Showing metabocard for trans-Aconitic acid (MMDBc0000176)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:38:39 UTC
Update Date2024-04-30 19:31:20 UTC
Metabolite IDMMDBc0000176
Metabolite Identification
Common Nametrans-Aconitic acid
Descriptiontrans-Aconitic acid is normally present in normal human urine, and it has been suggested that is present in larger amounts with Reye's syndrome and organic aciduria. trans-Aconitic acid is a substrate of enzyme trans-aconitate 2-methyltransferase (EC 2.1.1.144) (PMID: 7096501 , 4019674 , 2950263 ). Trans-aconitate in the urine is a biomarker for the consumption of soy products.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fd5d48322f8>

  Mrv1652305271900312D          

 12 11  0  0  0  0            999 V2000
   13.3834   -6.2653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6689   -4.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6689   -5.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3834   -2.9652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2414   -3.7902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5268   -5.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0979   -5.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0979   -4.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8124   -3.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3834   -5.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3834   -3.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5268   -4.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3 10  2  0  0  0  0
  4 11  2  0  0  0  0
  5 12  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fd5d48322f8>

HMDB0000958
     RDKit          3D
trans-Aconitic acid
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.3343   -3.1983   -0.6911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1898   -1.9337   -0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3682   -1.2433   -0.4835 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1574   -1.4481   -0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215   -0.2070   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399    0.8774   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3475    1.5626    1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711    1.1945    2.1139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1935    2.6279    1.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9611    0.1289   -0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    1.2971    0.1172 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300   -0.8666   -0.1323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1066   -1.4283   -1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0082   -2.1657   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0402    1.6815   -0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4530    0.7158   -0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683    3.0582    0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8668   -0.6528   -0.4433 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  2  0
  7  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  6 16  1  0
  9 17  1  0
 12 18  1  0
M  END
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3D SDF for #<Metabolite:0x00007fd5d48322f8>

  Mrv1652305271900312D          

 12 11  0  0  0  0            999 V2000
   13.3834   -6.2653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6689   -4.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6689   -5.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3834   -2.9652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2414   -3.7902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5268   -5.0277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0979   -5.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0979   -4.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8124   -3.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3834   -5.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3834   -3.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5268   -4.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3 10  2  0  0  0  0
  4 11  2  0  0  0  0
  5 12  1  0  0  0  0
  6 12  2  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000176

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+

> <INCHI_KEY>
GTZCVFVGUGFEME-HNQUOIGGSA-N

> <FORMULA>
C6H6O6

> <MOLECULAR_WEIGHT>
174.1082

> <EXACT_MASS>
174.016437924

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.9564343716318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1E)-prop-1-ene-1,2,3-tricarboxylic acid

> <ALOGPS_LOGP>
-0.41

> <JCHEM_LOGP>
-0.521036942

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.787966109115829

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.145216334617251

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
35.2305

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trans aconitic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fd5d48322f8>

HMDB0000958
     RDKit          3D
trans-Aconitic acid
 18 17  0  0  0  0  0  0  0  0999 V2000
   -1.3343   -3.1983   -0.6911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1898   -1.9337   -0.5117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3682   -1.2433   -0.4835 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1574   -1.4481   -0.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215   -0.2070   -0.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4399    0.8774   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3475    1.5626    1.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4711    1.1945    2.1139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1935    2.6279    1.5055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9611    0.1289   -0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    1.2971    0.1172 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300   -0.8666   -0.1323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1066   -1.4283   -1.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0082   -2.1657   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0402    1.6815   -0.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4530    0.7158   -0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683    3.0582    0.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8668   -0.6528   -0.4433 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  2  0
  7  9  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  6 16  1  0
  9 17  1  0
 12 18  1  0
M  END
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PDB for #<Metabolite:0x00007fd5d48322f8>

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      24.982 -11.695   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      23.649  -7.845   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      23.649  -9.385   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      24.982  -5.535   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.317  -7.075   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      28.983  -9.385   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      26.316  -9.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.316  -7.845   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.650  -7.075   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.982 -10.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.982  -7.075   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.983  -7.845   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6   12                                                            
CONECT    7    8   10                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   12                                                       
CONECT   10    1    3    7                                                  
CONECT   11    2    4    8                                                  
CONECT   12    5    6    9                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for #<Metabolite:0x00007fd5d48322f8>

COMPND    HMDB0000958
HETATM    1  O1  UNL     1      -1.334  -3.198  -0.691  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.190  -1.934  -0.512  1.00  0.00           C  
HETATM    3  O2  UNL     1      -2.368  -1.243  -0.484  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.157  -1.448  -0.370  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.522  -0.207  -0.186  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.440   0.877  -0.100  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.347   1.563   1.240  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.471   1.194   2.114  1.00  0.00           O  
HETATM    9  O4  UNL     1      -1.193   2.628   1.505  1.00  0.00           O  
HETATM   10  C6  UNL     1       1.961   0.129  -0.058  1.00  0.00           C  
HETATM   11  O5  UNL     1       2.325   1.297   0.117  1.00  0.00           O  
HETATM   12  O6  UNL     1       2.930  -0.867  -0.132  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.107  -1.428  -1.131  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.008  -2.166  -0.416  1.00  0.00           H  
HETATM   15  H3  UNL     1      -0.040   1.682  -0.818  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.453   0.716  -0.429  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.768   3.058   0.793  1.00  0.00           H  
HETATM   18  H6  UNL     1       3.867  -0.653  -0.443  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    5   14
CONECT    5    6   10
CONECT    6    7   15   16
CONECT    7    8    8    9
CONECT    9   17
CONECT   10   11   11   12
CONECT   12   18
END
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SMILES for #<Metabolite:0x00007fd5d48322f8>

OC(=O)C\C(=C/C(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007fd5d48322f8>

InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+
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Synonyms
Molecular FormulaC6H6O6
Average Mass174.1082
Monoisotopic Mass174.016437924
IUPAC Name(1E)-prop-1-ene-1,2,3-tricarboxylic acid
Traditional Nametrans aconitic acid
CAS Registry Number4023-65-8
SMILES
OC(=O)C\C(=C/C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H6O6/c7-4(8)1-3(6(11)12)2-5(9)10/h1H,2H2,(H,7,8)(H,9,10)(H,11,12)/b3-1+
InChI KeyGTZCVFVGUGFEME-HNQUOIGGSA-N