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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:41 UTC

Update Date

2023-02-21 17:16:15 UTC

HMDB ID

HMDB0002203

Secondary Accession Numbers

HMDB02203

Metabolite Identification

Common Name

3-Hydroxycapric acid

Description

3-Hydroxycapric acid (CAS: 14292-26-3) is a normally occurring carboxylic acid in human blood plasma. Medium- and long-chain 3-hydroxymonocarboxylic acids represent intermediates in the beta-oxidation of fatty acids. They accumulate in the plasma of patients with an inherited deficiency of long-chain 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35) (PMID: 1912723 ). 3-Hydroxyacyl-CoA dehydrogenase (HADH) deficiency has been described in diverse clinical cases: juvenile-onset recurrent myoglobinuria, hypoketotic hypoglycemic encephalopathy, hypertrophic/dilatative cardiomyopathy, sudden infant death, and fulminant hepatic failure (OMIM: 231530 ). 3-Hydroxycapric acid has some shape-transforming action on the membrane of intact human erythrocytes (PMID: 7318031 ).

Structure

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

HMDB0002203
     RDKit          3D
3-Hydroxycapric acid
 33 32  0  0  0  0  0  0  0  0999 V2000
    4.3136    0.9773   -0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0728    0.0818    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089   -1.0193    0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -0.6242   -0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0086    0.1958    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3826    0.5672    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -0.6213   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308   -0.3342   -0.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7035    0.4010   -1.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5454    0.2272    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    0.4352   -0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2388    1.5897   -0.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7731   -0.5965   -0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966    1.2898   -0.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652    0.4247   -1.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849    1.8983   -0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456    0.6846    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0677   -0.4092    0.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173   -1.6219   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.7126    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -1.5973   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6765   -0.1449   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8730   -0.3797    1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445    1.1259    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315    1.1768   -0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    1.2659    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688   -1.2581   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -1.2440    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0790   -1.3520   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    1.2909   -1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1809    1.2393    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620   -0.3932    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5989   -1.5632   -0.1698 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
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
M  END

HMDB0002203
     RDKit          3D
3-Hydroxycapric acid
 33 32  0  0  0  0  0  0  0  0999 V2000
    4.3136    0.9773   -0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0728    0.0818    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089   -1.0193    0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -0.6242   -0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0086    0.1958    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3826    0.5672    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -0.6213   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308   -0.3342   -0.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7035    0.4010   -1.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5454    0.2272    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    0.4352   -0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2388    1.5897   -0.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7731   -0.5965   -0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966    1.2898   -0.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652    0.4247   -1.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849    1.8983   -0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456    0.6846    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0677   -0.4092    0.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173   -1.6219   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.7126    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -1.5973   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6765   -0.1449   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8730   -0.3797    1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445    1.1259    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315    1.1768   -0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    1.2659    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688   -1.2581   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -1.2440    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0790   -1.3520   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    1.2909   -1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1809    1.2393    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620   -0.3932    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5989   -1.5632   -0.1698 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
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
M  END

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8662.8668663.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8661.5318663.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8660.1978663.064   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8658.8628663.832   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8657.5288663.064   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8658.8628665.373   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8661.5318665.373   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8664.2008663.832   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.5368663.064   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.8688663.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8668.2048663.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8669.5368663.832   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8670.8728663.064   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0002203
HETATM    1  C1  UNL     1       4.314   0.977  -0.888  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.073   0.082   0.312  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.109  -1.019   0.057  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.729  -0.624  -0.337  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.009   0.196   0.678  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.383   0.567   0.221  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.233  -0.621  -0.052  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.631  -0.334  -0.495  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.703   0.401  -1.655  1.00  0.00           O  
HETATM   10  C9  UNL     1      -3.545   0.227   0.538  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.868   0.435  -0.101  1.00  0.00           C  
HETATM   12  O2  UNL     1      -5.239   1.590  -0.511  1.00  0.00           O  
HETATM   13  O3  UNL     1      -5.773  -0.597  -0.290  1.00  0.00           O  
HETATM   14  H1  UNL     1       5.397   1.290  -0.933  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.065   0.425  -1.818  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.685   1.898  -0.798  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.846   0.685   1.210  1.00  0.00           H  
HETATM   18  H5  UNL     1       5.068  -0.409   0.530  1.00  0.00           H  
HETATM   19  H6  UNL     1       3.517  -1.622  -0.809  1.00  0.00           H  
HETATM   20  H7  UNL     1       3.045  -1.713   0.921  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.161  -1.597  -0.425  1.00  0.00           H  
HETATM   22  H9  UNL     1       1.676  -0.145  -1.327  1.00  0.00           H  
HETATM   23  H10 UNL     1       0.873  -0.380   1.633  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.544   1.126   0.959  1.00  0.00           H  
HETATM   25  H12 UNL     1      -0.232   1.177  -0.712  1.00  0.00           H  
HETATM   26  H13 UNL     1      -0.815   1.266   0.961  1.00  0.00           H  
HETATM   27  H14 UNL     1      -0.769  -1.258  -0.833  1.00  0.00           H  
HETATM   28  H15 UNL     1      -1.299  -1.244   0.864  1.00  0.00           H  
HETATM   29  H16 UNL     1      -3.079  -1.352  -0.764  1.00  0.00           H  
HETATM   30  H17 UNL     1      -3.100   1.291  -1.429  1.00  0.00           H  
HETATM   31  H18 UNL     1      -3.181   1.239   0.889  1.00  0.00           H  
HETATM   32  H19 UNL     1      -3.662  -0.393   1.440  1.00  0.00           H  
HETATM   33  H20 UNL     1      -5.599  -1.563  -0.170  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17   18
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8   27   28
CONECT    8    9   10   29
CONECT    9   30
CONECT   10   11   31   32
CONECT   11   12   12   13
CONECT   13   33
END

HMDB0002203
     RDKit          3D
3-Hydroxycapric acid
 33 32  0  0  0  0  0  0  0  0999 V2000
    4.3136    0.9773   -0.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0728    0.0818    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1089   -1.0193    0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7289   -0.6242   -0.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0086    0.1958    0.6776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3826    0.5672    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2327   -0.6213   -0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6308   -0.3342   -0.4953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7035    0.4010   -1.6547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5454    0.2272    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    0.4352   -0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2388    1.5897   -0.5115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7731   -0.5965   -0.2899 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3966    1.2898   -0.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0652    0.4247   -1.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849    1.8983   -0.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456    0.6846    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0677   -0.4092    0.5297 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173   -1.6219   -0.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0454   -1.7126    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -1.5973   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6765   -0.1449   -1.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8730   -0.3797    1.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445    1.1259    0.9586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315    1.1768   -0.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    1.2659    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7688   -1.2581   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2986   -1.2440    0.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0790   -1.3520   -0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004    1.2909   -1.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1809    1.2393    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620   -0.3932    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5989   -1.5632   -0.1698 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
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  6
  9 30  1  0
 10 31  1  0
 10 32  1  0
 13 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxycaprate	Generator
(S)-3-Hydroxydecanoate	HMDB
(+)-3-Hydroxydecanoate	HMDB
(+)-3-Hydroxydecanoic acid	HMDB
(3S)-3-Hydroxydecanoate	HMDB
(3S)-3-Hydroxydecanoic acid	HMDB
(±)-3-hydroxydecanoate	HMDB
(±)-3-hydroxydecanoic acid	HMDB
3(S)-Hydroxydecanoate	HMDB
3(S)-Hydroxydecanoic acid	HMDB
3-Hydroxidecanoate	HMDB
3-Hydroxidecanoic acid	HMDB
3-Hydroxydecanoate	HMDB
3-Hydroxydecanoic acid	HMDB
FA(10:0(3-OH))	HMDB
FA(10:0(3S-OH))	HMDB
L-beta-Hydroxydecanoate	HMDB
L-beta-Hydroxydecanoic acid	HMDB
L-Β-hydroxydecanoate	HMDB
L-Β-hydroxydecanoic acid	HMDB
S-3-Hydroxydecanoate	HMDB
S-3-Hydroxydecanoic acid	HMDB
beta-Hydroxycaprate	HMDB
beta-Hydroxycapric acid	HMDB
beta-Hydroxydecanoate	HMDB
beta-Hydroxydecanoic acid	HMDB
Β-hydroxycaprate	HMDB
Β-hydroxycapric acid	HMDB
Β-hydroxydecanoate	HMDB
Β-hydroxydecanoic acid	HMDB
3-Hydroxycapric acid	HMDB

Chemical Formula

C₁₀H₂₀O₃

Average Molecular Weight

188.267

Monoisotopic Molecular Weight

188.141244504

IUPAC Name

(3S)-3-hydroxydecanoic acid

Traditional Name

S-3-hydroxydecanoic acid

CAS Registry Number

19526-23-9

SMILES

CCCCCCC[C@H](O)CC(O)=O

InChI Identifier

InChI=1S/C10H20O3/c1-2-3-4-5-6-7-9(11)8-10(12)13/h9,11H,2-8H2,1H3,(H,12,13)/t9-/m0/s1

InChI Key

FYSSBMZUBSBFJL-VIFPVBQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Medium-chain hydroxy acids and derivatives

Direct Parent

Medium-chain hydroxy acids and derivatives

Alternative Parents

Substituents

Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-hydroxy monocarboxylic acid (CHEBI:37371 )
Hydroxy fatty acids (LMFA01050246 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9337379)

Cellular substructure

Membrane (HMDB: HMDB0002203)
Cell membrane (HMDB: HMDB0002203)

Organ

Placenta (HMDB: HMDB0002203)

Excreta

Biofluid or Excreta

Feces (PMID: 27015276)
Urine (PMID: 1870421)

Source

Endogenous

Endogenous (HMDB: HMDB0002203)

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)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.74 g/L	ALOGPS
logP	2.6	ALOGPS
logP	2.36	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-2.8	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	8	ChemAxon
Refractivity	50.99 m³·mol⁻¹	ChemAxon
Polarizability	22.16 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
DeepCCS	[M+H]+	147.439	30932474
DeepCCS	[M-H]-	143.414	30932474
DeepCCS	[M-2H]-	180.888	30932474
DeepCCS	[M+Na]+	156.553	30932474
AllCCS	[M+H]+	147.7	32859911
AllCCS	[M+H-H2O]+	143.9	32859911
AllCCS	[M+NH4]+	151.2	32859911
AllCCS	[M+Na]+	152.2	32859911
AllCCS	[M-H]-	146.7	32859911
AllCCS	[M+Na-2H]-	148.1	32859911
AllCCS	[M+HCOO]-	149.7	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.	6.06 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6304 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.06 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	48.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1856.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	304.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	274.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	497.0 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	493.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	99.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	998.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	389.0 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	1273.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	321.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	328.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	396.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	207.6 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	87.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxycapric acid	CCCCCCC[C@H](O)CC(O)=O	2633.0	Standard polar	33892256
3-Hydroxycapric acid	CCCCCCC[C@H](O)CC(O)=O	1487.9	Standard non polar	33892256
3-Hydroxycapric acid	CCCCCCC[C@H](O)CC(O)=O	1569.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxycapric acid,1TMS,isomer #1	CCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C	1582.5	Semi standard non polar	33892256
3-Hydroxycapric acid,1TMS,isomer #2	CCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C	1570.1	Semi standard non polar	33892256
3-Hydroxycapric acid,2TMS,isomer #1	CCCCCCC[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1665.8	Semi standard non polar	33892256
3-Hydroxycapric acid,1TBDMS,isomer #1	CCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C	1804.3	Semi standard non polar	33892256
3-Hydroxycapric acid,1TBDMS,isomer #2	CCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C	1799.5	Semi standard non polar	33892256
3-Hydroxycapric acid,2TBDMS,isomer #1	CCCCCCC[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2122.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Hydroxycapric acid GC-MS (2 TMS)	splash10-0f89-3950000000-4dc7506e884d7c6679d5	2019-10-24	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Hydroxycapric acid GC-MS (Non-derivatized)	splash10-0f89-3950000000-4dc7506e884d7c6679d5	2019-10-24	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxycapric 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Hydroxycapric acid LC-ESI-IT , negative-QTOF	splash10-0a4i-9000000000-616c6c1304ee3dc8333d	2019-10-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 10V, Negative-QTOF	splash10-000i-2900000000-b48a55f35e3a261db7a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 20V, Negative-QTOF	splash10-0a4i-9400000000-9bf57a4f1bdff00e64dc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 40V, Negative-QTOF	splash10-0006-9000000000-24256337cd6db4163a77	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 10V, Positive-QTOF	splash10-052r-9800000000-05fd88a0d973888af6c8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 20V, Positive-QTOF	splash10-0a4i-9000000000-6e5509a032d59c16205c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxycapric acid 40V, Positive-QTOF	splash10-0a4l-9000000000-2cfe9add86e448abe675	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Placenta

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	25037050	details
Urine	Detected and Quantified	6.00540 +/- 5.405 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	1870421	details
Urine	Detected and Quantified	5.405 +/- 9.609 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	1870421	details
Urine	Detected and Quantified	29.426 +/- 23.421 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	1870421	details
Urine	Detected and Quantified	31.829 +/- 13.212 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	1870421	details
Urine	Detected and Quantified	88.279 +/- 75.668 umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	1870421	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	ND-25 uM	Children (1-13 years old)	Male	3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency	9337379	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
Urine	Detected and Quantified	171.754-696.0255 umol/mmol creatinine	Infant (0-1 year old)	Not Specified	3-Hydroxydicarboxylic aciduria	1870421	details

Associated Disorders and Diseases

Disease References

3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency
Thompson GN, Hsu BY, Pitt JJ, Treacy E, Stanley CA: Fasting hypoketotic coma in a child with deficiency of mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase. N Engl J Med. 1997 Oct 23;337(17):1203-7. doi: 10.1056/NEJM199710233371704. [PubMed:9337379 ]
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 ]
3-Hydroxydicarboxylic aciduria
Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Urinary 3-hydroxydicarboxylic acids in pathophysiology of metabolic disorders with dicarboxylic aciduria. Metabolism. 1991 Jul;40(7):676-82. [PubMed:1870421 ] Hagenfeldt L, von Dobeln U, Holme E, Alm J, Brandberg G, Enocksson E, Lindeberg L: 3-Hydroxydicarboxylic aciduria--a fatty acid oxidation defect with severe prognosis. J Pediatr. 1990 Mar;116(3):387-92. [PubMed:2308028 ]

Associated OMIM IDs

605911 (3-Hydroxy-3-Methylglutaryl-CoA Synthase Deficiency)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022904

KNApSAcK ID

Not Available

Chemspider ID

4472224

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Myrmicacin

METLIN ID

6544

PubChem Compound

5312799

PDB ID

Not Available

ChEBI ID

37371

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kondo, Kiyoshi; Ryu, Yuchin. 3-Hydroxydecanoic acid. Jpn. Kokai Tokkyo Koho (1972), 5 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Grupe A, Spiteller G: New polar acid metabolites in human urine. J Chromatogr. 1981 Dec 11;226(2):301-14. [PubMed:7320161 ]
Dorland L, Ketting D, Bruinvis L, Duran M: Medium- and long-chain 3-hydroxymonocarboxylic acids: analysis by gas chromatography combined with mass spectrometry. Biomed Chromatogr. 1991 Jul;5(4):161-4. [PubMed:1912723 ]
Kanaho Y, Sato T, Fujii T, Iwanami Y, Iwadare T, Orito K: Shape-transforming action of myrmicacin (3-hydroxydecanoic acid) and some related compounds on the membrane of intact human erythrocytes. Chem Pharm Bull (Tokyo). 1981 Oct;29(10):3063-6. [PubMed:7318031 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for 3-Hydroxycapric acid (HMDB0002203)

MOL for HMDB0002203 (3-Hydroxycapric acid)

3D MOL for HMDB0002203 (3-Hydroxycapric acid)

3D SDF for HMDB0002203 (3-Hydroxycapric acid)

3D-SDF for HMDB0002203 (3-Hydroxycapric acid)

PDB for HMDB0002203 (3-Hydroxycapric acid)

3D PDB for HMDB0002203 (3-Hydroxycapric acid)

SMILES for HMDB0002203 (3-Hydroxycapric acid)

INCHI for HMDB0002203 (3-Hydroxycapric acid)

Structure for HMDB0002203 (3-Hydroxycapric acid)

3D Structure for HMDB0002203 (3-Hydroxycapric acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra