22.018   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      45.333 -21.248   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      44.000 -22.018   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      42.666 -21.248   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      41.332 -22.018   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      39.999 -21.248   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.665 -22.018   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      56.003 -21.248   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2   17                                                            
CONECT    3   17                                                            
CONECT    4    1    5   17                                                  
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   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    2    3    4                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0002261
HETATM    1  C1  UNL     1      -5.957   2.064  -0.399  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.754   0.602  -0.163  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.302   0.180  -0.244  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.545   0.948   0.811  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.072   0.599   0.818  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.853  -0.855   1.091  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.392  -1.233   1.108  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.313  -0.957  -0.195  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.772  -1.356  -0.132  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.456  -1.065  -1.462  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.897  -1.446  -1.435  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.799  -0.873  -0.442  1.00  0.00           C  
HETATM   13  C13 UNL     1       5.083   0.572  -0.344  1.00  0.00           C  
HETATM   14  O1  UNL     1       6.062   0.640   0.754  1.00  0.00           O  
HETATM   15  C14 UNL     1       4.009   1.463   0.092  1.00  0.00           C  
HETATM   16  O2  UNL     1       3.118   1.857  -0.669  1.00  0.00           O  
HETATM   17  O3  UNL     1       3.917   1.937   1.419  1.00  0.00           O  
HETATM   18  H1  UNL     1      -5.057   2.611  -0.709  1.00  0.00           H  
HETATM   19  H2  UNL     1      -6.792   2.264  -1.121  1.00  0.00           H  
HETATM   20  H3  UNL     1      -6.299   2.539   0.563  1.00  0.00           H  
HETATM   21  H4  UNL     1      -6.104   0.305   0.867  1.00  0.00           H  
HETATM   22  H5  UNL     1      -6.347  -0.019  -0.865  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.881   0.304  -1.250  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.284  -0.914  -0.028  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.956   0.677   1.796  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.660   2.018   0.655  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.558   0.946  -0.093  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.624   1.168   1.673  1.00  0.00           H  
HETATM   29  H12 UNL     1      -2.299  -1.416   0.220  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.285  -1.195   2.039  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.147  -0.715   1.941  1.00  0.00           H  
HETATM   32  H15 UNL     1      -0.255  -2.320   1.311  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.178  -1.502  -1.004  1.00  0.00           H  
HETATM   34  H17 UNL     1       0.258   0.131  -0.437  1.00  0.00           H  
HETATM   35  H18 UNL     1       2.297  -0.798   0.649  1.00  0.00           H  
HETATM   36  H19 UNL     1       1.827  -2.420   0.105  1.00  0.00           H  
HETATM   37  H20 UNL     1       1.997  -1.849  -2.205  1.00  0.00           H  
HETATM   38  H21 UNL     1       2.199  -0.124  -1.914  1.00  0.00           H  
HETATM   39  H22 UNL     1       4.303  -1.364  -2.498  1.00  0.00           H  
HETATM   40  H23 UNL     1       3.887  -2.585  -1.268  1.00  0.00           H  
HETATM   41  H24 UNL     1       5.824  -1.367  -0.627  1.00  0.00           H  
HETATM   42  H25 UNL     1       4.541  -1.320   0.575  1.00  0.00           H  
HETATM   43  H26 UNL     1       5.655   0.914  -1.210  1.00  0.00           H  
HETATM   44  H27 UNL     1       5.527   0.281   1.510  1.00  0.00           H  
HETATM   45  H28 UNL     1       4.566   2.675   1.656  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   21   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   39   40
CONECT   12   13   41   42
CONECT   13   14   15   43
CONECT   14   44
CONECT   15   16   16   17
CONECT   17   45
END

HMDB0002261
     RDKit          3D
2-Hydroxymyristic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
   -5.9565    2.0640   -0.3992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7537    0.6024   -0.1629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3025    0.1796   -0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5452    0.9476    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0718    0.5988    0.8182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8530   -0.8548    1.0909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3919   -1.2326    1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3129   -0.9569   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7721   -1.3562   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4560   -1.0654   -1.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8970   -1.4460   -1.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7987   -0.8735   -0.4422 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0829    0.5718   -0.3436 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0618    0.6397    0.7535 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094    1.4632    0.0919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185    1.8574   -0.6687 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9167    1.9371    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0565    2.6107   -0.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7922    2.2637   -1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2988    2.5391    0.5626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1045    0.3055    0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3470   -0.0186   -0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807    0.3038   -1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841   -0.9141   -0.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9560    0.6766    1.7963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6597    2.0180    0.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5579    0.9457   -0.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6240    1.1676    1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -1.4155    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2848   -1.1947    2.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1471   -0.7150    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2545   -2.3199    1.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -1.5022   -1.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2575    0.1311   -0.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973   -0.7982    0.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8270   -2.4205    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973   -1.8486   -2.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1988   -0.1244   -1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028   -1.3643   -2.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8873   -2.5847   -1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8235   -1.3670   -0.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5407   -1.3199    0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6546    0.9144   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5267    0.2806    1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5660    2.6746    1.6555 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
 13 15  1  0
 15 16  2  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 17 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
alpha-Hydroxy-N-tetradecylic acid	ChEBI
alpha-Hydroxymyristic acid	ChEBI
a-Hydroxy-N-tetradecylate	Generator
a-Hydroxy-N-tetradecylic acid	Generator
alpha-Hydroxy-N-tetradecylate	Generator
Α-hydroxy-N-tetradecylate	Generator
Α-hydroxy-N-tetradecylic acid	Generator
a-Hydroxymyristate	Generator
a-Hydroxymyristic acid	Generator
alpha-Hydroxymyristate	Generator
Α-hydroxymyristate	Generator
Α-hydroxymyristic acid	Generator
2-Hydroxymyristate	Generator
2-Hydroxy-myristic-acid	HMDB
2-Hydroxytetradecanoate	HMDB
2-Hydroxytetradecanoic acid	HMDB
DL-a-Hydroxymyristate	HMDB
DL-a-Hydroxymyristic acid	HMDB
DL-alpha-Hydroxymyristate	HMDB
DL-alpha-Hydroxymyristic acid	HMDB

Chemical Formula

C₁₄H₂₈O₃

Average Molecular Weight

244.3703

Monoisotopic Molecular Weight

244.203844762

IUPAC Name

2-hydroxytetradecanoic acid

Traditional Name

2-hydroxymyristic acid

CAS Registry Number

2507-55-3

SMILES

CCCCCCCCCCCCC(O)C(O)=O

InChI Identifier

InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-12-13(15)14(16)17/h13,15H,2-12H2,1H3,(H,16,17)

InChI Key

JYZJYKOZGGEXSX-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
Hydroxy fatty acid
Alpha-hydroxy acid
Hydroxy acid
Monosaccharide
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:59270 )
2-hydroxy fatty acid (CHEBI:59270 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0002261)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)
Urine (HMDB: HMDB0002261)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002261)

Source

Endogenous

Endogenous (HMDB: HMDB0002261)

Animal

Animal (HMDB: HMDB0002261)

Exogenous

Food

Food (HMDB: HMDB0002261)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0002261)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002261)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002261)

Lipid metabolism pathway (HMDB: HMDB0002261)

Cellular process

Cell signaling (HMDB: HMDB0002261)

Biochemical process

Lipid transport (HMDB: HMDB0002261)

Role

Biological role

Energy source (HMDB: HMDB0002261)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002261)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	51.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	377.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	17.82 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.150 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	4.71	ALOGPS
logP	4.5	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.26	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	69.37 m³·mol⁻¹	ChemAxon
Polarizability	30.7 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	163.961	31661259
DarkChem	[M-H]-	161.19	31661259
DeepCCS	[M+H]+	162.737	30932474
DeepCCS	[M-H]-	158.716	30932474
DeepCCS	[M-2H]-	196.227	30932474
DeepCCS	[M+Na]+	171.926	30932474
AllCCS	[M+H]+	166.0	32859911
AllCCS	[M+H-H2O]+	162.7	32859911
AllCCS	[M+NH4]+	169.1	32859911
AllCCS	[M+Na]+	170.0	32859911
AllCCS	[M-H]-	164.3	32859911
AllCCS	[M+Na-2H]-	165.2	32859911
AllCCS	[M+HCOO]-	166.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.91 minutes	32390414
Predicted by Siyang on May 30, 2022	17.9489 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.53 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	34.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2626.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	467.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	194.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	243.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	465.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	776.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	751.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1643.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	522.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1626.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	588.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	432.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	563.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	429.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	21.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxymyristic acid	CCCCCCCCCCCCC(O)C(O)=O	2890.7	Standard polar	33892256
2-Hydroxymyristic acid	CCCCCCCCCCCCC(O)C(O)=O	1858.5	Standard non polar	33892256
2-Hydroxymyristic acid	CCCCCCCCCCCCC(O)C(O)=O	1931.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxymyristic acid,1TMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C)C(=O)O	1986.3	Semi standard non polar	33892256
2-Hydroxymyristic acid,1TMS,isomer #2	CCCCCCCCCCCCC(O)C(=O)O[Si](C)(C)C	1952.9	Semi standard non polar	33892256
2-Hydroxymyristic acid,2TMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2029.7	Semi standard non polar	33892256
2-Hydroxymyristic acid,1TBDMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(=O)O	2218.6	Semi standard non polar	33892256
2-Hydroxymyristic acid,1TBDMS,isomer #2	CCCCCCCCCCCCC(O)C(=O)O[Si](C)(C)C(C)(C)C	2185.8	Semi standard non polar	33892256
2-Hydroxymyristic acid,2TBDMS,isomer #1	CCCCCCCCCCCCC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2468.2	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 - 2-Hydroxymyristic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-9700000000-8493ca6732d2b7ebf6b1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxymyristic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9242000000-206629d5379d5a4a3a86	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxymyristic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxymyristic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 10V, Positive-QTOF	splash10-002b-0390000000-fa16fe269769b95e9682	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 20V, Positive-QTOF	splash10-05ot-3930000000-58ff17a1c4711e739574	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 40V, Positive-QTOF	splash10-052f-9400000000-1ceac1323899f5bc74f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 10V, Negative-QTOF	splash10-0006-0290000000-7ba586681c0bf7368a66	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 20V, Negative-QTOF	splash10-002e-0960000000-5b0f96b6ff1eb7d2407c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 40V, Negative-QTOF	splash10-014m-6900000000-a272f854b23f304deab7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 10V, Negative-QTOF	splash10-0006-0090000000-5bf7291211ccfc840371	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 20V, Negative-QTOF	splash10-0006-1290000000-b279ed37b3233bd67aba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 40V, Negative-QTOF	splash10-0006-9000000000-19fc4b5fb13d8c68f49b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 10V, Positive-QTOF	splash10-0002-7590000000-69d3171bbb95f941fb9f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 20V, Positive-QTOF	splash10-0a4i-9200000000-43bbc1f0c7641b18f6f3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxymyristic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-5a9991dd3dc9260adadb	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

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	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 ]
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

FDB022931

KNApSAcK ID

Not Available

Chemspider ID

1508

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6579

PubChem Compound

1563

PDB ID

Not Available

ChEBI ID

59270

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1027761

References

Synthesis Reference

Skipski, Vladimir P.; Arfin, Stuart M.; Rapport, Maurice M. Paper chromatography of saturated, unsaturated, and hydroxy fatty acids. Archives of Biochemistry and Biophysics (1960), 87 259-65.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Misasi R, Sorice M, Griggi T, d'Agostino F, Garofalo T, Masala C, Pontieri GM, Lenti L: GM3 as a target of anti-lymphocytic ganglioside antibodies in AIDS patients. Clin Immunol Immunopathol. 1993 Jun;67(3 Pt 1):216-23. [PubMed:8500269 ]
Nadler MJ, Harrison ML, Ashendel CL, Cassady JM, Geahlen RL: Treatment of T cells with 2-hydroxymyristic acid inhibits the myristoylation and alters the stability of p56lck. Biochemistry. 1993 Sep 7;32(35):9250-5. [PubMed:8103677 ]

Showing metabocard for 2-Hydroxymyristic acid (HMDB0002261)

MOL for HMDB0002261 (2-Hydroxymyristic acid)

3D MOL for HMDB0002261 (2-Hydroxymyristic acid)

3D SDF for HMDB0002261 (2-Hydroxymyristic acid)

3D-SDF for HMDB0002261 (2-Hydroxymyristic acid)

PDB for HMDB0002261 (2-Hydroxymyristic acid)

3D PDB for HMDB0002261 (2-Hydroxymyristic acid)

SMILES for HMDB0002261 (2-Hydroxymyristic acid)

INCHI for HMDB0002261 (2-Hydroxymyristic acid)

Structure for HMDB0002261 (2-Hydroxymyristic acid)

3D Structure for HMDB0002261 (2-Hydroxymyristic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra