MiMeDB: Showing metabocard for Maleylacetoacetic acid (MMDBc0047937)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:16:52 UTC

Update Date

2024-04-30 20:33:01 UTC

Metabolite ID

MMDBc0047937

Metabolite Identification

Common Name

Maleylacetoacetic acid

Description

Maleylacetoacetic 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

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>
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

$$$$

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

Synonyms

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

Molecular Formula

C₈H₈O₆

Average Mass

200.1455

Monoisotopic Mass

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 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9300000000-7b2ae90eb353073cb652	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05bu-7092000000-254fb0c9b4683fd48ef1	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fsi-1920000000-f36f976fb4a0271e936b	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-6900000000-692cbcc9f99aac913e42	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00rj-9200000000-8e21be4180492b988f54	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4j-1900000000-ea634f49698a94be6311	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-5900000000-4d5261faac7c9dc29c36	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9500000000-17b0a81ad882f626ac2a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001r-4900000000-80aa92977bd40f96e740	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-9100000000-7d688d7f7d7a804690a3	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c0d2eba6487ff950c63d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-3900000000-0353447aa417ab1cef29	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9600000000-fabbd099eded8f7879a9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-e4bd7674e02d56b3573f	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192437	Maleylacetoacetate isomerase	Enzyme	O43708	Homo sapiens
MMDBp0192462	Homogentisate 1,2-dioxygenase	Unknown	Q93099	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001435	Homogentisic acid	Maleylacetoacetic acid	Not Available	VMH; KEGG	30371894
MMDBr0001606	Maleylacetoacetic acid	4-Fumarylacetoacetic acid	Not Available	VMH; KEGG	30371894
MMDBr0008560	Maleylacetoacetic acid	Succinyl-Acetoacetate	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	114	Human feces; Human sputum; Human ; Human pleural fluid plaque; Turkey	Metabolic reconstruction
Bacteria	Firmicutes	14	Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	14	Human feces; Human	Metabolic reconstruction
Bacteria	Bacteroidetes	4	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0002052

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

References

Synthesis Reference

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. doi: 10.1203/00006450-198307000-00005. [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. doi: 10.1007/BF02263580. [PubMed:6785523 ]

Showing metabocard for Maleylacetoacetic acid (MMDBc0047937)

MOL for #<Metabolite:0x00007fdb04574248>

3D MOL for #<Metabolite:0x00007fdb04574248>

3D SDF for #<Metabolite:0x00007fdb04574248>

3D-SDF for #<Metabolite:0x00007fdb04574248>

PDB for #<Metabolite:0x00007fdb04574248>

3D PDB for #<Metabolite:0x00007fdb04574248>

SMILES for #<Metabolite:0x00007fdb04574248>

INCHI for #<Metabolite:0x00007fdb04574248>

Structure for #<Metabolite:0x00007fdb04574248>

3D Structure for #<Metabolite:0x00007fdb04574248>