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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:34 UTC

Update Date

2020-09-15 18:51:49 UTC

HMDB ID

HMDB0002052

Secondary Accession Numbers

HMDB02052

Metabolite Identification

Common Name

Maleylacetoacetic acid

Description

Maleylacetoacetic 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  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

$$$$

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Maleylacetoacetate	ChEBI
4-Maleylacetoacetic acid	Kegg
Maleylacetoacetate	Generator
(2Z)-4,6-Dioxo-2-octenedioic acid	HMDB
Maleylacetoacetic acid	HMDB

Chemical Formula

C₈H₈O₆

Average Molecular Weight

200.1455

Monoisotopic Molecular Weight

200.032087988

IUPAC Name

(2Z)-4,6-dioxooct-2-enedioic acid

Traditional Name

maleylacetoacetic acid

CAS Registry Number

5698-52-2

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 Key

GACSIVHAIFQKTC-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

oxo dicarboxylic acid (CHEBI:47904 )
beta-diketone (CHEBI:47904 )
Dicarboxylic acids (LMFA01170114 )

Ontology

Physiological effect

Adverse health effect

Genetic disorder

Inborn errors of metabolism

Alkaptonuria (PMID: 25956497 )

Hawkinsinuria (PMID: 10412819 , PMID: 11281457 , PMID: 11978597 , +3

Source	Link
Pubmed	PMID: 10412819
Pubmed	PMID: 11281457
Pubmed	PMID: 11978597
Pubmed	PMID: 25754623
Pubmed	PMID: 26226126
Pubmed	PMID: 26226126

)

Phenylketonuria (PMID: 24023812 , PMID: 6321058 , PMID: 20971021 , +55

Source	Link
Pubmed	PMID: 24023812
Pubmed	PMID: 6321058
Pubmed	PMID: 20971021
Pubmed	PMID: 20573794
Pubmed	PMID: 23657156
Pubmed	PMID: 22800120
Pubmed	PMID: 21389975
Pubmed	PMID: 27012787
Pubmed	PMID: 9625050
Pubmed	PMID: 15740018
Pubmed	PMID: 12663291
Pubmed	PMID: 2702744
Pubmed	PMID: 16939360
Pubmed	PMID: 17474139
Pubmed	PMID: 15992788
Pubmed	PMID: 22827565
Pubmed	PMID: 22148915
Pubmed	PMID: 21388201
Pubmed	PMID: 22932811
Pubmed	PMID: 19551947
Pubmed	PMID: 31775291
Pubmed	PMID: 2026685
Pubmed	PMID: 4434100
Pubmed	PMID: 28853722
Pubmed	PMID: 19033659
Pubmed	PMID: 23430553
Pubmed	PMID: 3168222
Pubmed	PMID: 19468821
Pubmed	PMID: 31506554
Pubmed	PMID: 2116554
Pubmed	PMID: 19309105
Pubmed	PMID: 25536744
Pubmed	PMID: 4903899
Pubmed	PMID: 14708889
Pubmed	PMID: 8087979
Pubmed	PMID: 4837567
Pubmed	PMID: 2091926
Pubmed	PMID: 17022649
Pubmed	PMID: 32966057
Pubmed	PMID: 15651030
Pubmed	PMID: 24909877
Pubmed	PMID: 6790852
Pubmed	PMID: 4837567
Pubmed	PMID: 15168722
Pubmed	PMID: 7320149
Pubmed	PMID: 25012580
Pubmed	PMID: 25213569
Pubmed	PMID: 466810
Pubmed	PMID: 9686366
Pubmed	PMID: 25754623
Pubmed	PMID: 12101068
Pubmed	PMID: 19217890
Pubmed	PMID: 10102904
Pubmed	PMID: 9732980
Pubmed	PMID: 8178819
Pubmed	PMID: 16789974
Pubmed	PMID: 3873535
Pubmed	PMID: 30830347

)

Tyrosinemia

Disposition

Biological location

Cellular substructure

Cytoplasm

Green lentil

Other pulses

Peas

Lentils

Lentils

Onion-family vegetables

Herb and spice mixtures

Curry powder

Cereals and cereal products

Cereals

Cereal products

Doughs

Sourdough

Leavened breads

Flat breads

Other breads

Potato bread

Sweet breads

Raisin bread

Teas

Herbal tea

Herbal teas

Taco shell
Tostada shell

Horse

Lagomorphs

Ovis

Sheep (Mutton, Lamb)

Caprae

Domestic goat

Coffee and coffee products

Coffee

Soy

Soy products

Soy bean

Baking goods

Wrappers

Wonton wrapper

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.65 g/L	ALOGPS
logP	-0.19	ALOGPS
logP	0.4	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.74 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	44.4 m³·mol⁻¹	ChemAxon
Polarizability	16.75 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	138.694	30932474
DeepCCS	[M-H]-	135.571	30932474
DeepCCS	[M-2H]-	172.46	30932474
DeepCCS	[M+Na]+	147.999	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Maleylacetoacetic acid	OC(=O)CC(=O)CC(=O)\C=C/C(O)=O	3350.7	Standard polar	33892256
Maleylacetoacetic acid	OC(=O)CC(=O)CC(=O)\C=C/C(O)=O	1412.1	Standard non polar	33892256
Maleylacetoacetic acid	OC(=O)CC(=O)CC(=O)\C=C/C(O)=O	1894.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Maleylacetoacetic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC(=O)CC(=O)/C=C\C(=O)O	1850.6	Semi standard non polar	33892256
Maleylacetoacetic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)CC(=O)O	1810.5	Semi standard non polar	33892256
Maleylacetoacetic acid,1TMS,isomer #3	C[Si](C)(C)OC(=CC(=O)/C=C\C(=O)O)CC(=O)O	2029.7	Semi standard non polar	33892256
Maleylacetoacetic acid,1TMS,isomer #4	C[Si](C)(C)OC(=CC(=O)O)CC(=O)/C=C\C(=O)O	2001.7	Semi standard non polar	33892256
Maleylacetoacetic acid,1TMS,isomer #5	C[Si](C)(C)OC(=CC(=O)CC(=O)O)/C=C\C(=O)O	2028.1	Semi standard non polar	33892256
Maleylacetoacetic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)CC(=O)O[Si](C)(C)C	1885.1	Semi standard non polar	33892256
Maleylacetoacetic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC(=CC(=O)/C=C\C(=O)O)O[Si](C)(C)C	2101.4	Semi standard non polar	33892256
Maleylacetoacetic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O)O[Si](C)(C)C	2063.0	Semi standard non polar	33892256
Maleylacetoacetic acid,2TMS,isomer #4	C[Si](C)(C)OC(=O)CC(=O)C=C(/C=C\C(=O)O)O[Si](C)(C)C	2097.1	Semi standard non polar	33892256
Maleylacetoacetic acid,2TMS,isomer #5	C[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O)O[Si](C)(C)C	2114.4	Semi standard non polar	33892256
Maleylacetoacetic acid,2TMS,isomer #6	C[Si](C)(C)OC(=O)/C=C\C(=O)CC(=CC(=O)O)O[Si](C)(C)C	2055.0	Semi standard non polar	33892256
Maleylacetoacetic acid,2TMS,isomer #7	C[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O)O[Si](C)(C)C	2106.0	Semi standard non polar	33892256
Maleylacetoacetic acid,2TMS,isomer #8	C[Si](C)(C)OC(=CC(=O)O)C=C(/C=C\C(=O)O)O[Si](C)(C)C	2270.0	Semi standard non polar	33892256
Maleylacetoacetic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2137.1	Semi standard non polar	33892256
Maleylacetoacetic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1984.7	Standard non polar	33892256
Maleylacetoacetic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2195.5	Standard polar	33892256
Maleylacetoacetic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2027.2	Semi standard non polar	33892256
Maleylacetoacetic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1968.9	Standard non polar	33892256
Maleylacetoacetic acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C	2105.1	Standard polar	33892256
Maleylacetoacetic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2116.3	Semi standard non polar	33892256
Maleylacetoacetic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1991.6	Standard non polar	33892256
Maleylacetoacetic acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	2218.9	Standard polar	33892256
Maleylacetoacetic acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2273.3	Semi standard non polar	33892256
Maleylacetoacetic acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2099.8	Standard non polar	33892256
Maleylacetoacetic acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)C=C(C=C(/C=C\C(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2362.7	Standard polar	33892256
Maleylacetoacetic acid,3TMS,isomer #5	C[Si](C)(C)OC(=O)/C=C\C(=CC(=CC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2231.1	Semi standard non polar	33892256
Maleylacetoacetic acid,3TMS,isomer #5	C[Si](C)(C)OC(=O)/C=C\C(=CC(=CC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2062.5	Standard non polar	33892256
Maleylacetoacetic acid,3TMS,isomer #5	C[Si](C)(C)OC(=O)/C=C\C(=CC(=CC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2392.4	Standard polar	33892256
Maleylacetoacetic acid,4TMS,isomer #1	C[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)C	2234.6	Semi standard non polar	33892256
Maleylacetoacetic acid,4TMS,isomer #1	C[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)C	2121.2	Standard non polar	33892256
Maleylacetoacetic acid,4TMS,isomer #1	C[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)C	2112.5	Standard polar	33892256
Maleylacetoacetic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)CC(=O)/C=C\C(=O)O	2091.2	Semi standard non polar	33892256
Maleylacetoacetic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)CC(=O)O	2060.9	Semi standard non polar	33892256
Maleylacetoacetic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=CC(=O)/C=C\C(=O)O)CC(=O)O	2267.6	Semi standard non polar	33892256
Maleylacetoacetic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=CC(=O)O)CC(=O)/C=C\C(=O)O	2235.8	Semi standard non polar	33892256
Maleylacetoacetic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=CC(=O)CC(=O)O)/C=C\C(=O)O	2268.6	Semi standard non polar	33892256
Maleylacetoacetic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)CC(=O)O[Si](C)(C)C(C)(C)C	2345.8	Semi standard non polar	33892256
Maleylacetoacetic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC(=CC(=O)/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C	2538.6	Semi standard non polar	33892256
Maleylacetoacetic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C=C(CC(=O)/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C	2498.5	Semi standard non polar	33892256
Maleylacetoacetic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)C=C(/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C	2538.3	Semi standard non polar	33892256
Maleylacetoacetic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=CC(=O)CC(=O)O)O[Si](C)(C)C(C)(C)C	2590.8	Semi standard non polar	33892256
Maleylacetoacetic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)CC(=CC(=O)O)O[Si](C)(C)C(C)(C)C	2515.3	Semi standard non polar	33892256
Maleylacetoacetic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)C=C(CC(=O)O)O[Si](C)(C)C(C)(C)C	2555.9	Semi standard non polar	33892256
Maleylacetoacetic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=CC(=O)O)C=C(/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C	2715.3	Semi standard non polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #1	CC(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)C	2808.6	Semi standard non polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #1	CC(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)C	2605.8	Standard non polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #1	CC(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)C	2491.8	Standard polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #2	CC(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)C	2659.1	Semi standard non polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #2	CC(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)C	2597.4	Standard non polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #2	CC(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)C	2418.9	Standard polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #3	CC(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)C	2770.8	Semi standard non polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #3	CC(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)C	2629.8	Standard non polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #3	CC(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)C	2506.2	Standard polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #4	CC(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)C	2929.7	Semi standard non polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #4	CC(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)C	2679.9	Standard non polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #4	CC(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)C	2613.7	Standard polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #5	CC(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)C	2980.5	Semi standard non polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #5	CC(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)C	2683.6	Standard non polar	33892256
Maleylacetoacetic acid,3TBDMS,isomer #5	CC(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)C	2623.3	Standard polar	33892256
Maleylacetoacetic acid,4TBDMS,isomer #1	CC(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)C	3121.7	Semi standard non polar	33892256
Maleylacetoacetic acid,4TBDMS,isomer #1	CC(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)C	2844.0	Standard non polar	33892256
Maleylacetoacetic acid,4TBDMS,isomer #1	CC(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)C	2498.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Maleylacetoacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9300000000-7b2ae90eb353073cb652	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Maleylacetoacetic acid GC-MS (2 TMS) - 70eV, Positive	splash10-05bu-7092000000-254fb0c9b4683fd48ef1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Maleylacetoacetic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 10V, Positive-QTOF	splash10-0fsi-1920000000-f36f976fb4a0271e936b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 20V, Positive-QTOF	splash10-000i-6900000000-692cbcc9f99aac913e42	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 40V, Positive-QTOF	splash10-00rj-9200000000-8e21be4180492b988f54	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 10V, Negative-QTOF	splash10-0a4j-1900000000-ea634f49698a94be6311	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 20V, Negative-QTOF	splash10-0a4i-5900000000-4d5261faac7c9dc29c36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 40V, Negative-QTOF	splash10-0a4i-9500000000-17b0a81ad882f626ac2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 10V, Positive-QTOF	splash10-001r-4900000000-80aa92977bd40f96e740	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 20V, Positive-QTOF	splash10-00kb-9100000000-7d688d7f7d7a804690a3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 40V, Positive-QTOF	splash10-0006-9000000000-c0d2eba6487ff950c63d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 10V, Negative-QTOF	splash10-0bt9-3900000000-0353447aa417ab1cef29	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 20V, Negative-QTOF	splash10-014i-9600000000-fabbd099eded8f7879a9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Maleylacetoacetic acid 40V, Negative-QTOF	splash10-014i-9000000000-e4bd7674e02d56b3573f	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Phenylalanine and Tyrosine Metabolism
Phenylketonuria		Not Available
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)		Not Available
Tyrosinemia Type 3 (TYRO3)		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

4-MALEYL-ACETOACETATE

BiGG ID

1485279

Wikipedia Link

4-Maleylacetoacetic_acid

METLIN ID

6462

PubChem Compound

5280393

PDB ID

Not Available

ChEBI ID

47904

Food Biomarker Ontology

Not Available

VMH ID

4MLACAC

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 acid	details

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 acid	details

Showing metabocard for Maleylacetoacetic acid (HMDB0002052)

MOL for HMDB0002052 (Maleylacetoacetic acid)

3D MOL for HMDB0002052 (Maleylacetoacetic acid)

3D SDF for HMDB0002052 (Maleylacetoacetic acid)

3D-SDF for HMDB0002052 (Maleylacetoacetic acid)

PDB for HMDB0002052 (Maleylacetoacetic acid)

3D PDB for HMDB0002052 (Maleylacetoacetic acid)

SMILES for HMDB0002052 (Maleylacetoacetic acid)

INCHI for HMDB0002052 (Maleylacetoacetic acid)

Structure for HMDB0002052 (Maleylacetoacetic acid)

3D Structure for HMDB0002052 (Maleylacetoacetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions