Showing metabocard for Maleylacetoacetic acid (MMDBc0047937)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:16:52 UTC
Update Date2024-04-30 20:33:01 UTC
Metabolite IDMMDBc0047937
Metabolite Identification
Common NameMaleylacetoacetic acid
DescriptionMaleylacetoacetic acid, also known as 4-maleylacetoacetate, is an intermediate in the metabolism of tyrosine. Homogentisate 1,2-dioxygenase (HGD) is the enzyme which catalyzes the conversion of homogentisate into 4-maleylacetoacetate. HGD is involved in the catabolism of aromatic rings, more specifically in the breakdown of the amino acids tyrosine and phenylalanine.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f923b671450>


  Mrv1652309042000262D          

 14 13  0  0  0  0            999 V2000
10006.008110004.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.292610004.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.578210004.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.863510004.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.038110004.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.323510004.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.608810004.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.323510005.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.578210005.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.721510004.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.436910004.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.152510004.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.436910005.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.008110005.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  1 14  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f923b671450>

HMDB0002052
     RDKit          3D
Maleylacetoacetic acid
 22 21  0  0  0  0  0  0  0  0999 V2000
   -5.0411    1.0363   -0.3222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8439    0.6888    0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6155    0.7489    1.4197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9700    0.2980   -0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7274   -0.0822   -0.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -0.1783    0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4353    0.0800    1.5560 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4026   -0.6601    0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    0.4704   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    1.5845   -0.2946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    0.4343   -0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3924   -0.7883    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7785   -1.7357    0.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540   -0.9020   -0.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1557    0.1733    2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630    0.3184   -2.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2143   -0.3456   -1.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -1.0932    1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122   -1.5114   -0.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9248    0.6968   -1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401    1.2763    0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2126   -0.5091   -0.9200 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
 11 12  1  0
 12 13  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
  8 19  1  0
 11 20  1  0
 11 21  1  0
 14 22  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f923b671450>


  Mrv1652309042000262D          

 14 13  0  0  0  0            999 V2000
10006.008110004.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.292610004.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.578210004.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.863510004.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.038110004.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.323510004.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.608810004.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.323510005.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.578210005.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.721510004.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.436910004.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.152510004.2472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.436910005.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.008110005.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  1 14  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047937

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1-

> <INCHI_KEY>
GACSIVHAIFQKTC-UPHRSURJSA-N

> <FORMULA>
C8H8O6

> <MOLECULAR_WEIGHT>
200.1455

> <EXACT_MASS>
200.032087988

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.75405859034148

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-4,6-dioxooct-2-enedioic acid

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
0.4027936060000003

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.8248983902309295

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.716169602537572

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0576341820437145

> <JCHEM_POLAR_SURFACE_AREA>
108.74000000000001

> <JCHEM_REFRACTIVITY>
44.397400000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
maleylacetoacetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f923b671450>

HMDB0002052
     RDKit          3D
Maleylacetoacetic acid
 22 21  0  0  0  0  0  0  0  0999 V2000
   -5.0411    1.0363   -0.3222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8439    0.6888    0.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6155    0.7489    1.4197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9700    0.2980   -0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7274   -0.0822   -0.8093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261   -0.1783    0.4338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4353    0.0800    1.5560 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4026   -0.6601    0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    0.4704   -0.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    1.5845   -0.2946 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7085    0.4343   -0.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3924   -0.7883    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7785   -1.7357    0.6350 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7540   -0.9020   -0.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1557    0.1733    2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630    0.3184   -2.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2143   -0.3456   -1.7682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -1.0932    1.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4122   -1.5114   -0.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9248    0.6968   -1.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1401    1.2763    0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2126   -0.5091   -0.9200 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
 11 12  1  0
 12 13  2  0
 12 14  1  0
  3 15  1  0
  4 16  1  0
  5 17  1  0
  8 18  1  0
  8 19  1  0
 11 20  1  0
 11 21  1  0
 14 22  1  0
M  END
Download

PDB for #<Metabolite:0x00007f923b671450>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8677.8828675.363   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8676.5468674.595   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8675.2138675.363   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8673.8798674.595   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8672.3388674.595   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8671.0048675.363   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8669.6708674.595   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8671.0048676.904   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8675.2138676.904   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8679.2138674.595   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8680.5498675.363   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0    8681.8858674.595   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8680.5498676.904   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8677.8828676.904   0.000  0.00  0.00           O+0
CONECT    1    2   10   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END
Download

3D PDB for #<Metabolite:0x00007f923b671450>

COMPND    HMDB0002052
HETATM    1  O1  UNL     1      -5.041   1.036  -0.322  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.844   0.689   0.070  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.616   0.749   1.420  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.970   0.298  -0.996  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.727  -0.082  -0.809  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.026  -0.178   0.434  1.00  0.00           C  
HETATM    7  O3  UNL     1      -1.435   0.080   1.556  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.403  -0.660   0.344  1.00  0.00           C  
HETATM    9  C6  UNL     1       1.256   0.470  -0.081  1.00  0.00           C  
HETATM   10  O4  UNL     1       0.742   1.585  -0.295  1.00  0.00           O  
HETATM   11  C7  UNL     1       2.709   0.434  -0.293  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.392  -0.788   0.112  1.00  0.00           C  
HETATM   13  O5  UNL     1       2.779  -1.736   0.635  1.00  0.00           O  
HETATM   14  O6  UNL     1       4.754  -0.902  -0.091  1.00  0.00           O  
HETATM   15  H1  UNL     1      -4.156   0.173   2.064  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.363   0.318  -2.037  1.00  0.00           H  
HETATM   17  H3  UNL     1      -1.214  -0.346  -1.768  1.00  0.00           H  
HETATM   18  H4  UNL     1       0.669  -1.093   1.315  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.412  -1.511  -0.400  1.00  0.00           H  
HETATM   20  H6  UNL     1       2.925   0.697  -1.355  1.00  0.00           H  
HETATM   21  H7  UNL     1       3.140   1.276   0.318  1.00  0.00           H  
HETATM   22  H8  UNL     1       5.213  -0.509  -0.920  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   15
CONECT    4    5    5   16
CONECT    5    6   17
CONECT    6    7    7    8
CONECT    8    9   18   19
CONECT    9   10   10   11
CONECT   11   12   20   21
CONECT   12   13   13   14
CONECT   14   22
END
Download

SMILES for #<Metabolite:0x00007f923b671450>

OC(=O)CC(=O)CC(=O)\C=C/C(O)=O
Download

INCHI for #<Metabolite:0x00007f923b671450>

InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1-
Download
Synonyms
ValueSource
4-MaleylacetoacetateChEBI
4-Maleylacetoacetic acidKegg
MaleylacetoacetateGenerator
(2Z)-4,6-Dioxo-2-octenedioic acidHMDB
Maleylacetoacetic acidHMDB
Molecular FormulaC8H8O6
Average Mass200.1455
Monoisotopic Mass200.032087988
IUPAC Name(2Z)-4,6-dioxooct-2-enedioic acid
Traditional Namemaleylacetoacetic acid
CAS Registry Number5698-52-2
SMILES
OC(=O)CC(=O)CC(=O)\C=C/C(O)=O
InChI Identifier
InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1-
InChI KeyGACSIVHAIFQKTC-UPHRSURJSA-N