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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-04-11 22:17:03 UTC

Update Date

2021-09-14 14:58:20 UTC

HMDB ID

HMDB0061656

Secondary Accession Numbers

HMDB0094672
HMDB61656
HMDB94672

Metabolite Identification

Common Name

3-Hydroxytetradecanoic acid

Description

3-Hydroxytetradecanoic acid (CAS: 1961-72-4) is a long-chain hydroxy fatty acid. In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. (R)-3-Hydroxytetradecanoic acid is the most common fatty acid constituent of the lipid A component of bacterial lipopolysaccharides (LPS). 3-Hydroxytetradecanoic acid can be found in feces

Structure

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

HMDB0061656
     RDKit          3D
3-Hydroxytetradecanoic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
    6.2595    2.4077    0.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5950    1.3658   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    1.0105    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5379   -0.0468   -0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2511   -0.3322    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4120   -1.3697   -0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1474   -1.5457    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857   -2.5701   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -2.1722   -1.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9466   -0.8665   -1.5501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2093   -0.9035   -0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9221    0.4464   -0.7724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0125    1.4063   -0.2773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1224    0.3982    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8483    1.6911    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4222    2.6184   -0.6305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9820    1.8725    0.8375 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7882    1.9166    1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4458    3.0301    1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8998    3.0927    0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2561    0.4726   -0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4837    1.7591   -1.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4950    0.6247    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6636    1.9270    0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2129   -0.9446   -0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4384    0.2605   -1.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6558    0.5936    0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -0.7242    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619   -1.0645   -1.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -2.3607   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -0.5998    0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -1.8594    1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6740   -2.6124    0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209   -3.5882   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8874   -2.9863   -1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649   -2.1276   -2.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2402   -0.5871   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720   -0.0520   -1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8470   -1.7259   -1.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737   -0.9815    0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2108    0.6918   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4136    1.8735    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7758   -0.4484   -0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8057    0.2435    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2032    2.7666    1.2704 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
 12 14  1  0
 14 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  6
 13 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  0
M  END


  Mrv1652303072001022D          

 17 16  0  0  0  0            999 V2000
 9997.9637 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2489 9998.4815    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9996.5339 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8190 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1042 9998.0698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8190 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2489 9999.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.6785 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3942 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8234 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.1078 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.1106 9998.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.3956 9998.4854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.6817 9998.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.9666 9998.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.2528 9998.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.5371 9998.4815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  8  9  1  0  0  0  0
 11 10  1  0  0  0  0
  9 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 10 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061656

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCC[C@H](O)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)/t13-/m0/s1

> <INCHI_KEY>
ATRNZOYKSNPPBF-ZDUSSCGKSA-N

> <FORMULA>
C14H28O3

> <MOLECULAR_WEIGHT>
244.375

> <EXACT_MASS>
244.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
30.618733757475574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-hydroxytetradecanoic acid

> <ALOGPS_LOGP>
4.69

> <JCHEM_LOGP>
4.136634380666667

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.288498288670866

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.671850167040888

> <JCHEM_PKA_STRONGEST_BASIC>
-2.798587426318786

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
69.3971

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.99e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-myristic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061656
     RDKit          3D
3-Hydroxytetradecanoic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
    6.2595    2.4077    0.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5950    1.3658   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    1.0105    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5379   -0.0468   -0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2511   -0.3322    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4120   -1.3697   -0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1474   -1.5457    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857   -2.5701   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -2.1722   -1.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9466   -0.8665   -1.5501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2093   -0.9035   -0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9221    0.4464   -0.7724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0125    1.4063   -0.2773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1224    0.3982    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8483    1.6911    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4222    2.6184   -0.6305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9820    1.8725    0.8375 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7882    1.9166    1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4458    3.0301    1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8998    3.0927    0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2561    0.4726   -0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4837    1.7591   -1.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4950    0.6247    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6636    1.9270    0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2129   -0.9446   -0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4384    0.2605   -1.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6558    0.5936    0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -0.7242    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619   -1.0645   -1.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -2.3607   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -0.5998    0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -1.8594    1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6740   -2.6124    0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209   -3.5882   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8874   -2.9863   -1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649   -2.1276   -2.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2402   -0.5871   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720   -0.0520   -1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8470   -1.7259   -1.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737   -0.9815    0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2108    0.6918   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4136    1.8735    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7758   -0.4484   -0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8057    0.2435    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2032    2.7666    1.2704 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
 12 14  1  0
 14 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  6
 13 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  0
M  END

HEADER    PROTEIN                                 07-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-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    8668.2048663.064   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.8688663.832   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8676.2068663.071   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8674.8728663.839   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8673.5398663.068   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8672.2048663.835   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8670.8728663.064   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8669.5368663.832   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   11                                                       
CONECT   10   11   17                                                       
CONECT   11   10    9                                                       
CONECT   12   13                                                            
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   10                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0061656
HETATM    1  C1  UNL     1       6.259   2.408   0.712  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.595   1.366  -0.161  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.273   1.011   0.483  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.538  -0.047  -0.352  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.251  -0.332   0.358  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.412  -1.370  -0.360  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.147  -1.546   0.482  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.786  -2.570  -0.135  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.218  -2.172  -1.510  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.947  -0.867  -1.550  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.209  -0.903  -0.700  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.922   0.446  -0.772  1.00  0.00           C  
HETATM   13  O1  UNL     1      -3.012   1.406  -0.277  1.00  0.00           O  
HETATM   14  C13 UNL     1      -5.122   0.398   0.126  1.00  0.00           C  
HETATM   15  C14 UNL     1      -5.848   1.691   0.089  1.00  0.00           C  
HETATM   16  O2  UNL     1      -5.422   2.618  -0.630  1.00  0.00           O  
HETATM   17  O3  UNL     1      -6.982   1.873   0.838  1.00  0.00           O  
HETATM   18  H1  UNL     1       6.788   1.917   1.577  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.446   3.030   1.172  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.900   3.093   0.152  1.00  0.00           H  
HETATM   21  H4  UNL     1       6.256   0.473  -0.142  1.00  0.00           H  
HETATM   22  H5  UNL     1       5.484   1.759  -1.187  1.00  0.00           H  
HETATM   23  H6  UNL     1       4.495   0.625   1.490  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.664   1.927   0.601  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.213  -0.945  -0.343  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.438   0.260  -1.391  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.656   0.594   0.396  1.00  0.00           H  
HETATM   28  H11 UNL     1       2.500  -0.724   1.365  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.162  -1.065  -1.375  1.00  0.00           H  
HETATM   30  H13 UNL     1       1.907  -2.361  -0.391  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.422  -0.600   0.574  1.00  0.00           H  
HETATM   32  H15 UNL     1       0.397  -1.859   1.510  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.674  -2.612   0.534  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.321  -3.588  -0.135  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.887  -2.986  -1.887  1.00  0.00           H  
HETATM   36  H19 UNL     1      -0.365  -2.128  -2.206  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.240  -0.587  -2.572  1.00  0.00           H  
HETATM   38  H21 UNL     1      -1.272  -0.052  -1.194  1.00  0.00           H  
HETATM   39  H22 UNL     1      -3.847  -1.726  -1.022  1.00  0.00           H  
HETATM   40  H23 UNL     1      -2.874  -0.982   0.368  1.00  0.00           H  
HETATM   41  H24 UNL     1      -4.211   0.692  -1.798  1.00  0.00           H  
HETATM   42  H25 UNL     1      -3.414   1.873   0.476  1.00  0.00           H  
HETATM   43  H26 UNL     1      -5.776  -0.448  -0.161  1.00  0.00           H  
HETATM   44  H27 UNL     1      -4.806   0.244   1.182  1.00  0.00           H  
HETATM   45  H28 UNL     1      -7.203   2.767   1.270  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   14   41
CONECT   13   42
CONECT   14   15   43   44
CONECT   15   16   16   17
CONECT   17   45
END

HMDB0061656
     RDKit          3D
3-Hydroxytetradecanoic acid
 45 44  0  0  0  0  0  0  0  0999 V2000
    6.2595    2.4077    0.7124 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5950    1.3658   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2727    1.0105    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5379   -0.0468   -0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2511   -0.3322    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4120   -1.3697   -0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1474   -1.5457    0.4825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7857   -2.5701   -0.1353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2177   -2.1722   -1.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9466   -0.8665   -1.5501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2093   -0.9035   -0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9221    0.4464   -0.7724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0125    1.4063   -0.2773 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1224    0.3982    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8483    1.6911    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4222    2.6184   -0.6305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9820    1.8725    0.8375 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7882    1.9166    1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4458    3.0301    1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8998    3.0927    0.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2561    0.4726   -0.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4837    1.7591   -1.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4950    0.6247    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6636    1.9270    0.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2129   -0.9446   -0.3431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4384    0.2605   -1.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6558    0.5936    0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -0.7242    1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619   -1.0645   -1.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -2.3607   -0.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4223   -0.5998    0.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3968   -1.8594    1.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6740   -2.6124    0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209   -3.5882   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8874   -2.9863   -1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649   -2.1276   -2.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2402   -0.5871   -2.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2720   -0.0520   -1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8470   -1.7259   -1.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737   -0.9815    0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2108    0.6918   -1.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4136    1.8735    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7758   -0.4484   -0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8057    0.2435    1.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2032    2.7666    1.2704 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
 12 14  1  0
 14 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  6
 13 42  1  0
 14 43  1  0
 14 44  1  0
 17 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-3-Hydroxymyristic acid	ChEBI
3S-Hydroxy-tetradecanoic acid	ChEBI
C14:0 3(S)-OH	ChEBI
C14:0 3-OH	ChEBI
L-beta-Hydroxymyristic acid	ChEBI
(S)-3-Hydroxymyristate	Generator
3S-Hydroxy-tetradecanoate	Generator
L-b-Hydroxymyristate	Generator
L-b-Hydroxymyristic acid	Generator
L-beta-Hydroxymyristate	Generator
L-Β-hydroxymyristate	Generator
L-Β-hydroxymyristic acid	Generator
3-Hydroxytetradecanoate	Generator
(S)-3-Hydroxytetradecanoate	HMDB
(3S)-3-Hydroxytetradecanoate	HMDB
(3S)-3-Hydroxytetradecanoic acid	HMDB
(3S)-Hydroxymyristate	HMDB
(3S)-Hydroxymyristic acid	HMDB
(S)-beta-Hydroxymyristate	HMDB
(S)-beta-Hydroxymyristic acid	HMDB
(S)-Β-hydroxymyristate	HMDB
(S)-Β-hydroxymyristic acid	HMDB
(±)-3-hydroxytetradecanoate	HMDB
(±)-3-hydroxytetradecanoic acid	HMDB
3-Hydroxymyristate	HMDB
3-Hydroxymyristic acid	HMDB
FA(14:0(3-OH))	HMDB
FA(14:0(3S-OH))	HMDB
S-3-Hydroxytetradecanoate	HMDB
S-3-Hydroxytetradecanoic acid	HMDB
beta-Hydroxymyristate	HMDB
beta-Hydroxymyristic acid	HMDB
beta-Hydroxytetradecanoate	HMDB
beta-Hydroxytetradecanoic acid	HMDB
Β-hydroxymyristate	HMDB
Β-hydroxymyristic acid	HMDB
Β-hydroxytetradecanoate	HMDB
Β-hydroxytetradecanoic acid	HMDB
3-Hydroxytetradecanoic acid	HMDB

Chemical Formula

C₁₄H₂₈O₃

Average Molecular Weight

244.375

Monoisotopic Molecular Weight

244.203844762

IUPAC Name

(3S)-3-hydroxytetradecanoic acid

Traditional Name

3-hydroxy-myristic acid

CAS Registry Number

35683-15-9

SMILES

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

InChI Identifier

InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)/t13-/m0/s1

InChI Key

ATRNZOYKSNPPBF-ZDUSSCGKSA-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
Beta-hydroxy acid
Hydroxy acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

3-hydroxy monocarboxylic acid (CHEBI:37374 )
hydroxy fatty acid (CHEBI:37374 )
Hydroxy fatty acids (LMFA01050323 )

Ontology

Not Available

Feces (PMID: 27275383)

Source

Exogenous

Exogenous (HMDB: HMDB0061656)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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	0.03 g/L	ALOGPS
logP	4.69	ALOGPS
logP	4.14	ChemAxon
logS	-3.9	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	12	ChemAxon
Refractivity	69.4 m³·mol⁻¹	ChemAxon
Polarizability	30.62 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]+	166.376	30932474
DeepCCS	[M-H]-	162.356	30932474
DeepCCS	[M-2H]-	199.809	30932474
DeepCCS	[M+Na]+	175.519	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]-	164.9	32859911
AllCCS	[M+Na-2H]-	165.9	32859911
AllCCS	[M+HCOO]-	167.2	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.	9.13 minutes	32390414
Predicted by Siyang on May 30, 2022	15.3515 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.7 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2461.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	361.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	177.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	190.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	430.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	690.0 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	646.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	106.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1396.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	484.7 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	1510.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	479.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	391.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	420.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	303.8 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	33.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxytetradecanoic acid	CCCCCCCCCCC[C@H](O)CC(O)=O	3043.7	Standard polar	33892256
3-Hydroxytetradecanoic acid	CCCCCCCCCCC[C@H](O)CC(O)=O	1864.5	Standard non polar	33892256
3-Hydroxytetradecanoic acid	CCCCCCCCCCC[C@H](O)CC(O)=O	1974.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxytetradecanoic acid,1TMS,isomer #1	CCCCCCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C	1982.4	Semi standard non polar	33892256
3-Hydroxytetradecanoic acid,1TMS,isomer #2	CCCCCCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C	1965.6	Semi standard non polar	33892256
3-Hydroxytetradecanoic acid,2TMS,isomer #1	CCCCCCCCCCC[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2052.4	Semi standard non polar	33892256
3-Hydroxytetradecanoic acid,1TBDMS,isomer #1	CCCCCCCCCCC[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C	2217.4	Semi standard non polar	33892256
3-Hydroxytetradecanoic acid,1TBDMS,isomer #2	CCCCCCCCCCC[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C	2208.6	Semi standard non polar	33892256
3-Hydroxytetradecanoic acid,2TBDMS,isomer #1	CCCCCCCCCCC[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2514.3	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-Hydroxytetradecanoic acid GC-MS (2 TMS)	splash10-001i-4961000000-5528c5db71884cb54509	2019-10-24	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Hydroxytetradecanoic acid GC-EI-TOF (Non-derivatized)	splash10-0002-1920000000-4232a13b15fd6bcda6d4	2019-10-24	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxytetradecanoic 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 - 3-Hydroxytetradecanoic acid 10V, Positive-QTOF	splash10-0002-7490000000-e411730b6954cd86436e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanoic acid 20V, Positive-QTOF	splash10-0ab9-9200000000-b7e85c97d8487c52e8cc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanoic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-0525dd3ff78d95a6db8e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanoic acid 10V, Negative-QTOF	splash10-052f-7090000000-d25b3956d871bbed563c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanoic acid 20V, Negative-QTOF	splash10-0a4i-9000000000-a79b5cb90536466a51ca	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytetradecanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-20ac637addcc98814c6d	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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	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	27275383	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4472294

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5312869

PDB ID

Not Available

ChEBI ID

37374

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
The AOCS Lipid Library [Link]

Showing metabocard for 3-Hydroxytetradecanoic acid (HMDB0061656)

MOL for HMDB0061656 (3-Hydroxytetradecanoic acid)

3D MOL for HMDB0061656 (3-Hydroxytetradecanoic acid)

3D SDF for HMDB0061656 (3-Hydroxytetradecanoic acid)

3D-SDF for HMDB0061656 (3-Hydroxytetradecanoic acid)

PDB for HMDB0061656 (3-Hydroxytetradecanoic acid)

3D PDB for HMDB0061656 (3-Hydroxytetradecanoic acid)

SMILES for HMDB0061656 (3-Hydroxytetradecanoic acid)

INCHI for HMDB0061656 (3-Hydroxytetradecanoic acid)

Structure for HMDB0061656 (3-Hydroxytetradecanoic acid)

3D Structure for HMDB0061656 (3-Hydroxytetradecanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra