NP-MRD: Showing NP-Card for 2-Hydroxydecanedioic acid (NP0000606)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:16:50 UTC

NP-MRD ID

NP0000606

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-Hydroxydecanedioic acid

Description

2-Hydroxydecanedioic acid appears in the urine of children affected with peroxisomal disorders such as urines of children with neonatal adrenoleukodystrophy and Zellweger syndrome and is a useful marker for these diseases. (PMID 2943344 ).

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>
NP0000606

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

218.2469 Da

Monoisotopic Mass

218.11542 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Solanum tuberosum	KNApSAcK Database	22123792
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000424

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
Yu H, Gild P, Pompe RS, Vetterlein MW, Ludwig TA, Soave A, Kolker M, Maurer V, Marks P, Becker A, Punke MA, Fisch M, Rink M, Dahlem R, Meyer CP: Anesthetic Technique (Spinal vs. General Anesthesia) in Holmium Laser Enucleation of the Prostate: Retrospective Analysis of Procedural and Functional Outcomes among 1,159 Patients. Urol Int. 2021 Aug 17:1-8. doi: 10.1159/000517542. [PubMed:34404060 ]
Al Riyees L, Al Madani W, Firwana N, Balkhy HH, Ferwana M, Alkhudhayri A: Antibiotic Prophylaxis against Surgical Site Infection after Open Hernia Surgery: A Systematic Review and Meta-Analysis. Eur Surg Res. 2021 Aug 17:1-13. doi: 10.1159/000517404. [PubMed:34404046 ]
Geer MJ, Foucar CE, Devata S, Benitez L, Perissinotti AJ, Marini BL, Bixby D: Clinical Availability of ATRA for Patients With Suspected Acute Promyelocytic Leukemia: Why Guidelines May Not Be Followed. J Natl Compr Canc Netw. 2021 Aug 17. pii: jnccn20455. doi: 10.6004/jnccn.2021.7013. [PubMed:34404029 ]

Showing NP-Card for 2-Hydroxydecanedioic acid (NP0000606)

MOL for NP0000606 (2-Hydroxydecanedioic acid)

3D MOL for NP0000606 (2-Hydroxydecanedioic acid)

3D SDF for NP0000606 (2-Hydroxydecanedioic acid)

3D-SDF for NP0000606 (2-Hydroxydecanedioic acid)

PDB for NP0000606 (2-Hydroxydecanedioic acid)

3D PDB for NP0000606 (2-Hydroxydecanedioic acid)

SMILES for NP0000606 (2-Hydroxydecanedioic acid)

INCHI for NP0000606 (2-Hydroxydecanedioic acid)

Structure for NP0000606 (2-Hydroxydecanedioic acid)

3D Structure for NP0000606 (2-Hydroxydecanedioic acid)