Showing metabocard for 2-Maleylacetate (MMDBc0029976)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:49:05 UTC
Update Date2024-04-30 19:43:50 UTC
Metabolite IDMMDBc0029976
Metabolite Identification
Common Name2-Maleylacetate
Description2-maleylacetate belongs to the class of Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. (inferred from compound structure)

2-Maleylacetate is involved in the degradation pathway of aromatic compounds. Reduction of the double bond in maleylacetate is catalyzed by the enzyme maleylacetate reductase, which was also purified from E. coli (PMID 8900023 )
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9251237798>

 
  Mrv0541 02241222152D          
 
 11 10  0  0  0  0            999 V2000
   16.3088  -10.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5950  -10.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0263  -10.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3088  -11.6298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5950   -9.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7400  -10.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3088   -9.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4538  -10.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7400  -11.6298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3088   -8.3269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0225   -9.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9251237798>

HMDB0060348
     RDKit          3D
2-Maleylacetate
 17 16  0  0  0  0  0  0  0  0999 V2000
    0.8225    1.2857   -0.9636 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6973    0.7729   -0.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9025    1.5392   -0.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7744   -0.4089    0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -1.2583    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4739   -1.2828    0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1264   -2.3649    0.5629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3147   -0.4986   -0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0098    0.5516    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888    0.6134    1.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8939    1.4682   -0.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    1.2882   -0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7662   -0.6188    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1202   -2.1364    1.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2326   -1.1935   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -0.1889   -1.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7804    2.4319   -0.2706 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  8 15  1  0
  8 16  1  0
 11 17  1  0
M  END
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3D SDF for #<Metabolite:0x00007f9251237798>

 
  Mrv0541 02241222152D          
 
 11 10  0  0  0  0            999 V2000
   16.3088  -10.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5950  -10.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0263  -10.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3088  -11.6298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5950   -9.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7400  -10.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3088   -9.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4538  -10.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7400  -11.6298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3088   -8.3269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0225   -9.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  2  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  2  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029976

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-2H,3H2,(H,8,9)(H,10,11)/b2-1-

> <INCHI_KEY>
SOXXPQLIZIPMIZ-UPHRSURJSA-N

> <FORMULA>
C6H6O5

> <MOLECULAR_WEIGHT>
158.1088

> <EXACT_MASS>
158.021523302

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
13.163660048682335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-4-oxohex-2-enedioic acid

> <ALOGPS_LOGP>
-0.06

> <JCHEM_LOGP>
0.1809396373333333

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.852909078950445

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7117673431117693

> <JCHEM_PKA_STRONGEST_BASIC>
-7.230072909210429

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
34.5022

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
maleylacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9251237798>

HMDB0060348
     RDKit          3D
2-Maleylacetate
 17 16  0  0  0  0  0  0  0  0999 V2000
    0.8225    1.2857   -0.9636 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6973    0.7729   -0.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9025    1.5392   -0.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7744   -0.4089    0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8229   -1.2583    0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4739   -1.2828    0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1264   -2.3649    0.5629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3147   -0.4986   -0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0098    0.5516    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888    0.6134    1.2693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8939    1.4682   -0.5284 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6464    1.2882   -0.9251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7662   -0.6188    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1202   -2.1364    1.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2326   -1.1935   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9320   -0.1889   -1.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7804    2.4319   -0.2706 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  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  4 13  1  0
  5 14  1  0
  8 15  1  0
  8 16  1  0
 11 17  1  0
M  END
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PDB for #<Metabolite:0x00007f9251237798>

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      30.443 -20.164   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.111 -19.392   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.782 -19.392   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      30.443 -21.709   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      29.111 -17.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.115 -20.164   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.443 -17.081   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      34.447 -19.392   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      33.115 -21.709   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      30.443 -15.544   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      31.775 -17.861   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1                                                            
CONECT    5    2    7                                                       
CONECT    6    3    8    9                                                  
CONECT    7    5   10   11                                                  
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for #<Metabolite:0x00007f9251237798>

COMPND    HMDB0060348
HETATM    1  O1  UNL     1       0.822   1.286  -0.964  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.697   0.773  -0.286  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.903   1.539  -0.284  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.774  -0.409   0.492  1.00  0.00           C  
HETATM    5  C3  UNL     1       0.823  -1.258   0.637  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.474  -1.283   0.116  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.126  -2.365   0.563  1.00  0.00           O  
HETATM    8  C5  UNL     1      -1.315  -0.499  -0.754  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.010   0.552   0.037  1.00  0.00           C  
HETATM   10  O4  UNL     1      -1.789   0.613   1.269  1.00  0.00           O  
HETATM   11  O5  UNL     1      -2.894   1.468  -0.528  1.00  0.00           O  
HETATM   12  H1  UNL     1       3.646   1.288  -0.925  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.766  -0.619   1.033  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.120  -2.136   1.317  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.233  -1.194  -1.025  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.932  -0.189  -1.726  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.780   2.432  -0.271  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    5   13
CONECT    5    6   14
CONECT    6    7    7    8
CONECT    8    9   15   16
CONECT    9   10   10   11
CONECT   11   17
END
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SMILES for #<Metabolite:0x00007f9251237798>

OC(=O)CC(=O)\C=C/C(O)=O
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INCHI for #<Metabolite:0x00007f9251237798>

InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-2H,3H2,(H,8,9)(H,10,11)/b2-1-
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Synonyms
ValueSource
(Z)-4-oxo-2-Hexenedioic acidChEBI
4-Oxohex-2-enedioateChEBI
MaleylacetateChEBI
(Z)-4-oxo-2-HexenedioateGenerator
4-Oxohex-2-enedioic acidGenerator
Maleylacetic acidGenerator
2-Maleylacetic acidGenerator
Maleoylacetic acidMeSH
Molecular FormulaC6H6O5
Average Mass158.1088
Monoisotopic Mass158.021523302
IUPAC Name(2Z)-4-oxohex-2-enedioic acid
Traditional Namemaleylacetic acid
CAS Registry Number24740-88-3
SMILES
OC(=O)CC(=O)\C=C/C(O)=O
InChI Identifier
InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-2H,3H2,(H,8,9)(H,10,11)/b2-1-
InChI KeySOXXPQLIZIPMIZ-UPHRSURJSA-N