NP-MRD: Showing NP-Card for Traumatic acid (NP0000710)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-19 23:58:22 UTC

NP-MRD ID

NP0000710

Secondary Accession Numbers

None

Natural Product 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>
NP0000710

> <DATABASE_NAME>
NP-MRD

> <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

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
Traumatinate	Generator

Chemical Formula

C₁₂H₂₀O₄

Average Mass

228.2848 Da

Monoisotopic Mass

228.13616 Da

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

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, CD₃OD, 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
Meehania urticifolia	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0000933

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022323

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

Good Scents ID

rw1291501

References

General References

Van Overbeek J: Traumatic Acid and Thiamin as Growth Factors for Algae. Proc Natl Acad Sci U S A. 1940 Jul 15;26(7):441-3. doi: 10.1073/pnas.26.7.441. [PubMed:16588378 ]
Mayer JA, Wone BWM, Alexander DC, Guo L, Ryals JA, Cushman JC: Metabolic profiling of epidermal and mesophyll tissues under water-deficit stress in Opuntia ficus-indica reveals stress-adaptive metabolic responses. Funct Plant Biol. 2021 Jun;48(7):717-731. doi: 10.1071/FP20332. [PubMed:33896444 ]
Jablonska-Trypuc A, Wydro U, Wolejko E, Rodziewicz J, Butarewicz A: Possible Protective Effects of TA on the Cancerous Effect of Mesotrione. Nutrients. 2020 May 8;12(5). pii: nu12051343. doi: 10.3390/nu12051343. [PubMed:32397133 ]
Guan S, Jia B, Chao K, Zhu X, Tang J, Li M, Wu L, Xing L, Liu K, Zhang L, Wang X, Gao X, Huang M: UPLC-QTOF-MS-Based Plasma Lipidomic Profiling Reveals Biomarkers for Inflammatory Bowel Disease Diagnosis. J Proteome Res. 2020 Feb 7;19(2):600-609. doi: 10.1021/acs.jproteome.9b00440. Epub 2019 Dec 26. [PubMed:31821004 ]
Jablonska-Trypuc A, Kretowski R, Wolejko E, Wydro U, Butarewicz A: Traumatic acid toxicity mechanisms in human breast cancer MCF-7cells. Regul Toxicol Pharmacol. 2019 Aug;106:137-146. doi: 10.1016/j.yrtph.2019.04.023. Epub 2019 May 2. [PubMed:31055047 ]
Jablonska-Trypuc A, Wydro U, Wolejko E, Butarewicz A: Toxicological Effects of Traumatic Acid and Selected Herbicides on Human Breast Cancer Cells: In Vitro Cytotoxicity Assessment of Analyzed Compounds. Molecules. 2019 May 2;24(9). pii: molecules24091710. doi: 10.3390/molecules24091710. [PubMed:31052542 ]
Siracusa R, Impellizzeri D, Cordaro M, Gugliandolo E, Peritore AF, Di Paola R, Cuzzocrea S: Topical Application of Adelmidrol + Trans-Traumatic Acid Enhances Skin Wound Healing in a Streptozotocin-Induced Diabetic Mouse Model. Front Pharmacol. 2018 Aug 23;9:871. doi: 10.3389/fphar.2018.00871. eCollection 2018. [PubMed:30190675 ]

Showing NP-Card for Traumatic acid (NP0000710)

MOL for NP0000710 (Traumatic acid)

3D MOL for NP0000710 (Traumatic acid)

3D SDF for NP0000710 (Traumatic acid)

3D-SDF for NP0000710 (Traumatic acid)

PDB for NP0000710 (Traumatic acid)

3D PDB for NP0000710 (Traumatic acid)

SMILES for NP0000710 (Traumatic acid)

INCHI for NP0000710 (Traumatic acid)

Structure for NP0000710 (Traumatic acid)

3D Structure for NP0000710 (Traumatic acid)