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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:07 UTC

HMDB ID

HMDB0000933

Secondary Accession Numbers

HMDB00933

Metabolite Identification

Common Name

Traumatic acid

Description

Traumatic acid is a monounsaturated dicarboxylic acid naturally ocurring in plants. The compound was first isolated from wounded bean plants by American chemists James English Jr. and James Frederick Bonner and Dutch scientist Aire Jan Haagen-Smit in 1939. Traumatic acid is a potent wound healing agent in plants ("wound hormone") that stimulates cell division near a trauma site to form a protective callus and to heal the damaged tissue. It may also act as a growth hormone, especially in inferior plants (e.g. algae). Traumatic acid is biosynthesized in plants by non-enzimatic oxidation of traumatin (12-oxo-trans-10-dodecanoic acid), another wound hormone. At normal conditions, traumatic acid is a solid, crystalized, water insoluble substance.

Structure

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

HMDB0000933
     RDKit          3D
Traumatic acid
 36 35  0  0  0  0  0  0  0  0999 V2000
   -6.7305    0.2045   -2.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2542   -0.0001   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1196   -0.4033    0.1104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8158    0.1933   -0.6682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2644   -0.0077    0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7871    0.1898    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0860    0.6214   -0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6189    0.8126   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0679   -0.4078    0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242   -0.1586    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3209    0.2905   -0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7786    0.5409   -0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4369   -0.7057    0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8942   -0.4580    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3418    0.6875    0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6328   -1.5315    0.9801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0877    0.1069    0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1804    0.5059   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8993   -0.3236    1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832    0.8940    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -0.8137    1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350   -0.0643   -1.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4740    1.6328   -0.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129    1.2636   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    1.5654    0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0467   -1.1631   -0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4093   -0.8666    1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5421    0.5806    1.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9842   -1.1047    1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567    1.2242   -0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2541   -0.4885   -1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2798    0.8361   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8524    1.3808    0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9642   -1.0925    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -1.4533   -0.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4799   -2.4881    0.6448 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  2  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  2  0
 14 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
M  END


  Mrv1652305271900312D          

 16 15  0  0  0  0            999 V2000
   23.7979   -7.5166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0834   -8.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5104   -7.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2248   -6.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5113   -7.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2258   -7.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7969   -7.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9402   -7.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0826   -7.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6546   -7.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3680   -7.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3691   -7.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6537   -7.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0834   -7.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9392   -7.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2248   -7.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2 14  2  0  0  0  0
  3 16  1  0  0  0  0
  4 16  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000933

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h7,9H,1-6,8,10H2,(H,13,14)(H,15,16)/b9-7+

> <INCHI_KEY>
MAZWDMBCPDUFDJ-VQHVLOKHSA-N

> <FORMULA>
C12H20O4

> <MOLECULAR_WEIGHT>
228.2848

> <EXACT_MASS>
228.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
26.06205161412626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-dodec-2-enedioic acid

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
3.1558898423333335

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.324346188153568

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.722275115342478

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
61.438300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
traumatic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000933
     RDKit          3D
Traumatic acid
 36 35  0  0  0  0  0  0  0  0999 V2000
   -6.7305    0.2045   -2.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2542   -0.0001   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1196   -0.4033    0.1104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8158    0.1933   -0.6682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2644   -0.0077    0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7871    0.1898    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0860    0.6214   -0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6189    0.8126   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0679   -0.4078    0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242   -0.1586    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3209    0.2905   -0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7786    0.5409   -0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4369   -0.7057    0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8942   -0.4580    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3418    0.6875    0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6328   -1.5315    0.9801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0877    0.1069    0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1804    0.5059   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8993   -0.3236    1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832    0.8940    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -0.8137    1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350   -0.0643   -1.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4740    1.6328   -0.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129    1.2636   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    1.5654    0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0467   -1.1631   -0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4093   -0.8666    1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5421    0.5806    1.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9842   -1.1047    1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567    1.2242   -0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2541   -0.4885   -1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2798    0.8361   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8524    1.3808    0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9642   -1.0925    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -1.4533   -0.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4799   -2.4881    0.6448 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  2  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  2  0
 14 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      44.423 -14.031   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      43.089 -16.341   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      27.086 -14.801   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      28.420 -12.491   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      36.421 -14.031   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      37.755 -14.801   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.088 -14.801   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.088 -14.031   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.754 -14.031   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      40.422 -14.801   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.420 -14.801   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      41.756 -14.031   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.087 -14.031   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      43.089 -14.801   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.753 -14.801   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.420 -14.031   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   16                                                            
CONECT    4   16                                                            
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14    1    2   12                                                  
CONECT   15   13   16                                                       
CONECT   16    3    4   15                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0000933
HETATM    1  O1  UNL     1      -6.730   0.205  -2.033  1.00  0.00           O  
HETATM    2  C1  UNL     1      -6.254  -0.000  -0.893  1.00  0.00           C  
HETATM    3  O2  UNL     1      -7.120  -0.403   0.110  1.00  0.00           O  
HETATM    4  C2  UNL     1      -4.816   0.193  -0.668  1.00  0.00           C  
HETATM    5  C3  UNL     1      -4.264  -0.008   0.510  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.787   0.190   0.745  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.086   0.621  -0.495  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.619   0.813  -0.176  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.068  -0.408   0.315  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.524  -0.159   0.622  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.321   0.290  -0.546  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.779   0.541  -0.252  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.437  -0.706   0.238  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.894  -0.458   0.517  1.00  0.00           C  
HETATM   15  O3  UNL     1       6.342   0.687   0.316  1.00  0.00           O  
HETATM   16  O4  UNL     1       6.633  -1.532   0.980  1.00  0.00           O  
HETATM   17  H1  UNL     1      -7.088   0.107   0.988  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.180   0.506  -1.467  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.899  -0.324   1.326  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.583   0.894   1.553  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.405  -0.814   1.085  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.235  -0.064  -1.354  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.474   1.633  -0.777  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.113   1.264  -1.048  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.596   1.565   0.666  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.047  -1.163  -0.501  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.409  -0.867   1.204  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.542   0.581   1.471  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.984  -1.105   1.031  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.857   1.224  -0.986  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.254  -0.488  -1.358  1.00  0.00           H  
HETATM   32  H16 UNL     1       4.280   0.836  -1.198  1.00  0.00           H  
HETATM   33  H17 UNL     1       3.852   1.381   0.475  1.00  0.00           H  
HETATM   34  H18 UNL     1       3.964  -1.093   1.178  1.00  0.00           H  
HETATM   35  H19 UNL     1       4.401  -1.453  -0.582  1.00  0.00           H  
HETATM   36  H20 UNL     1       6.480  -2.488   0.645  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   17
CONECT    4    5    5   18
CONECT    5    6   19
CONECT    6    7   20   21
CONECT    7    8   22   23
CONECT    8    9   24   25
CONECT    9   10   26   27
CONECT   10   11   28   29
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14   34   35
CONECT   14   15   15   16
CONECT   16   36
END

HMDB0000933
     RDKit          3D
Traumatic acid
 36 35  0  0  0  0  0  0  0  0999 V2000
   -6.7305    0.2045   -2.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2542   -0.0001   -0.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1196   -0.4033    0.1104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8158    0.1933   -0.6682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2644   -0.0077    0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7871    0.1898    0.7445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0860    0.6214   -0.4953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6189    0.8126   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0679   -0.4078    0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242   -0.1586    0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3209    0.2905   -0.5463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7786    0.5409   -0.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4369   -0.7057    0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8942   -0.4580    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3418    0.6875    0.3159 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6328   -1.5315    0.9801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0877    0.1069    0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1804    0.5059   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8993   -0.3236    1.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832    0.8940    1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -0.8137    1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2350   -0.0643   -1.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4740    1.6328   -0.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129    1.2636   -1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    1.5654    0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0467   -1.1631   -0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4093   -0.8666    1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5421    0.5806    1.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9842   -1.1047    1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8567    1.2242   -0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2541   -0.4885   -1.3583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2798    0.8361   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8524    1.3808    0.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9642   -1.0925    1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -1.4533   -0.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4799   -2.4881    0.6448 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  2  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  2  0
 14 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E)-Dodecenedioic acid	ChEBI
2E-Dodecenedioic acid	ChEBI
Dodec-2-enedioic acid	ChEBI
trans-2-Dodecenedioic acid	ChEBI
(2E)-Dodecenedioate	Generator
2E-Dodecenedioate	Generator
Dodec-2-enedioate	Generator
trans-2-Dodecenedioate	Generator
Traumatate	Generator
(Z)-2-Dodecenedioate	HMDB
(Z)-2-Dodecenedioic acid	HMDB
1-Decene-1,10-dicarboxylic acid	HMDB
2-Dodecendioate	HMDB
2-Dodecendioic acid	HMDB
2-Dodecenedioate	HMDB
2-Dodecenedioic acid	HMDB
Dodec-2C-enedioate	HMDB
Dodec-2C-enedioic acid	HMDB
Dodec-2t-enedioate	HMDB
Dodec-2t-enedioic acid	HMDB
Dodecanedioate	HMDB
Dodecanedioic acid	HMDB
Dodecanedioic acid-2-ene	HMDB
trans-Traumatate	HMDB
trans-Traumatic acid	HMDB
2-Dodecene-1,12-dicarboxylic acid	HMDB

Chemical Formula

C₁₂H₂₀O₄

Average Molecular Weight

228.2848

Monoisotopic Molecular Weight

228.136159128

IUPAC Name

(2E)-dodec-2-enedioic acid

Traditional Name

traumatic acid

CAS Registry Number

6402-36-4

SMILES

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

InChI Identifier

InChI=1S/C12H20O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h7,9H,1-6,8,10H2,(H,13,14)(H,15,16)/b9-7+

InChI Key

MAZWDMBCPDUFDJ-VQHVLOKHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Unsaturated 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

dicarboxylic acid (CHEBI:545687 )
Dicarboxylic acids (LMFA01170002 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165.5 °C	Not Available
Boiling Point	376.00 to 377.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	229.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.686 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	149.852	30932474
[M-H]-	Not Available	149.852	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000228

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	2.96	ALOGPS
logP	3.16	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.72	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	10	ChemAxon
Refractivity	61.44 m³·mol⁻¹	ChemAxon
Polarizability	26.06 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]+	157.212	31661259
DarkChem	[M-H]-	155.047	31661259
AllCCS	[M+H]+	153.586	32859911
AllCCS	[M-H]-	156.799	32859911
DeepCCS	[M+H]+	153.746	30932474
DeepCCS	[M-H]-	149.727	30932474
DeepCCS	[M-2H]-	187.56	30932474
DeepCCS	[M+Na]+	163.224	30932474
AllCCS	[M+H]+	153.6	32859911
AllCCS	[M+H-H2O]+	150.1	32859911
AllCCS	[M+NH4]+	156.8	32859911
AllCCS	[M+Na]+	157.7	32859911
AllCCS	[M-H]-	156.8	32859911
AllCCS	[M+Na-2H]-	157.8	32859911
AllCCS	[M+HCOO]-	158.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.39 minutes	32390414
Predicted by Siyang on May 30, 2022	13.772 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.59 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2214.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	333.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	198.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	530.8 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	536.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	116.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1262.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	443.3 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	1320.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	425.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	371.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	452.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	340.7 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	93.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Traumatic acid	OC(=O)CCCCCCCC\C=C\C(O)=O	3295.1	Standard polar	33892256
Traumatic acid	OC(=O)CCCCCCCC\C=C\C(O)=O	1742.2	Standard non polar	33892256
Traumatic acid	OC(=O)CCCCCCCC\C=C\C(O)=O	1955.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Traumatic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CCCCCCCC/C=C/C(=O)O	2080.4	Semi standard non polar	33892256
Traumatic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)/C=C/CCCCCCCCC(=O)O	2066.5	Semi standard non polar	33892256
Traumatic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C/CCCCCCCCC(=O)O[Si](C)(C)C	2130.2	Semi standard non polar	33892256
Traumatic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC/C=C/C(=O)O	2313.6	Semi standard non polar	33892256
Traumatic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C=C/CCCCCCCCC(=O)O	2294.5	Semi standard non polar	33892256
Traumatic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C/CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2604.3	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
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
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

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	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 Available	Not Available	Ketosis	11978597	details
Urine	Detected but not Quantified	Not Quantified	Not Available	Not Available	Very long-chain acyl-CoA dehydrogenase deficiency (vLCAD)	11978597	details
Urine	Detected but not Quantified	Not Quantified	Not Available	Not Available	LCHAD/Trifunctional Protein Deficiency	11978597	details
Urine	Detected but not Quantified	Not Quantified	Not Available	Not Available	Myoadenylate deaminase deficiency	11978597	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 ]
Ketosis
Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
Very Long Chain Acyl-CoA Dehydrogenase Deficiency
Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
Mitochondrial trifunctional protein deficiency
Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]
Myoadenylate deaminase deficiency
Kumps A, Duez P, Mardens Y: Metabolic, nutritional, iatrogenic, and artifactual sources of urinary organic acids: a comprehensive table. Clin Chem. 2002 May;48(5):708-17. [PubMed:11978597 ]

Associated OMIM IDs

114500 (Colorectal cancer)
201475 (Very Long Chain Acyl-CoA Dehydrogenase Deficiency)
609015 (Mitochondrial trifunctional protein deficiency)
102770 (Myoadenylate deaminase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006541

KNApSAcK ID

Not Available

Chemspider ID

4446155

KEGG Compound ID

C16308

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Traumatic acid

METLIN ID

5882

PubChem Compound

5283028

PDB ID

Not Available

ChEBI ID

545687

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1291501

References

Synthesis Reference

Dupont, G.; Dulou, R.; Quantin, P. Polycarboxylic acids and their derivatives. (1952), FR 1018186 19521229 CAN 52:6571 AN 1958:6571

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Showing metabocard for Traumatic acid (HMDB0000933)

MOL for HMDB0000933 (Traumatic acid)

3D MOL for HMDB0000933 (Traumatic acid)

3D SDF for HMDB0000933 (Traumatic acid)

3D-SDF for HMDB0000933 (Traumatic acid)

PDB for HMDB0000933 (Traumatic acid)

3D PDB for HMDB0000933 (Traumatic acid)

SMILES for HMDB0000933 (Traumatic acid)

INCHI for HMDB0000933 (Traumatic acid)

Structure for HMDB0000933 (Traumatic acid)

3D Structure for HMDB0000933 (Traumatic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized