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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:20:01 UTC

HMDB ID

HMDB0000424

Secondary Accession Numbers

HMDB00424

Metabolite Identification

Common Name

2-Hydroxydecanedioic acid

Description

2-Hydroxydecanedioic acid, also known as a-hydroxysebasate or 2-hydroxysebacic acid, 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. 2-Hydroxydecanedioic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2-hydroxydecanedioic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-Hydroxydecanedioic acid.

Structure

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

HMDB0000424
     RDKit          3D
2-Hydroxydecanedioic acid
 33 32  0  0  0  0  0  0  0  0999 V2000
    5.1030   -0.1338    1.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3446    0.0792    0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051   -0.2658   -1.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0264    0.7200    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2648    0.8877   -0.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9194    1.5435   -0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    0.7211    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1823   -0.6414   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.5270    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3491   -1.2107    0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4803   -0.9575    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6316   -0.7351    0.9069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748    0.3318   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0768    1.3316   -0.2706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    0.6124   -1.7656 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4512   -0.9534   -1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623    0.0645    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1776    1.7388    0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8895    1.5539   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708   -0.0616   -1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    1.6326   -1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645    2.5792   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817    1.2798    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    0.6356    1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3510   -0.5622   -1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822   -1.1251   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983   -2.5901    0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941   -1.7152    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -0.3634    1.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914   -2.0728    1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7966   -1.7974   -0.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3234   -0.4055    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9943    1.4063   -1.8754 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
 11 13  1  0
 13 14  2  0
 13 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
 12 32  1  0
 15 33  1  0
M  END

2-Hydroxydecanedioic acid.mol
  Mrv1652305261923542D          

 15 14  0  0  0  0            999 V2000
    3.2083    0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5023   -0.1668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7845    0.2399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557    0.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3550   -0.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0732    0.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7838   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5021    0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2127   -0.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2121    1.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9310   -0.1377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2051   -1.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9310    0.1871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5050   -1.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  1 11  2  0  0  0  0
  1 12  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000424

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(CCCCCCCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O5/c11-8(10(14)15)6-4-2-1-3-5-7-9(12)13/h8,11H,1-7H2,(H,12,13)(H,14,15)

> <INCHI_KEY>
LPIOYESQKJFWPQ-UHFFFAOYSA-N

> <FORMULA>
C10H18O5

> <MOLECULAR_WEIGHT>
218.2469

> <EXACT_MASS>
218.115423686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.383498888262327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxydecanedioic acid

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
1.3978631019999996

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.834206020743932

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.15977916410913

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7975287125165815

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
52.6352

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxysebacic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000424
     RDKit          3D
2-Hydroxydecanedioic acid
 33 32  0  0  0  0  0  0  0  0999 V2000
    5.1030   -0.1338    1.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3446    0.0792    0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051   -0.2658   -1.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0264    0.7200    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2648    0.8877   -0.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9194    1.5435   -0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    0.7211    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1823   -0.6414   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.5270    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3491   -1.2107    0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4803   -0.9575    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6316   -0.7351    0.9069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748    0.3318   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0768    1.3316   -0.2706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    0.6124   -1.7656 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4512   -0.9534   -1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623    0.0645    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1776    1.7388    0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8895    1.5539   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708   -0.0616   -1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    1.6326   -1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645    2.5792   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817    1.2798    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    0.6356    1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3510   -0.5622   -1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822   -1.1251   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983   -2.5901    0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941   -1.7152    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -0.3634    1.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914   -2.0728    1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7966   -1.7974   -0.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3234   -0.4055    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9943    1.4063   -1.8754 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
 11 13  1  0
 13 14  2  0
 13 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
 12 32  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2-Hydroxydecanedioic acid.mol                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       5.989   0.486   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.671  -0.311   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.331   0.448   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.005  -0.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.664   0.423   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.663  -0.359   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.003   0.399   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.330  -0.384   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.671   0.374   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.997  -0.408   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.996   2.295   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.338  -0.257   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.983  -2.295   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -7.338   0.349   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.676  -1.901   0.000  0.00  0.00           O+0
CONECT    1    2   11   12                                                  
CONECT    2    1    3   15                                                  
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   13   14                                                  
CONECT   11    1                                                            
CONECT   12    1                                                            
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15    2                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0000424
HETATM    1  O1  UNL     1       5.103  -0.134   1.154  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.345   0.079   0.175  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.705  -0.266  -1.111  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.026   0.720   0.418  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.265   0.888  -0.897  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.919   1.543  -0.647  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.064   0.721   0.283  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.182  -0.641  -0.312  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.008  -1.527   0.514  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.349  -1.211   0.948  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.480  -0.958   0.040  1.00  0.00           C  
HETATM   12  O3  UNL     1      -4.632  -0.735   0.907  1.00  0.00           O  
HETATM   13  C10 UNL     1      -3.375   0.332  -0.674  1.00  0.00           C  
HETATM   14  O4  UNL     1      -4.077   1.332  -0.271  1.00  0.00           O  
HETATM   15  O5  UNL     1      -2.591   0.612  -1.766  1.00  0.00           O  
HETATM   16  H1  UNL     1       5.451  -0.953  -1.256  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.462   0.064   1.113  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.178   1.739   0.832  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.889   1.554  -1.526  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.171  -0.062  -1.442  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.394   1.633  -1.618  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.065   2.579  -0.282  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.882   1.280   0.426  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.517   0.636   1.296  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.351  -0.562  -1.372  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.882  -1.125  -0.273  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.998  -2.590   0.073  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.394  -1.715   1.469  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.311  -0.363   1.718  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.691  -2.073   1.628  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.797  -1.797  -0.581  1.00  0.00           H  
HETATM   32  H17 UNL     1      -4.323  -0.406   1.767  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.994   1.406  -1.875  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   13   31
CONECT   12   32
CONECT   13   14   14   15
CONECT   15   33
END

HMDB0000424
     RDKit          3D
2-Hydroxydecanedioic acid
 33 32  0  0  0  0  0  0  0  0999 V2000
    5.1030   -0.1338    1.1541 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3446    0.0792    0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7051   -0.2658   -1.1113 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0264    0.7200    0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2648    0.8877   -0.8966 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9194    1.5435   -0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    0.7211    0.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1823   -0.6414   -0.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.5270    0.5141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3491   -1.2107    0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4803   -0.9575    0.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6316   -0.7351    0.9069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748    0.3318   -0.6743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0768    1.3316   -0.2706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5913    0.6124   -1.7656 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4512   -0.9534   -1.2559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4623    0.0645    1.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1776    1.7388    0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8895    1.5539   -1.5260 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1708   -0.0616   -1.4418 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    1.6326   -1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645    2.5792   -0.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8817    1.2798    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    0.6356    1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3510   -0.5622   -1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8822   -1.1251   -0.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9983   -2.5901    0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941   -1.7152    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3113   -0.3634    1.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6914   -2.0728    1.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7966   -1.7974   -0.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3234   -0.4055    1.7668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9943    1.4063   -1.8754 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
 11 13  1  0
 13 14  2  0
 13 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
 12 32  1  0
 15 33  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Hydroxydecanedioate	Generator
2-Hydroxy-decandioate	HMDB
2-Hydroxy-decandioic acid	HMDB
2-Hydroxysebacate	HMDB
2-Hydroxysebacic acid	HMDB
a-Hydroxysebasate	HMDB
a-Hydroxysebasic acid	HMDB
alpha-Hydroxysebasate	HMDB
alpha-Hydroxysebasic acid	HMDB
2-Hydroxy-decanedioate	HMDB

Chemical Formula

C₁₀H₁₈O₅

Average Molecular Weight

218.2469

Monoisotopic Molecular Weight

218.115423686

IUPAC Name

2-hydroxydecanedioic acid

Traditional Name

2-hydroxysebacic acid

CAS Registry Number

103963-71-9

SMILES

OC(CCCCCCCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H18O5/c11-8(10(14)15)6-4-2-1-3-5-7-9(12)13/h8,11H,1-7H2,(H,12,13)(H,14,15)

InChI Key

LPIOYESQKJFWPQ-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
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Monosaccharide
Fatty acid
Fatty acyl
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Dicarboxylic acids (LMFA01170076 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118 - 121 °C	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	2.42 g/L	ALOGPS
logP	0.87	ALOGPS
logP	1.4	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	52.64 m³·mol⁻¹	ChemAxon
Polarizability	23.38 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]+	151.452	31661259
DarkChem	[M-H]-	147.537	31661259
AllCCS	[M+H]+	150.051	32859911
AllCCS	[M-H]-	149.743	32859911
DeepCCS	[M+H]+	148.858	30932474
DeepCCS	[M-H]-	144.834	30932474
DeepCCS	[M-2H]-	182.518	30932474
DeepCCS	[M+Na]+	158.183	30932474
AllCCS	[M+H]+	150.1	32859911
AllCCS	[M+H-H2O]+	146.5	32859911
AllCCS	[M+NH4]+	153.3	32859911
AllCCS	[M+Na]+	154.3	32859911
AllCCS	[M-H]-	149.7	32859911
AllCCS	[M+Na-2H]-	150.6	32859911
AllCCS	[M+HCOO]-	151.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxydecanedioic acid	OC(CCCCCCCC(O)=O)C(O)=O	2951.3	Standard polar	33892256
2-Hydroxydecanedioic acid	OC(CCCCCCCC(O)=O)C(O)=O	1598.7	Standard non polar	33892256
2-Hydroxydecanedioic acid	OC(CCCCCCCC(O)=O)C(O)=O	1894.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Hydroxydecanedioic acid,1TMS,isomer #1	C[Si](C)(C)OC(CCCCCCCC(=O)O)C(=O)O	1928.5	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)CCCCCCCC(O)C(=O)O	1912.2	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,1TMS,isomer #3	C[Si](C)(C)OC(=O)C(O)CCCCCCCC(=O)O	1908.9	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C)C(=O)O	1984.8	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(CCCCCCCC(=O)O)O[Si](C)(C)C	1948.2	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)CCCCCCCC(O)C(=O)O[Si](C)(C)C	1975.2	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2047.3	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CCCCCCCC(=O)O)C(=O)O	2186.2	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O)C(=O)O	2157.1	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(O)CCCCCCCC(=O)O	2173.9	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C(C)(C)C)C(=O)O	2476.4	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C	2457.5	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O)C(=O)O[Si](C)(C)C(C)(C)C	2462.8	Semi standard non polar	33892256
2-Hydroxydecanedioic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2707.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9710000000-5fe9b8e6d318d5edf2e9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (3 TMS) - 70eV, Positive	splash10-016r-7649300000-ef73b5c677459a4e4032	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Hydroxydecanedioic acid GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 10V, Positive-QTOF	splash10-0uyi-0890000000-b8439c284ac682367d51	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 20V, Positive-QTOF	splash10-0kh9-2920000000-3620dca641969f0dd8a2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 40V, Positive-QTOF	splash10-0a7m-9300000000-e8753077d260110272f2	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 10V, Negative-QTOF	splash10-014i-1790000000-de7ab953c1ff73d7dc41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 20V, Negative-QTOF	splash10-00di-1910000000-80317878d8a89b878c50	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 40V, Negative-QTOF	splash10-0a6r-9600000000-7364e1a98ebf40595428	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 10V, Positive-QTOF	splash10-0uxr-2970000000-19a5a07acdba79f72a65	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 20V, Positive-QTOF	splash10-053r-9200000000-15c7825b2a6fd1e91d48	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 40V, Positive-QTOF	splash10-0a4i-9000000000-6eef4b232bf26f42a6a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 10V, Negative-QTOF	splash10-014i-0290000000-40841675c8e6ee707caf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 20V, Negative-QTOF	splash10-06dj-2920000000-6703bfa04e1a83a7ea8a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Hydroxydecanedioic acid 40V, Negative-QTOF	splash10-0a4l-9100000000-0ee8ff6b7d6aeed7288e	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.39-0.67 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	0.37-0.55 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Available	Not Available	Peroxisomal diseases	11978597	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022037

KNApSAcK ID

C00055623

Chemspider ID

113866

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5413

PubChem Compound

128458

PDB ID

Not Available

ChEBI ID

89312

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Chiruta, Chandramouli; Jachak, Santosh; Clive, Derrick L. J. A convenient general method for the synthesis of hydroxy diacids. Tetrahedron Letters (2007), 48(18), 3141-3143.

Material Safety Data Sheet (MSDS)

Not Available

General References

Rocchiccioli F, Cartier PH, Aubourg P, Bougneres PF: Mass spectrometric identification of 2-hydroxy-sebacic acid in the urines of patients with neonatal adrenoleukodystrophy and Zellweger syndrome. Biomed Environ Mass Spectrom. 1986 Jun;13(6):315-8. [PubMed:2943344 ]
Kajita M, Iwase K, Matsumoto M, Kuhara T, Sinka T, Matsumoto I: [Clinical and biochemical studies in a case of acute encephalopathy associated with calcium hopanthenate administration]. No To Hattatsu. 1990 May;22(3):267-73. [PubMed:2194543 ]
Muth A, Jung J, Bilke S, Scharrer A, Mosandl A, Sewell AC, Bohles H: Simultaneous enantioselective analysis of chiral urinary metabolites in patients with Zellweger syndrome. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 25;792(2):269-77. [PubMed:12860034 ]
Muth A, Mosandl A, Wanders RJ, Nowaczyk MJ, Baric I, Bohles H, Sewell AC: Stereoselective analysis of 2-hydroxysebacic acid in urine of patients with Zellweger syndrome and of premature infants fed with medium-chain triglycerides. J Inherit Metab Dis. 2003;26(6):583-92. [PubMed:14605504 ]

Showing metabocard for 2-Hydroxydecanedioic acid (HMDB0000424)

MOL for HMDB0000424 (2-Hydroxydecanedioic acid)

3D MOL for HMDB0000424 (2-Hydroxydecanedioic acid)

3D SDF for HMDB0000424 (2-Hydroxydecanedioic acid)

3D-SDF for HMDB0000424 (2-Hydroxydecanedioic acid)

PDB for HMDB0000424 (2-Hydroxydecanedioic acid)

3D PDB for HMDB0000424 (2-Hydroxydecanedioic acid)

SMILES for HMDB0000424 (2-Hydroxydecanedioic acid)

INCHI for HMDB0000424 (2-Hydroxydecanedioic acid)

Structure for HMDB0000424 (2-Hydroxydecanedioic acid)

3D Structure for HMDB0000424 (2-Hydroxydecanedioic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra