Showing metabocard for but-1-ene-1,2,4-tricarboxylic acid (MMDBc0032955)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:28:45 UTC
Update Date2022-08-31 21:49:09 UTC
Metabolite IDMMDBc0032955
Metabolite Identification
Common Namebut-1-ene-1,2,4-tricarboxylic acid
Description(Z)-But-1-ene-1,2,4-tricarboxylate, also known as (Z)-1,2,4-but-1-enetricarboxylic acid or cis-homoaconitate, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups (Z)-But-1-ene-1,2,4-tricarboxylate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (Z)-But-1-ene-1,2,4-tricarboxylate exists in all living species, ranging from bacteria to humans. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f1218ab00c8>


  Mrv1652304032019082D          

 14 13  0  0  0  0            999 V2000
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
 14  3  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f1218ab00c8>

HMDB0060320
     RDKit          3D
(Z)-But-1-ene-1,2,4-tricarboxylate
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.4987   -0.9155   -0.4398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    0.0875   -0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373    1.1939   -1.1788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4141    0.1894   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5818   -0.6982   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8895   -0.3873    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1879    1.0392   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336    1.2741   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3498    1.4427   -1.1290 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924    1.3002    1.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0115   -2.0190    0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1430   -2.5115    0.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0271   -2.9318    0.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6479    2.0375   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9505    1.1692   -0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4183   -1.0531   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1316   -0.5456    1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623    1.7716    0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9472    1.1481   -1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1941    1.4201    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287   -3.0116    1.8675 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  2  0
  8 10  1  0
  5 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 13 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f1218ab00c8>


  Mrv1652304032019082D          

 14 13  0  0  0  0            999 V2000
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  4  3  2  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
 14  3  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032955

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(C(O)=O)=C(/CCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O6/c8-5(9)2-1-4(7(12)13)3-6(10)11/h3H,1-2H2,(H,8,9)(H,10,11)(H,12,13)/b4-3-

> <INCHI_KEY>
BJYPZFUWWJSAKC-ARJAWSKDSA-N

> <FORMULA>
C7H8O6

> <MOLECULAR_WEIGHT>
188.1348

> <EXACT_MASS>
188.032087988

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.16506685088934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1Z)-but-1-ene-1,2,4-tricarboxylic acid

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-0.07646827699999999

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.9026760660494837

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.282652717735654

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999999

> <JCHEM_REFRACTIVITY>
39.831500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
homo-cis-aconitate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007f1218ab00c8>

HMDB0060320
     RDKit          3D
(Z)-But-1-ene-1,2,4-tricarboxylate
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.4987   -0.9155   -0.4398 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8233    0.0875   -0.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373    1.1939   -1.1788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4141    0.1894   -0.4617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5818   -0.6982   -0.0156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8895   -0.3873    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1879    1.0392   -0.2710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336    1.2741   -0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3498    1.4427   -1.1290 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1924    1.3002    1.1446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0115   -2.0190    0.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1430   -2.5115    0.3252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0271   -2.9318    0.8555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6479    2.0375   -0.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9505    1.1692   -0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4183   -1.0531   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1316   -0.5456    1.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6623    1.7716    0.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9472    1.1481   -1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1941    1.4201    1.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0287   -3.0116    1.8675 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  2  0
  8 10  1  0
  5 11  1  0
 11 12  2  0
 11 13  1  0
  3 14  1  0
  4 15  1  0
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 13 21  1  0
M  END
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PDB for #<Metabolite:0x00007f1218ab00c8>

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.620  -2.667   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.310  -4.001   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.310   1.334   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    4    6   14                                                  
CONECT    4    1    3    7                                                  
CONECT    5    2    8    9                                                  
CONECT    6    3   10   11                                                  
CONECT    7    4   12   13                                                  
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    7                                                            
CONECT   14    3                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END
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3D PDB for #<Metabolite:0x00007f1218ab00c8>

COMPND    HMDB0060320
HETATM    1  O1  UNL     1      -3.499  -0.915  -0.440  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.823   0.088  -0.672  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.537   1.194  -1.179  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.414   0.189  -0.462  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.582  -0.698  -0.016  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.889  -0.387   0.134  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.188   1.039  -0.271  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.634   1.274  -0.117  1.00  0.00           C  
HETATM    9  O3  UNL     1       3.350   1.443  -1.129  1.00  0.00           O  
HETATM   10  O4  UNL     1       3.192   1.300   1.145  1.00  0.00           O  
HETATM   11  C7  UNL     1      -1.012  -2.019   0.361  1.00  0.00           C  
HETATM   12  O5  UNL     1      -2.143  -2.511   0.325  1.00  0.00           O  
HETATM   13  O6  UNL     1      -0.027  -2.932   0.855  1.00  0.00           O  
HETATM   14  H1  UNL     1      -3.648   2.038  -0.632  1.00  0.00           H  
HETATM   15  H2  UNL     1      -0.950   1.169  -0.712  1.00  0.00           H  
HETATM   16  H3  UNL     1       1.418  -1.053  -0.575  1.00  0.00           H  
HETATM   17  H4  UNL     1       1.132  -0.546   1.195  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.662   1.772   0.373  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.947   1.148  -1.347  1.00  0.00           H  
HETATM   20  H7  UNL     1       4.194   1.420   1.295  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.029  -3.012   1.868  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    5   15
CONECT    5    6   11
CONECT    6    7   16   17
CONECT    7    8   18   19
CONECT    8    9    9   10
CONECT   10   20
CONECT   11   12   12   13
CONECT   13   21
END
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SMILES for #<Metabolite:0x00007f1218ab00c8>

[H]\C(C(O)=O)=C(/CCC(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007f1218ab00c8>

InChI=1S/C7H8O6/c8-5(9)2-1-4(7(12)13)3-6(10)11/h3H,1-2H2,(H,8,9)(H,10,11)(H,12,13)/b4-3-
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Synonyms
ValueSource
(Z)-1,2,4-But-1-enetricarboxylic acidChEBI
But-1-ene-1,2,4-tricarboxylateChEBI
cis-HomoaconitateChEBI
Homo-cis-aconitateChEBI
(Z)-1,2,4-But-1-enetricarboxylateGenerator
But-1-ene-1,2,4-tricarboxylic acidGenerator
cis-Homoaconitic acidGenerator
Homo-cis-aconitic acidGenerator
(Z)-But-1-ene-1,2,4-tricarboxylic acidGenerator
Molecular FormulaC7H8O6
Average Mass188.1348
Monoisotopic Mass188.032087988
IUPAC Name(1Z)-but-1-ene-1,2,4-tricarboxylic acid
Traditional Namehomo-cis-aconitate
CAS Registry NumberNot Available
SMILES
[H]\C(C(O)=O)=C(/CCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H8O6/c8-5(9)2-1-4(7(12)13)3-6(10)11/h3H,1-2H2,(H,8,9)(H,10,11)(H,12,13)/b4-3-
InChI KeyBJYPZFUWWJSAKC-ARJAWSKDSA-N