Showing metabocard for 4-Fumarylacetoacetic acid (BMDB0001268)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:43:21 UTC
Update Date2020-05-21 16:28:38 UTC
BMDB IDBMDB0001268
Secondary Accession Numbers
  • BMDB01268
Metabolite Identification
Common Name4-Fumarylacetoacetic acid
Description4-Fumarylacetoacetic acid, also known as fumarylacetoacetate, 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. In cattle, 4-fumarylacetoacetic acid is involved in the metabolic pathway called the phenylalanine and tyrosine metabolism pathway. Based on a literature review very few articles have been published on 4-Fumarylacetoacetic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
FumarylacetoacetoneChEBI
FumarylacetoacetateKegg
Fumarylacetoacetic acidGenerator
4-FumarylacetoacetateGenerator
4-Fumaryl-acetoacetateHMDB
(2E)-4,6-Dioxo-2-octenedioic acidHMDB
4-Fumarylacetoacetic acidHMDB
Chemical FormulaC8H8O6
Average Molecular Weight200.1455
Monoisotopic Molecular Weight200.032087988
IUPAC Name(2E)-4,6-dioxooct-2-enedioic acid
Traditional Name4-fumarylacetoacetic acid
CAS Registry Number28613-33-4
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-OWOJBTEDSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.19ALOGPS
logP0.4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
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
Polarizability17.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9300000000-7b2ae90eb353073cb652View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05bu-7092000000-254fb0c9b4683fd48ef1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsi-1920000000-f36f976fb4a0271e936bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-6900000000-692cbcc9f99aac913e42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rj-9200000000-8e21be4180492b988f54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-1900000000-ea634f49698a94be6311View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5900000000-4d5261faac7c9dc29c36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-17b0a81ad882f626ac2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-3900000000-0353447aa417ab1cef29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9600000000-fabbd099eded8f7879a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-e4bd7674e02d56b3573fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-4900000000-80aa92977bd40f96e740View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-9100000000-7d688d7f7d7a804690a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c0d2eba6487ff950c63dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001268
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022817
KNApSAcK IDC00007599
Chemspider ID4444081
KEGG Compound IDC01061
BioCyc ID4-FUMARYL-ACETOACETATE
BiGG ID1485275
Wikipedia LinkFumarylacetoacetic_acid
METLIN ID6123
PubChem Compound5280398
PDB IDNot Available
ChEBI ID30907
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Fumarylacetoacetase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Not Available
Gene Name:
FAH
Uniprot ID:
A5PKH3
Molecular weight:
46156.0
Reactions
4-Fumarylacetoacetic acid + Water → Acetoacetic acid + Fumaric aciddetails
Enzyme Details
2. Glutathione S-transferase zeta 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
GSTZ1
Uniprot ID:
Q2KIM6
Molecular weight:
24113.0
Reactions
Maleylacetoacetic acid → 4-Fumarylacetoacetic aciddetails