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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:34 UTC

Update Date

2022-03-07 02:49:12 UTC

HMDB ID

HMDB0002059

Secondary Accession Numbers

HMDB02059

Metabolite Identification

Common Name

12-Hydroxydodecanoic acid

Description

12-hydroxydodecanoic acid is the substrate of the human glutathione-dependent formaldehyde dehydrogenase (EC1.1.1.1). The enzyme that catalyzes the conversion of alcohols to aldehydes is a zinc-containing dimeric enzyme responsible for the oxidation of long-chain alcohols and omega-hydroxy fatty acids. (OMIM). The human glutathione-dependent formaldehyde dehydrogenase is unique among the structurally studied members of the alcohol dehydrogenase family in that it follows a random bi kinetic mechanism forming a binary complex, and a ternary complex with NAD+. (PMID 12196016 ).

Structure

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

HMDB0002059
     RDKit          3D
12-Hydroxydodecanoic acid
 39 38  0  0  0  0  0  0  0  0999 V2000
    5.5727    1.1603   -1.2575 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599    0.3532   -0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1960    0.3865    0.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789   -0.6177    0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544   -0.6097   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8737    0.7001    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4687    0.6495   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690   -0.3971    0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7631   -0.3250   -0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5467   -1.3562    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462   -1.6168   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0004   -0.6025    0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283    0.6817   -0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1871    1.5369   -0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2715    1.7964    1.0522 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5984    1.2790    0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9880   -0.4268    1.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740   -1.6595    0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5484   -0.9486   -1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0270   -1.3950    0.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919    1.5017   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9142    1.0168    1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4391    0.4615   -1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9419    1.6249   -0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0665   -1.4083    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6218   -0.1830    1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778   -0.5705   -1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211    0.7146   -0.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9724   -2.3382    0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792   -1.1895    1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539   -2.1416   -1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -2.4871    0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1455   -0.4498    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9682   -1.1056   -0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8779    0.5306   -1.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1180    1.3104   -0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0884    2.4813   -0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0721    0.9906   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7078    2.6526    1.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
M  END

12H
  Mrv1652305261923522D          

 15 14  0  0  0  0            999 V2000
   -3.7259    0.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0113   -0.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2969    0.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5823   -0.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8678    0.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1533   -0.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5612    0.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2758   -0.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9903    0.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7048   -0.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4194    0.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339   -0.1851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404   -0.1851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8484    0.2274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1339   -1.0102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  2  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002059

> <DATABASE_NAME>
hmdb

> <SMILES>
OCCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H24O3/c13-11-9-7-5-3-1-2-4-6-8-10-12(14)15/h13H,1-11H2,(H,14,15)

> <INCHI_KEY>
ZDHCZVWCTKTBRY-UHFFFAOYSA-N

> <FORMULA>
C12H24O3

> <MOLECULAR_WEIGHT>
216.3172

> <EXACT_MASS>
216.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.84877088275522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-hydroxydodecanoic acid

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
3.041629501

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.84394282199214

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952019704603348

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9922594590354228

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
60.6083

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-hydroxydodecanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002059
     RDKit          3D
12-Hydroxydodecanoic acid
 39 38  0  0  0  0  0  0  0  0999 V2000
    5.5727    1.1603   -1.2575 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599    0.3532   -0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1960    0.3865    0.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789   -0.6177    0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544   -0.6097   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8737    0.7001    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4687    0.6495   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690   -0.3971    0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7631   -0.3250   -0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5467   -1.3562    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462   -1.6168   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0004   -0.6025    0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283    0.6817   -0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1871    1.5369   -0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2715    1.7964    1.0522 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5984    1.2790    0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9880   -0.4268    1.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740   -1.6595    0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5484   -0.9486   -1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0270   -1.3950    0.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919    1.5017   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9142    1.0168    1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4391    0.4615   -1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9419    1.6249   -0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0665   -1.4083    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6218   -0.1830    1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778   -0.5705   -1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211    0.7146   -0.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9724   -2.3382    0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792   -1.1895    1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539   -2.1416   -1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -2.4871    0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1455   -0.4498    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9682   -1.1056   -0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8779    0.5306   -1.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1180    1.3104   -0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0884    2.4813   -0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0721    0.9906   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7078    2.6526    1.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 12H                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -6.955   0.424   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.621  -0.346   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.288   0.424   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.954  -0.346   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.620   0.424   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.286  -0.346   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.048   0.424   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.381  -0.346   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.715   0.424   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.049  -0.346   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.383   0.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.717  -0.346   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -8.289  -0.346   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.050   0.424   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       7.717  -1.886   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   14   15                                                  
CONECT   13    1                                                            
CONECT   14   12                                                            
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0002059
HETATM    1  O1  UNL     1       5.573   1.160  -1.257  1.00  0.00           O  
HETATM    2  C1  UNL     1       5.860   0.353  -0.357  1.00  0.00           C  
HETATM    3  O2  UNL     1       7.196   0.386   0.085  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.979  -0.618   0.291  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.554  -0.610  -0.195  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.874   0.700   0.021  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.469   0.649  -0.490  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.669  -0.397   0.210  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.763  -0.325  -0.409  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.547  -1.356   0.282  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.946  -1.617  -0.055  1.00  0.00           C  
HETATM   12  C10 UNL     1      -4.000  -0.603   0.126  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.928   0.682  -0.602  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.187   1.537  -0.294  1.00  0.00           C  
HETATM   15  O3  UNL     1      -5.271   1.796   1.052  1.00  0.00           O  
HETATM   16  H1  UNL     1       7.598   1.279   0.266  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.988  -0.427   1.383  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.374  -1.659   0.116  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.548  -0.949  -1.236  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.027  -1.395   0.392  1.00  0.00           H  
HETATM   21  H6  UNL     1       3.392   1.502  -0.578  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.914   1.017   1.092  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.439   0.462  -1.597  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.942   1.625  -0.359  1.00  0.00           H  
HETATM   25  H10 UNL     1       1.066  -1.408   0.048  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.622  -0.183   1.278  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.678  -0.570  -1.491  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.021   0.715  -0.320  1.00  0.00           H  
HETATM   29  H14 UNL     1      -0.972  -2.338   0.137  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.479  -1.190   1.397  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.054  -2.142  -1.066  1.00  0.00           H  
HETATM   32  H17 UNL     1      -3.259  -2.487   0.636  1.00  0.00           H  
HETATM   33  H18 UNL     1      -4.145  -0.450   1.235  1.00  0.00           H  
HETATM   34  H19 UNL     1      -4.968  -1.106  -0.226  1.00  0.00           H  
HETATM   35  H20 UNL     1      -3.878   0.531  -1.678  1.00  0.00           H  
HETATM   36  H21 UNL     1      -3.118   1.310  -0.167  1.00  0.00           H  
HETATM   37  H22 UNL     1      -5.088   2.481  -0.860  1.00  0.00           H  
HETATM   38  H23 UNL     1      -6.072   0.991  -0.667  1.00  0.00           H  
HETATM   39  H24 UNL     1      -5.708   2.653   1.263  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5   17   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8   23   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   39
END

HMDB0002059
     RDKit          3D
12-Hydroxydodecanoic acid
 39 38  0  0  0  0  0  0  0  0999 V2000
    5.5727    1.1603   -1.2575 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599    0.3532   -0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1960    0.3865    0.0854 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789   -0.6177    0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544   -0.6097   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8737    0.7001    0.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4687    0.6495   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690   -0.3971    0.2105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7631   -0.3250   -0.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5467   -1.3562    0.2821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462   -1.6168   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0004   -0.6025    0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283    0.6817   -0.6022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1871    1.5369   -0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2715    1.7964    1.0522 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5984    1.2790    0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9880   -0.4268    1.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3740   -1.6595    0.1159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5484   -0.9486   -1.2364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0270   -1.3950    0.3922 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3919    1.5017   -0.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9142    1.0168    1.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4391    0.4615   -1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9419    1.6249   -0.3589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0665   -1.4083    0.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6218   -0.1830    1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778   -0.5705   -1.4907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0211    0.7146   -0.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9724   -2.3382    0.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792   -1.1895    1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539   -2.1416   -1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2589   -2.4871    0.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1455   -0.4498    1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9682   -1.1056   -0.2260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8779    0.5306   -1.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1180    1.3104   -0.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0884    2.4813   -0.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0721    0.9906   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7078    2.6526    1.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12-Hydroxy lauric acid	ChEBI
2-Hydroxy-dodecanoic acid	ChEBI
Omega-hydroxy lauric acid	ChEBI
Omega-hydroxydodecanoic acid	ChEBI
Omega-OH dodecanoic acid	ChEBI
Omega-OH lauric acid	ChEBI
12-Hydroxy laate	Generator
12-Hydroxy laic acid	Generator
2-Hydroxy-dodecanoate	Generator
Omega-hydroxy laate	Generator
Omega-hydroxy laic acid	Generator
Omega-hydroxydodecanoate	Generator
Omega-OH dodecanoate	Generator
Omega-OH laate	Generator
Omega-OH laic acid	Generator
12-Hydroxydodecanoate	Generator
12-Hydroxylaurate	HMDB
12-Hydroxylauric acid	HMDB, MeSH
Omega hydroxy dodecanoate	HMDB
Omega hydroxy dodecanoic acid	HMDB
Omega-hydroxylauric acid	MeSH, HMDB
12-Hydroxydodecanoic acid	ChEBI
Sabinate	Generator, HMDB

Chemical Formula

C₁₂H₂₄O₃

Average Molecular Weight

216.3172

Monoisotopic Molecular Weight

216.172544634

IUPAC Name

12-hydroxydodecanoic acid

Traditional Name

12-hydroxydodecanoic acid

CAS Registry Number

505-95-3

SMILES

OCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C12H24O3/c13-11-9-7-5-3-1-2-4-6-8-10-12(14)15/h13H,1-11H2,(H,14,15)

InChI Key

ZDHCZVWCTKTBRY-UHFFFAOYSA-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
Hydroxy fatty acid
Straight chain fatty acid
Fatty acyl
Fatty acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:39567 )
omega-hydroxy fatty acid (CHEBI:39567 )
Hydroxy fatty acids (C08317 )
Hydroxy fatty acids (LMFA01050039 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0002059)

Food

Food (HMDB: HMDB0002059)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002059)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0002059)

Role

Biological role

Energy source (HMDB: HMDB0002059)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002059)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002059)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	85.00 to 88.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	359.00 to 360.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	278 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.866 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	152.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00002077

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	3.5	ALOGPS
logP	3.04	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-2	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	11	ChemAxon
Refractivity	60.61 m³·mol⁻¹	ChemAxon
Polarizability	26.85 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.59	31661259
DarkChem	[M-H]-	151.574	31661259
DeepCCS	[M+H]+	151.516	30932474
DeepCCS	[M-H]-	147.492	30932474
DeepCCS	[M-2H]-	184.758	30932474
DeepCCS	[M+Na]+	160.444	30932474
AllCCS	[M+H]+	152.1	32859911
AllCCS	[M+H-H2O]+	148.6	32859911
AllCCS	[M+NH4]+	155.3	32859911
AllCCS	[M+Na]+	156.2	32859911
AllCCS	[M-H]-	155.8	32859911
AllCCS	[M+Na-2H]-	156.9	32859911
AllCCS	[M+HCOO]-	158.1	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.	7.61 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5492 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.08 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2140.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	373.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	476.1 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	496.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	136.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1158.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	401.4 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	1260.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	336.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	406.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	262.5 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	117.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
12-Hydroxydodecanoic acid	OCCCCCCCCCCCC(O)=O	2947.9	Standard polar	33892256
12-Hydroxydodecanoic acid	OCCCCCCCCCCCC(O)=O	1781.2	Standard non polar	33892256
12-Hydroxydodecanoic acid	OCCCCCCCCCCCC(O)=O	1868.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
12-Hydroxydodecanoic acid,1TMS,isomer #1	C[Si](C)(C)OCCCCCCCCCCCC(=O)O	1948.5	Semi standard non polar	33892256
12-Hydroxydodecanoic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)CCCCCCCCCCCO	1908.6	Semi standard non polar	33892256
12-Hydroxydodecanoic acid,2TMS,isomer #1	C[Si](C)(C)OCCCCCCCCCCCC(=O)O[Si](C)(C)C	2010.2	Semi standard non polar	33892256
12-Hydroxydodecanoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCCCCCCCCC(=O)O	2179.0	Semi standard non polar	33892256
12-Hydroxydodecanoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCO	2151.7	Semi standard non polar	33892256
12-Hydroxydodecanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2489.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 12-Hydroxydodecanoic acid EI-B (Non-derivatized)	splash10-053v-9100000000-a92cb682b3bdad87a6b8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 12-Hydroxydodecanoic acid EI-B (Non-derivatized)	splash10-000t-9600000000-80739833ebc1d91a8f41	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 12-Hydroxydodecanoic acid EI-B (Non-derivatized)	splash10-053v-9100000000-a92cb682b3bdad87a6b8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 12-Hydroxydodecanoic acid EI-B (Non-derivatized)	splash10-000t-9600000000-80739833ebc1d91a8f41	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Hydroxydodecanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-8900000000-cca19c514cbd27e8ceb0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Hydroxydodecanoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9661000000-4b85552e5625e377c6ba	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 12-Hydroxydodecanoic 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 - 12-Hydroxydodecanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014i-1790000000-86939bdc2617444c9391	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Negative-QTOF	splash10-052f-9200000000-897a99eb6e667c5ecef1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Negative-QTOF	splash10-014i-0090000000-bf2f637495ab7368ab08	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Positive-QTOF	splash10-001i-9500000000-8b9aea66eb0e0ded6c6b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Positive-QTOF	splash10-052f-9000000000-9dcbfcf4beef873ee06a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Negative-QTOF	splash10-014i-0190000000-472d75ec2602139f5cc6	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Positive-QTOF	splash10-0a59-9200000000-6ad7fc879c5d723218a0	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Positive-QTOF	splash10-0002-0910000000-844a5190b2e310ec626f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Positive-QTOF	splash10-000t-1900000000-499d158a0890694b2f7d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Positive-QTOF	splash10-07gv-9600000000-cc905025c302321c2c33	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Negative-QTOF	splash10-014i-0790000000-ba75e81dad07b4533bfa	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Negative-QTOF	splash10-00kb-1920000000-64041ca2f1e9970c6e5e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Negative-QTOF	splash10-0a4m-9600000000-2c68993598743f556da6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Negative-QTOF	splash10-014i-0190000000-9d7bab7f261095aca280	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Negative-QTOF	splash10-014j-2890000000-c7f539a275c9a02bb82b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Negative-QTOF	splash10-002f-9400000000-276cebbd2318c8b4ae1d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Positive-QTOF	splash10-0671-9410000000-b1c59c70e8e4ae8d9b2f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Positive-QTOF	splash10-0avi-9100000000-b3eb89584383f4392851	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-c3285b34ced442e30df5	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03704

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6465

PubChem Compound

79034

PDB ID

Not Available

ChEBI ID

39567

Food Biomarker Ontology

Not Available

VMH ID

WHDDCA

MarkerDB ID

Not Available

Good Scents ID

rw1157251

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sanghani PC, Robinson H, Bosron WF, Hurley TD: Human glutathione-dependent formaldehyde dehydrogenase. Structures of apo, binary, and inhibitory ternary complexes. Biochemistry. 2002 Sep 3;41(35):10778-86. [PubMed:12196016 ]

Showing metabocard for 12-Hydroxydodecanoic acid (HMDB0002059)

MOL for HMDB0002059 (12-Hydroxydodecanoic acid)

3D MOL for HMDB0002059 (12-Hydroxydodecanoic acid)

3D SDF for HMDB0002059 (12-Hydroxydodecanoic acid)

3D-SDF for HMDB0002059 (12-Hydroxydodecanoic acid)

PDB for HMDB0002059 (12-Hydroxydodecanoic acid)

3D PDB for HMDB0002059 (12-Hydroxydodecanoic acid)

SMILES for HMDB0002059 (12-Hydroxydodecanoic acid)

INCHI for HMDB0002059 (12-Hydroxydodecanoic acid)

Structure for HMDB0002059 (12-Hydroxydodecanoic acid)

3D Structure for HMDB0002059 (12-Hydroxydodecanoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra