MiMeDB: Showing metabocard for 2-Hydroxymyristic acid (MMDBc0000588)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:50:34 UTC

Update Date

2024-04-30 19:33:09 UTC

Metabolite ID

MMDBc0000588

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>
MMDBc0000588

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₄H₂₈O₃

Average Mass

244.3703

Monoisotopic Mass

244.203844762

IUPAC Name

2-hydroxytetradecanoic acid

Traditional Name

2-hydroxymyristic acid

CAS Registry Number

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002g-9700000000-8493ca6732d2b7ebf6b1	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9242000000-206629d5379d5a4a3a86	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0390000000-fa16fe269769b95e9682	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05ot-3930000000-58ff17a1c4711e739574	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9400000000-1ceac1323899f5bc74f3	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0290000000-7ba586681c0bf7368a66	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002e-0960000000-5b0f96b6ff1eb7d2407c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014m-6900000000-a272f854b23f304deab7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-5bf7291211ccfc840371	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-1290000000-b279ed37b3233bd67aba	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-19fc4b5fb13d8c68f49b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-7590000000-69d3171bbb95f941fb9f	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9200000000-43bbc1f0c7641b18f6f3	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-5a9991dd3dc9260adadb	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0002261

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

References

Synthesis Reference

Not Available

General References

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. doi: 10.1021/bi00086a034. [PubMed:8103677 ]
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. doi: 10.1006/clin.1993.1068. [PubMed:8500269 ]

Showing metabocard for 2-Hydroxymyristic acid (MMDBc0000588)

MOL for #<Metabolite:0x00007fdb50a6a1e8>

3D MOL for #<Metabolite:0x00007fdb50a6a1e8>

3D SDF for #<Metabolite:0x00007fdb50a6a1e8>

3D-SDF for #<Metabolite:0x00007fdb50a6a1e8>

PDB for #<Metabolite:0x00007fdb50a6a1e8>

3D PDB for #<Metabolite:0x00007fdb50a6a1e8>

SMILES for #<Metabolite:0x00007fdb50a6a1e8>

INCHI for #<Metabolite:0x00007fdb50a6a1e8>

Structure for #<Metabolite:0x00007fdb50a6a1e8>

3D Structure for #<Metabolite:0x00007fdb50a6a1e8>