Showing metabocard for 1,2,3-Propanetricarboxylic acid (MMDBc0000478)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:38:40 UTC
Update Date2024-04-30 19:32:34 UTC
Metabolite IDMMDBc0000478
Metabolite Identification
Common Name1,2,3-Propanetricarboxylic acid
Description1,2,3-Propanetricarboxylic acid is found in corn. 1,2,3-Propanetricarboxylic acid is isolated from plants e.g. sugarbeet sap, sap of Acer saccharinum (maple syrup). Propane-1,2,3-tricarboxylic acid, also known as tricarballylic acid, carballylic acid, and beta-carboxyglutaric acid, is a tricarboxylic acid that has three carboxylic acid functional groups. The compound is an inhibitor of the enzyme aconitase and interferes with the Krebs cycle. 1,2,3-Propanetricarboxylic acid can be produced by Bacteroides, Butyrivibrio, Megasphaera, Wolinella and fungi Nectriaceae (PMID:22815244 ; PMID:16346691 ). It is also associated with Fumonisins. Fumonisins are fungal toxins produced by Fusarium verticilloides. Detection of this compound indicates presence of fumonisins in gastrointestinal tract. Corn intake or corn contaminated with fumonisins can lead to increased levels of tricarballylic acid (PMID:22815244 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fd12d49b870>


  Mrv1652305261923522D          

 12 11  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fd12d49b870>

HMDB0031193
     RDKit          3D
1,2,3-Propanetricarboxylic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -1.9615   -1.4811   -1.5952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2746   -0.7918   -0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2712   -1.2616    0.2255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5962    0.4702   -0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2374    0.3009    0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -0.5097   -0.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9998   -0.7493    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3204   -0.4165    1.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9808   -1.4023   -0.6231 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440    1.6951    0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236    2.7098    0.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233    1.9249    1.2536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139   -1.8589    1.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3698    1.0559   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833    1.1702    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -0.1526    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2421   -1.4684   -0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872    0.1002   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769   -1.6603   -0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034    2.3253    0.7515 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  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
  4 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  9 19  1  0
 12 20  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fd12d49b870>


  Mrv1652305261923522D          

 12 11  0  0  0  0            999 V2000
    1.7605    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000478

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CC(CC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O6/c7-4(8)1-3(6(11)12)2-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

> <INCHI_KEY>
KQTIIICEAUMSDG-UHFFFAOYSA-N

> <FORMULA>
C6H8O6

> <MOLECULAR_WEIGHT>
176.1241

> <EXACT_MASS>
176.032087988

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.79262659473791

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
propane-1,2,3-tricarboxylic acid

> <ALOGPS_LOGP>
-0.56

> <JCHEM_LOGP>
-0.7311697890000002

> <ALOGPS_LOGS>
-0.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.856543738559703

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.594567578813867

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
34.377900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tricarballylic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fd12d49b870>

HMDB0031193
     RDKit          3D
1,2,3-Propanetricarboxylic acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -1.9615   -1.4811   -1.5952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2746   -0.7918   -0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2712   -1.2616    0.2255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5962    0.4702   -0.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2374    0.3009    0.3487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -0.5097   -0.4859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9998   -0.7493    0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3204   -0.4165    1.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9808   -1.4023   -0.6231 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2440    1.6951    0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4236    2.7098    0.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233    1.9249    1.2536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1139   -1.8589    1.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3698    1.0559   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833    1.1702    0.2970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -0.1526    1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2421   -1.4684   -0.8300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872    0.1002   -1.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8769   -1.6603   -0.2792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2034    2.3253    0.7515 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  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
  4 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  9 19  1  0
 12 20  1  0
M  END
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PDB for #<Metabolite:0x00007fd12d49b870>

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0       3.286   3.437   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.620   1.127   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.287   1.127   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.621   0.357   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.954   0.357   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for #<Metabolite:0x00007fd12d49b870>

COMPND    HMDB0031193
HETATM    1  O1  UNL     1      -1.962  -1.481  -1.595  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.275  -0.792  -0.602  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.271  -1.262   0.225  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.596   0.470  -0.338  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.237   0.301   0.349  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.687  -0.510  -0.486  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.000  -0.749   0.134  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.320  -0.416   1.293  1.00  0.00           O  
HETATM    9  O4  UNL     1       2.981  -1.402  -0.623  1.00  0.00           O  
HETATM   10  C6  UNL     1       0.244   1.695   0.592  1.00  0.00           C  
HETATM   11  O5  UNL     1      -0.424   2.710   0.195  1.00  0.00           O  
HETATM   12  O6  UNL     1       1.423   1.925   1.254  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.114  -1.859   1.027  1.00  0.00           H  
HETATM   14  H2  UNL     1      -1.370   1.056  -1.273  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.183   1.170   0.297  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.433  -0.153   1.329  1.00  0.00           H  
HETATM   17  H5  UNL     1       0.242  -1.468  -0.830  1.00  0.00           H  
HETATM   18  H6  UNL     1       0.887   0.100  -1.420  1.00  0.00           H  
HETATM   19  H7  UNL     1       3.877  -1.660  -0.279  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.203   2.325   0.751  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5   14   15
CONECT    5    6   10   16
CONECT    6    7   17   18
CONECT    7    8    8    9
CONECT    9   19
CONECT   10   11   11   12
CONECT   12   20
END
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SMILES for #<Metabolite:0x00007fd12d49b870>

OC(=O)CC(CC(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007fd12d49b870>

InChI=1S/C6H8O6/c7-4(8)1-3(6(11)12)2-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
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Synonyms
ValueSource
3-Carboxyglutaric acidChEBI
3-Carboxypentanedioic acidChEBI
beta-Carboxyglutaric acidChEBI
Carballylic acidChEBI
Carboxymethylsuccinic acidChEBI
TricarballylateKegg
3-CarboxyglutarateGenerator
3-CarboxypentanedioateGenerator
b-CarboxyglutarateGenerator
b-Carboxyglutaric acidGenerator
beta-CarboxyglutarateGenerator
Β-carboxyglutarateGenerator
Β-carboxyglutaric acidGenerator
CarballylateGenerator
CarboxymethylsuccinateGenerator
Tricarballylic acidGenerator
1,2,3-PropanetricarboxylateGenerator
1,2,3-Tripropanetricarboxylic acidHMDB
Propane 1,2,3-tricarboxylic acidHMDB
Tricarballylic acid, trisodium saltMeSH, HMDB
Propane-1,2,3-tricarboxylateMeSH, HMDB
Tricarballylic acid, sodium saltMeSH, HMDB
1,2,3-Propanetricarboxylic acidChEBI
Molecular FormulaC6H8O6
Average Mass176.1241
Monoisotopic Mass176.032087988
IUPAC Namepropane-1,2,3-tricarboxylic acid
Traditional Nametricarballylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H8O6/c7-4(8)1-3(6(11)12)2-5(9)10/h3H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChI KeyKQTIIICEAUMSDG-UHFFFAOYSA-N