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Showing Compound 4-Fumarylacetoacetic acid (FDB022522)

Record Information
Version1.0
Creation date2011-09-21 00:15:16 UTC
Update date2020-09-17 15:38:53 UTC
Primary IDFDB022522
Secondary Accession Numbers
  • FDB030495
  • FDB022817
Chemical Information
FooDB 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. 4-Fumarylacetoacetic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 4-fumarylacetoacetic acid participates in a number of enzymatic reactions. In particular, 4-fumarylacetoacetic acid can be biosynthesized from maleylacetoacetic acid through its interaction with the enzyme maleylacetoacetate isomerase. In addition, 4-fumarylacetoacetic acid can be converted into acetoacetic acid and fumaric acid; which is mediated by the enzyme fumarylacetoacetase. In humans, 4-fumarylacetoacetic acid is involved in the metabolic disorder called tyrosinemia type 3 (tyro3). Outside of the human body, 4-Fumarylacetoacetic acid has been detected, but not quantified in, several different foods, such as walnuts, lupines, narrowleaf cattails, wild carrots, and japanese walnuts. This could make 4-fumarylacetoacetic acid a potential biomarker for the consumption of these foods.
CAS Number28613-33-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
FumarylacetoacetoneChEBI
FumarylacetoacetateKegg
Fumarylacetoacetic acidGenerator
4-FumarylacetoacetateGenerator
4-Fumaryl-acetoacetateHMDB
(2E)-4,6-Dioxo-2-octenedioic acidHMDB
4-Fumarylacetoacetic acidHMDB
(E)-4,6-dioxo-2-Octenedioatehmdb
(E)-4,6-dioxo-2-Octenedioic acidhmdb
4-fumaryl-acetoacetatehmdb
4-fumarylacetoacetatehmdb
Predicted 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
Chemical FormulaC8H8O6
IUPAC name(2E)-4,6-dioxooct-2-enedioic acid
InChI IdentifierInChI=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
Isomeric SMILESOC(=O)CC(=O)CC(=O)\C=C\C(O)=O
Average Molecular Weight200.1455
Monoisotopic Molecular Weight200.032087988
Classification
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:

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Fumarylacetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-9300000000-7b2ae90eb353073cb652Spectrum
Predicted GC-MS4-Fumarylacetoacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05bu-7092000000-254fb0c9b4683fd48ef1Spectrum
Predicted GC-MS4-Fumarylacetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Fumarylacetoacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsi-1920000000-f36f976fb4a0271e936b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-6900000000-692cbcc9f99aac913e422016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rj-9200000000-8e21be4180492b988f542016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-1900000000-ea634f49698a94be63112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5900000000-4d5261faac7c9dc29c362016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-17b0a81ad882f626ac2a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-3900000000-0353447aa417ab1cef292021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9600000000-fabbd099eded8f7879a92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-e4bd7674e02d56b3573f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-4900000000-80aa92977bd40f96e7402021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-9100000000-7d688d7f7d7a804690a32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c0d2eba6487ff950c63d2021-09-24View Spectrum
NMRNot Available
ChemSpider ID4444081
ChEMBL IDNot Available
KEGG Compound IDC01061
Pubchem Compound ID5280398
Pubchem Substance IDNot Available
ChEBI ID30907
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01268
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1485275
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDFumarylacetoacetate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Maleylacetoacetate isomeraseGSTZ1O43708
Pathways
NameSMPDB LinkKEGG Link
Phenylalanine and Tyrosine MetabolismSMP00008 map00360
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference