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Showing metabocard for Maleylacetoacetic acid (HMDB0002052)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2020-09-15 18:51:49 UTC
HMDB IDHMDB0002052
Secondary Accession Numbers
  • HMDB02052
Metabolite Identification
Common NameMaleylacetoacetic acid
DescriptionMaleylacetoacetic acid, also known as 4-maleylacetoacetate, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. Maleylacetoacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Maleylacetoacetic acid exists in all living organisms, ranging from bacteria to humans. Within humans, maleylacetoacetic acid participates in a number of enzymatic reactions. In particular, maleylacetoacetic acid can be converted into 4-fumarylacetoacetic acid through its interaction with the enzyme maleylacetoacetate isomerase. In addition, maleylacetoacetic acid can be biosynthesized from homogentisic acid; which is mediated by the enzyme homogentisate 1,2-dioxygenase. 4-Maleylacetoacetate (4-maleylacetoacetate) is an intermediate in the metabolism of tyrosine. In humans, maleylacetoacetic acid is involved in the metabolic disorder called tyrosinemia type I. Maleylacetoacetic acid is a potentially toxic compound.
Structure
Data?1600195909
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002052 (Maleylacetoacetic acid)


  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
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3D MOL for HMDB0002052 (Maleylacetoacetic acid)

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
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3D SDF for HMDB0002052 (Maleylacetoacetic acid)


  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>
HMDB0002052

> <DATABASE_NAME>
hmdb

> <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 HMDB0002052 (Maleylacetoacetic acid)

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
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PDB for HMDB0002052 (Maleylacetoacetic acid)

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
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3D PDB for HMDB0002052 (Maleylacetoacetic acid)

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
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SMILES for HMDB0002052 (Maleylacetoacetic acid)

OC(=O)CC(=O)CC(=O)\C=C/C(O)=O
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INCHI for HMDB0002052 (Maleylacetoacetic acid)

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-
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
4-MaleylacetoacetateChEBI
4-Maleylacetoacetic acidKegg
MaleylacetoacetateGenerator
(2Z)-4,6-Dioxo-2-octenedioic acidHMDB
Maleylacetoacetic acidHMDB
Chemical FormulaC8H8O6
Average Molecular Weight200.1455
Monoisotopic Molecular Weight200.032087988
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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Beta-keto acid
  • 1,3-diketone
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • Unsaturated fatty acid
  • 1,3-dicarbonyl compound
  • Fatty acyl
  • Enone
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.65 g/LALOGPS
logP-0.19ALOGPS
logP0.4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area108.74 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity44.4 m³·mol⁻¹ChemAxon
Polarizability16.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+138.69430932474
DeepCCS[M-H]-135.57130932474
DeepCCS[M-2H]-172.4630932474
DeepCCS[M+Na]+147.99930932474
AllCCS[M+H]+142.632859911
AllCCS[M+H-H2O]+138.832859911
AllCCS[M+NH4]+146.132859911
AllCCS[M+Na]+147.132859911
AllCCS[M-H]-138.732859911
AllCCS[M+Na-2H]-139.632859911
AllCCS[M+HCOO]-140.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Maleylacetoacetic acidOC(=O)CC(=O)CC(=O)\C=C/C(O)=O3350.7Standard polar33892256
Maleylacetoacetic acidOC(=O)CC(=O)CC(=O)\C=C/C(O)=O1412.1Standard non polar33892256
Maleylacetoacetic acidOC(=O)CC(=O)CC(=O)\C=C/C(O)=O1894.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Maleylacetoacetic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CC(=O)CC(=O)/C=C\C(=O)O1850.6Semi standard non polar33892256
Maleylacetoacetic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)CC(=O)O1810.5Semi standard non polar33892256
Maleylacetoacetic acid,1TMS,isomer #3C[Si](C)(C)OC(=CC(=O)/C=C\C(=O)O)CC(=O)O2029.7Semi standard non polar33892256
Maleylacetoacetic acid,1TMS,isomer #4C[Si](C)(C)OC(=CC(=O)O)CC(=O)/C=C\C(=O)O2001.7Semi standard non polar33892256
Maleylacetoacetic acid,1TMS,isomer #5C[Si](C)(C)OC(=CC(=O)CC(=O)O)/C=C\C(=O)O2028.1Semi standard non polar33892256
Maleylacetoacetic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)CC(=O)O[Si](C)(C)C1885.1Semi standard non polar33892256
Maleylacetoacetic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CC(=CC(=O)/C=C\C(=O)O)O[Si](C)(C)C2101.4Semi standard non polar33892256
Maleylacetoacetic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O)O[Si](C)(C)C2063.0Semi standard non polar33892256
Maleylacetoacetic acid,2TMS,isomer #4C[Si](C)(C)OC(=O)CC(=O)C=C(/C=C\C(=O)O)O[Si](C)(C)C2097.1Semi standard non polar33892256
Maleylacetoacetic acid,2TMS,isomer #5C[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O)O[Si](C)(C)C2114.4Semi standard non polar33892256
Maleylacetoacetic acid,2TMS,isomer #6C[Si](C)(C)OC(=O)/C=C\C(=O)CC(=CC(=O)O)O[Si](C)(C)C2055.0Semi standard non polar33892256
Maleylacetoacetic acid,2TMS,isomer #7C[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O)O[Si](C)(C)C2106.0Semi standard non polar33892256
Maleylacetoacetic acid,2TMS,isomer #8C[Si](C)(C)OC(=CC(=O)O)C=C(/C=C\C(=O)O)O[Si](C)(C)C2270.0Semi standard non polar33892256
Maleylacetoacetic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2137.1Semi standard non polar33892256
Maleylacetoacetic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1984.7Standard non polar33892256
Maleylacetoacetic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2195.5Standard polar33892256
Maleylacetoacetic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C2027.2Semi standard non polar33892256
Maleylacetoacetic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C1968.9Standard non polar33892256
Maleylacetoacetic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C2105.1Standard polar33892256
Maleylacetoacetic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2116.3Semi standard non polar33892256
Maleylacetoacetic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C1991.6Standard non polar33892256
Maleylacetoacetic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C2218.9Standard polar33892256
Maleylacetoacetic acid,3TMS,isomer #4C[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O)O[Si](C)(C)C)O[Si](C)(C)C2273.3Semi standard non polar33892256
Maleylacetoacetic acid,3TMS,isomer #4C[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O)O[Si](C)(C)C)O[Si](C)(C)C2099.8Standard non polar33892256
Maleylacetoacetic acid,3TMS,isomer #4C[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O)O[Si](C)(C)C)O[Si](C)(C)C2362.7Standard polar33892256
Maleylacetoacetic acid,3TMS,isomer #5C[Si](C)(C)OC(=O)/C=C\C(=CC(=CC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C2231.1Semi standard non polar33892256
Maleylacetoacetic acid,3TMS,isomer #5C[Si](C)(C)OC(=O)/C=C\C(=CC(=CC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C2062.5Standard non polar33892256
Maleylacetoacetic acid,3TMS,isomer #5C[Si](C)(C)OC(=O)/C=C\C(=CC(=CC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C2392.4Standard polar33892256
Maleylacetoacetic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2234.6Semi standard non polar33892256
Maleylacetoacetic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2121.2Standard non polar33892256
Maleylacetoacetic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2112.5Standard polar33892256
Maleylacetoacetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC(=O)CC(=O)/C=C\C(=O)O2091.2Semi standard non polar33892256
Maleylacetoacetic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)CC(=O)O2060.9Semi standard non polar33892256
Maleylacetoacetic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC(=O)/C=C\C(=O)O)CC(=O)O2267.6Semi standard non polar33892256
Maleylacetoacetic acid,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CC(=O)O)CC(=O)/C=C\C(=O)O2235.8Semi standard non polar33892256
Maleylacetoacetic acid,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=CC(=O)CC(=O)O)/C=C\C(=O)O2268.6Semi standard non polar33892256
Maleylacetoacetic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)CC(=O)O[Si](C)(C)C(C)(C)C2345.8Semi standard non polar33892256
Maleylacetoacetic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CC(=CC(=O)/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C2538.6Semi standard non polar33892256
Maleylacetoacetic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C2498.5Semi standard non polar33892256
Maleylacetoacetic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)CC(=O)C=C(/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C2538.3Semi standard non polar33892256
Maleylacetoacetic acid,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O)O[Si](C)(C)C(C)(C)C2590.8Semi standard non polar33892256
Maleylacetoacetic acid,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)CC(=CC(=O)O)O[Si](C)(C)C(C)(C)C2515.3Semi standard non polar33892256
Maleylacetoacetic acid,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O)O[Si](C)(C)C(C)(C)C2555.9Semi standard non polar33892256
Maleylacetoacetic acid,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)OC(=CC(=O)O)C=C(/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C2715.3Semi standard non polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2808.6Semi standard non polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2605.8Standard non polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2491.8Standard polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2659.1Semi standard non polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2597.4Standard non polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2418.9Standard polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2770.8Semi standard non polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2629.8Standard non polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2506.2Standard polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2929.7Semi standard non polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2679.9Standard non polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2613.7Standard polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=CC(=CC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2980.5Semi standard non polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=CC(=CC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2683.6Standard non polar33892256
Maleylacetoacetic acid,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=CC(=CC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2623.3Standard polar33892256
Maleylacetoacetic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3121.7Semi standard non polar33892256
Maleylacetoacetic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2844.0Standard non polar33892256
Maleylacetoacetic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2498.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Maleylacetoacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9300000000-7b2ae90eb353073cb6522017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maleylacetoacetic acid GC-MS (2 TMS) - 70eV, Positivesplash10-05bu-7092000000-254fb0c9b4683fd48ef12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Maleylacetoacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 10V, Positive-QTOFsplash10-0fsi-1920000000-f36f976fb4a0271e936b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 20V, Positive-QTOFsplash10-000i-6900000000-692cbcc9f99aac913e422016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 40V, Positive-QTOFsplash10-00rj-9200000000-8e21be4180492b988f542016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 10V, Negative-QTOFsplash10-0a4j-1900000000-ea634f49698a94be63112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 20V, Negative-QTOFsplash10-0a4i-5900000000-4d5261faac7c9dc29c362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 40V, Negative-QTOFsplash10-0a4i-9500000000-17b0a81ad882f626ac2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 10V, Positive-QTOFsplash10-001r-4900000000-80aa92977bd40f96e7402021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 20V, Positive-QTOFsplash10-00kb-9100000000-7d688d7f7d7a804690a32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 40V, Positive-QTOFsplash10-0006-9000000000-c0d2eba6487ff950c63d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 10V, Negative-QTOFsplash10-0bt9-3900000000-0353447aa417ab1cef292021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 20V, Negative-QTOFsplash10-014i-9600000000-fabbd099eded8f7879a92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Maleylacetoacetic acid 40V, Negative-QTOFsplash10-014i-9000000000-e4bd7674e02d56b3573f2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022817
KNApSAcK IDC00007508
Chemspider ID4444078
KEGG Compound IDC01036
BioCyc ID4-MALEYL-ACETOACETATE
BiGG ID1485279
Wikipedia Link4-Maleylacetoacetic_acid
METLIN ID6462
PubChem Compound5280393
PDB IDNot Available
ChEBI ID47904
Food Biomarker OntologyNot Available
VMH ID4MLACAC
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kvittingen EA, Halvorsen S, Jellum E: Deficient fumarylacetoacetate fumarylhydrolase activity in lymphocytes and fibroblasts from patients with hereditary tyrosinemia. Pediatr Res. 1983 Jul;17(7):541-4. [PubMed:6622096 ]
  2. Gray RG, Patrick AD, Preston FE, Whitfield MF: Acute hereditary tyrosinaemia type I: clinical, biochemical and haematological studies in twins. J Inherit Metab Dis. 1981;4(1):37-40. [PubMed:6785523 ]

Enzymes

Enzyme Details
1. Maleylacetoacetate isomerase
General function:
Involved in catalytic activity
Specific function:
Bifunctional enzyme showing minimal glutathione-conjugating activity with ethacrynic acid and 7-chloro-4-nitrobenz-2-oxa-1,3-diazole and maleylacetoacetate isomerase activity. Has also low glutathione peroxidase activity with T-butyl and cumene hydroperoxides. Is able to catalyze the glutathione dependent oxygenation of dichloroacetic acid to glyoxylic acid.
Gene Name:
GSTZ1
Uniprot ID:
O43708
Molecular weight:
17895.68
Reactions
Maleylacetoacetic acid → 4-Fumarylacetoacetic aciddetails
Enzyme Details
2. Homogentisate 1,2-dioxygenase
General function:
Involved in homogentisate 1,2-dioxygenase activity
Specific function:
Not Available
Gene Name:
HGD
Uniprot ID:
Q93099
Molecular weight:
49963.41
Reactions
Homogentisic acid + Oxygen → Maleylacetoacetic aciddetails