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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:08 UTC
HMDB IDHMDB0001268
Secondary Accession Numbers
  • HMDB0001428
  • HMDB01268
  • HMDB01428
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 humans, 4-fumarylacetoacetic acid is involved in the metabolic disorder called tyrosinemia type 3 (tyro3). 4-Fumarylacetoacetic acid has been detected, but not quantified in, several different foods, such as evergreen huckleberries (Vaccinium ovatum), mundus (Garcinia dulcis), persimmons (Diospyros), nopals (Opuntia cochenillifera), and common buckwheats (Fagopyrum esculentum). This could make 4-fumarylacetoacetic acid a potential biomarker for the consumption of these foods. 4-Fumarylacetoacetic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 4-Fumarylacetoacetic acid.
Structure
Data?1582752188
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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.65 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available31661259
DarkChem[M-H]-PredictedNot Available31661259
AllCCS[M+H]+PredictedNot Available142.57632859911
AllCCS[M-H]-PredictedNot Available138.72232859911

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9300000000-7b2ae90eb353073cb6522017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05bu-7092000000-254fb0c9b4683fd48ef12017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsi-1920000000-f36f976fb4a0271e936b2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-6900000000-692cbcc9f99aac913e422016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rj-9200000000-8e21be4180492b988f542016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-1900000000-ea634f49698a94be63112016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5900000000-4d5261faac7c9dc29c362016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-17b0a81ad882f626ac2a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-4900000000-80aa92977bd40f96e7402021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-9100000000-7d688d7f7d7a804690a32021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c0d2eba6487ff950c63d2021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 IDC00007599
Chemspider ID4444081
KEGG Compound IDC01061
BioCyc ID4-FUMARYL-ACETOACETATE
BiGG ID1485275
Wikipedia LinkFumarylacetoacetic_acid
METLIN ID6123
PubChem Compound5280398
PDB IDNot Available
ChEBI ID30907
Food Biomarker OntologyNot Available
VMH ID4FUMACAC
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in fumarylacetoacetase activity
Specific function:
Not Available
Gene Name:
FAH
Uniprot ID:
P16930
Molecular weight:
46373.97
Reactions
4-Fumarylacetoacetic acid + Water → Acetoacetic acid + Fumaric aciddetails
Acetoacetic acid + Fumaric acid → 4-Fumarylacetoacetic acid + Waterdetails
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