Showing metabocard for trans-Aconitic acid (MMDBc0000176)

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:0x00007f922d4183b0>


  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
Download

3D MOL for #<Metabolite:0x00007f922d4183b0>

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:0x00007f922d4183b0>


  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:0x00007f922d4183b0>

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:0x00007f922d4183b0>

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:0x00007f922d4183b0>

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:0x00007f922d4183b0>

OC(=O)C\C(=C/C(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007f922d4183b0>

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
ValueSource
(1E)-1-Propene-1,2,3-tricarboxylic acidChEBI
(e)-1-Propene-1,2,3-tricarboxylic acidChEBI
(1E)-1-Propene-1,2,3-tricarboxylateGenerator
(e)-1-Propene-1,2,3-tricarboxylateGenerator
trans-AconitateGenerator
(1E)-Prop-1-ene-1,2,3-tricarboxylicHMDB
(1E)1-Propene-1,2,3-tricarboxylateHMDB
(1E)1-Propene-1,2,3-tricarboxylic acidHMDB
(e)-Aconitic acidHMDB
1-Propene-1-trans-2,3-tricarboxylic acidHMDB
1-trans-Propene-1,2,3-tricarboxylic acidHMDB
AcidHMDB
TRAHMDB
trans-1-Propene-1,2,3-tricarboxylic acidHMDB
trans-Propene-1,2,3-tricarboxylic acidHMDB
Acid, aconiticHMDB
Acid, adonicHMDB
Acid, carboxyglutaconicHMDB
Acid, citridicHMDB
Adonic acidHMDB
Achilleic acidHMDB
Acid, aconticHMDB
Acid, pyrocitricHMDB
Carboxyglutaconic acidHMDB
Equisetic acidHMDB
Pyrocitric acidHMDB
Acid, achilleicHMDB
Acid, equiseticHMDB
AconitateHMDB
Citridic acidHMDB
Citridinic acidHMDB
Acid, citridinicHMDB
Aconitic acidHMDB
Acontic acidHMDB
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