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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-09-22 17:43:45 UTC

HMDB ID

HMDB0000872

Secondary Accession Numbers

HMDB00872

Metabolite Identification

Common Name

Tetradecanedioic acid

Description

Tetradecanedioic acid, also known as 1,14-tetradecanedioate or NSC 9504, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Tetradecanedioic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

Structure

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

HMDB0000872
     RDKit          3D
Tetradecanedioic acid
 44 43  0  0  0  0  0  0  0  0999 V2000
    5.9392   -1.7601    1.5377 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3890   -1.5516    0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7906   -1.6029    0.2157 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4902   -1.2669   -0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0714   -1.1112   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9216    0.0482    0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5131    0.2722    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351    0.5188    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1572    0.7319    0.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8732    0.9853   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2207    1.1901    0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904    1.4477   -0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5867    1.6370   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1178    0.5464    0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4537   -0.7538    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4035   -1.5200   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3200   -1.6618   -1.8628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4109   -2.1522    0.1301 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3931   -0.9205    0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8030   -0.2492   -1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5882   -2.0086   -1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -2.0763    0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720   -0.9924   -1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5509   -0.0571    1.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2953    0.9542    0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743   -0.5998    1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    1.1566    1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4699   -0.4195   -0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893    1.3559   -0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -0.1446    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1368    1.5940    1.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892    0.1777   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5691    1.9337   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530    0.3126    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1192    2.1141    0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0398    2.4296   -1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2191    0.7030   -1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3828    1.9732   -0.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4618    2.5584    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670    0.3563    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0764    0.9265    1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3086   -0.5985   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8528   -1.4045    0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0696   -3.0715   -0.1013 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
 15 16  1  0
 16 17  2  0
 16 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 18 44  1  0
M  END

Tetrahydro-11-deoxycorticosterone.mol
  Mrv1652305271900302D          

 18 17  0  0  0  0            999 V2000
    4.2868    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.8250    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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  1 15  2  0  0  0  0
  1 16  1  0  0  0  0
 14 17  2  0  0  0  0
 14 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000872

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CCCCCCCCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H26O4/c15-13(16)11-9-7-5-3-1-2-4-6-8-10-12-14(17)18/h1-12H2,(H,15,16)(H,17,18)

> <INCHI_KEY>
HQHCYKULIHKCEB-UHFFFAOYSA-N

> <FORMULA>
C14H26O4

> <MOLECULAR_WEIGHT>
258.3538

> <EXACT_MASS>
258.18310932

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.10951226001032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
tetradecanedioic acid

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
4.047203682666666

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.253049650892543

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.650989659564581

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
69.547

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetradecanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000872
     RDKit          3D
Tetradecanedioic acid
 44 43  0  0  0  0  0  0  0  0999 V2000
    5.9392   -1.7601    1.5377 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3890   -1.5516    0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7906   -1.6029    0.2157 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4902   -1.2669   -0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0714   -1.1112   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9216    0.0482    0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5131    0.2722    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351    0.5188    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1572    0.7319    0.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8732    0.9853   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2207    1.1901    0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904    1.4477   -0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5867    1.6370   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1178    0.5464    0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4537   -0.7538    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4035   -1.5200   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3200   -1.6618   -1.8628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4109   -2.1522    0.1301 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3931   -0.9205    0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8030   -0.2492   -1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5882   -2.0086   -1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -2.0763    0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720   -0.9924   -1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5509   -0.0571    1.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2953    0.9542    0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743   -0.5998    1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    1.1566    1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4699   -0.4195   -0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893    1.3559   -0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -0.1446    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1368    1.5940    1.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892    0.1777   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5691    1.9337   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530    0.3126    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1192    2.1141    0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0398    2.4296   -1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2191    0.7030   -1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3828    1.9732   -0.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4618    2.5584    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670    0.3563    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0764    0.9265    1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3086   -0.5985   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8528   -1.4045    0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0696   -3.0715   -0.1013 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
 15 16  1  0
 16 17  2  0
 16 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 18 44  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Tetrahydro-11-deoxycorticosterone.mol             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       8.002   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.002  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668   1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.336   1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -8.002   0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -9.336  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2   15   16                                                  
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   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   17   18                                                  
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17   14                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

COMPND    HMDB0000872
HETATM    1  O1  UNL     1       5.939  -1.760   1.538  1.00  0.00           O  
HETATM    2  C1  UNL     1       6.389  -1.552   0.388  1.00  0.00           C  
HETATM    3  O2  UNL     1       7.791  -1.603   0.216  1.00  0.00           O  
HETATM    4  C2  UNL     1       5.490  -1.267  -0.725  1.00  0.00           C  
HETATM    5  C3  UNL     1       4.071  -1.111  -0.275  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.922   0.048   0.630  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.513   0.272   1.120  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.535   0.519   0.011  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.157   0.732   0.600  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.873   0.985  -0.475  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.221   1.190   0.173  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.290   1.448  -0.879  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.587   1.637  -0.193  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.118   0.546   0.644  1.00  0.00           C  
HETATM   15  C13 UNL     1      -5.454  -0.754   0.040  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.403  -1.520  -0.617  1.00  0.00           C  
HETATM   17  O3  UNL     1      -4.320  -1.662  -1.863  1.00  0.00           O  
HETATM   18  O4  UNL     1      -3.411  -2.152   0.130  1.00  0.00           O  
HETATM   19  H1  UNL     1       8.393  -0.920   0.678  1.00  0.00           H  
HETATM   20  H2  UNL     1       5.803  -0.249  -1.122  1.00  0.00           H  
HETATM   21  H3  UNL     1       5.588  -2.009  -1.555  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.759  -2.076   0.199  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.472  -0.992  -1.229  1.00  0.00           H  
HETATM   24  H6  UNL     1       4.551  -0.057   1.518  1.00  0.00           H  
HETATM   25  H7  UNL     1       4.295   0.954   0.096  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.174  -0.600   1.707  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.533   1.157   1.788  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.470  -0.419  -0.597  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.789   1.356  -0.637  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.186  -0.145   1.183  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.137   1.594   1.298  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.889   0.178  -1.230  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.569   1.934  -1.003  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.453   0.313   0.801  1.00  0.00           H  
HETATM   35  H17 UNL     1      -2.119   2.114   0.814  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.040   2.430  -1.374  1.00  0.00           H  
HETATM   37  H19 UNL     1      -3.219   0.703  -1.659  1.00  0.00           H  
HETATM   38  H20 UNL     1      -5.383   1.973  -0.914  1.00  0.00           H  
HETATM   39  H21 UNL     1      -4.462   2.558   0.464  1.00  0.00           H  
HETATM   40  H22 UNL     1      -4.467   0.356   1.548  1.00  0.00           H  
HETATM   41  H23 UNL     1      -6.076   0.926   1.129  1.00  0.00           H  
HETATM   42  H24 UNL     1      -6.309  -0.599  -0.689  1.00  0.00           H  
HETATM   43  H25 UNL     1      -5.853  -1.404   0.877  1.00  0.00           H  
HETATM   44  H26 UNL     1      -3.070  -3.071  -0.101  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   19
CONECT    4    5   20   21
CONECT    5    6   22   23
CONECT    6    7   24   25
CONECT    7    8   26   27
CONECT    8    9   28   29
CONECT    9   10   30   31
CONECT   10   11   32   33
CONECT   11   12   34   35
CONECT   12   13   36   37
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16   42   43
CONECT   16   17   17   18
CONECT   18   44
END

HMDB0000872
     RDKit          3D
Tetradecanedioic acid
 44 43  0  0  0  0  0  0  0  0999 V2000
    5.9392   -1.7601    1.5377 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3890   -1.5516    0.3883 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7906   -1.6029    0.2157 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4902   -1.2669   -0.7250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0714   -1.1112   -0.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9216    0.0482    0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5131    0.2722    1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5351    0.5188    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1572    0.7319    0.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8732    0.9853   -0.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2207    1.1901    0.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2904    1.4477   -0.8793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5867    1.6370   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1178    0.5464    0.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4537   -0.7538    0.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4035   -1.5200   -0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3200   -1.6618   -1.8628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4109   -2.1522    0.1301 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3931   -0.9205    0.6778 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8030   -0.2492   -1.1224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5882   -2.0086   -1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7586   -2.0763    0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4720   -0.9924   -1.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5509   -0.0571    1.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2953    0.9542    0.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1743   -0.5998    1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326    1.1566    1.7881 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4699   -0.4195   -0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893    1.3559   -0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1860   -0.1446    1.1834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1368    1.5940    1.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8892    0.1777   -1.2299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5691    1.9337   -1.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530    0.3126    0.8007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1192    2.1141    0.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0398    2.4296   -1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2191    0.7030   -1.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3828    1.9732   -0.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4618    2.5584    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670    0.3563    1.5484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0764    0.9265    1.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3086   -0.5985   -0.6893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8528   -1.4045    0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0696   -3.0715   -0.1013 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
 15 16  1  0
 16 17  2  0
 16 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  0
 15 43  1  0
 18 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,12-Dodecanedicarboxylic acid	ChEBI
1,14-Tetradecanedioic acid	ChEBI
Dodecamethylenedicarboxylic acid	ChEBI
NSC 9504	ChEBI
Tetradecane-1,14-dioic acid	ChEBI
1,12-Dodecanedicarboxylate	Generator
1,14-Tetradecanedioate	Generator
Dodecamethylenedicarboxylate	Generator
Tetradecane-1,14-dioate	Generator
Tetradecanedioate	Generator
Tetradecanedicarboxylate	HMDB
Tetradecanedicarboxylic acid	HMDB

Chemical Formula

C₁₄H₂₆O₄

Average Molecular Weight

258.3538

Monoisotopic Molecular Weight

258.18310932

IUPAC Name

tetradecanedioic acid

Traditional Name

tetradecanedioic acid

CAS Registry Number

821-38-5

SMILES

OC(=O)CCCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C14H26O4/c15-13(16)11-9-7-5-3-1-2-4-6-8-10-12-14(17)18/h1-12H2,(H,15,16)(H,17,18)

InChI Key

HQHCYKULIHKCEB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,omega-dicarboxylic acid (CHEBI:76308 )
Dicarboxylic acids (LMFA01170018 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2308028)

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0000872)

Excreta

Biofluid or Excreta

Feces (PMID: 27015276)
Urine (HMDB: HMDB0000872)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000872)

Source

Endogenous

Endogenous (HMDB: HMDB0000872)

Animal

Animal (HMDB: HMDB0000872)

Exogenous

Food

Food (HMDB: HMDB0000872)

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)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0000872)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0000872)

Lipid metabolism pathway (HMDB: HMDB0000872)

Biochemical process

Lipid transport (HMDB: HMDB0000872)

Role

Biological role

Energy source (HMDB: HMDB0000872)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.2 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.036 g/L	ALOGPS
logP	3.63	ALOGPS
logP	4.05	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	69.55 m³·mol⁻¹	ChemAxon
Polarizability	31.11 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]+	165.012	31661259
DarkChem	[M-H]-	163.296	31661259
AllCCS	[M+H]+	163.799	32859911
AllCCS	[M-H]-	166.513	32859911
DeepCCS	[M+H]+	161.216	30932474
DeepCCS	[M-H]-	157.331	30932474
DeepCCS	[M-2H]-	195.145	30932474
DeepCCS	[M+Na]+	170.808	30932474
AllCCS	[M+H]+	163.8	32859911
AllCCS	[M+H-H2O]+	160.6	32859911
AllCCS	[M+NH4]+	166.7	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	166.5	32859911
AllCCS	[M+Na-2H]-	167.4	32859911
AllCCS	[M+HCOO]-	168.5	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.	8.88 minutes	32390414
Predicted by Siyang on May 30, 2022	14.733 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.84 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	36.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2427.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	328.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	173.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	185.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	437.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	573.7 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	593.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	117.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1364.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	464.5 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	1379.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	477.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	376.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	503.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	331.1 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	160.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetradecanedioic acid	OC(=O)CCCCCCCCCCCCC(O)=O	3206.5	Standard polar	33892256
Tetradecanedioic acid	OC(=O)CCCCCCCCCCCCC(O)=O	1967.4	Standard non polar	33892256
Tetradecanedioic acid	OC(=O)CCCCCCCCCCCCC(O)=O	2150.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tetradecanedioic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCCCCCCC(=O)O	2218.2	Semi standard non polar	33892256
Tetradecanedioic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCCCCCCC(=O)O[Si](C)(C)C	2308.2	Semi standard non polar	33892256
Tetradecanedioic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCC(=O)O	2476.5	Semi standard non polar	33892256
Tetradecanedioic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2832.8	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces
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
Blood	Detected and Quantified	0.11(0.078-0.19) uM	Infant (0-1 year old)	Not Specified	Normal	2308028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.088-3.4 uM	Infant (0-1 year old)	Female	3-Hydroxydicarboxylic aciduria	2308028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022293

KNApSAcK ID

C00053820

Chemspider ID

12630

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5833

PubChem Compound

13185

PDB ID

Not Available

ChEBI ID

76308

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Chen, Yuandong; Hao, Xiuzhen. Method for producing tetradecanedioic acid by bioconversion of n-tetradecane. Faming Zhuanli Shenqing Gongkai Shuomingshu (2002), 10 pp.

Material Safety Data Sheet (MSDS)

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General References

Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
Ziegler I, Fink M, Wilmanns W: Biopterin level in peripheral blood cells as a marker for hemopoietic cell proliferation during leukemia and polycythemia vera. Blut. 1982 Apr;44(4):231-40. [PubMed:6952953 ]

Showing metabocard for Tetradecanedioic acid (HMDB0000872)

MOL for HMDB0000872 (Tetradecanedioic acid)

3D MOL for HMDB0000872 (Tetradecanedioic acid)

3D SDF for HMDB0000872 (Tetradecanedioic acid)

3D-SDF for HMDB0000872 (Tetradecanedioic acid)

PDB for HMDB0000872 (Tetradecanedioic acid)

3D PDB for HMDB0000872 (Tetradecanedioic acid)

SMILES for HMDB0000872 (Tetradecanedioic acid)

INCHI for HMDB0000872 (Tetradecanedioic acid)

Structure for HMDB0000872 (Tetradecanedioic acid)

3D Structure for HMDB0000872 (Tetradecanedioic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized