Showing Compound Card for 4-Fumarylacetoacetic acid (CDB004903)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (2) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-04-17 18:48:48 UTC
Updated at2020-11-18 16:38:58 UTC
CannabisDB IDCDB004903
Secondary Accession NumbersNot Available
Cannabis Compound 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. 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. 4-Fumarylacetoacetic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.
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 Weight200.15
Monoisotopic Molecular Weight200.0321
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:

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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
FumarylacetoacetaseFAH15q25.1P16930 details
Maleylacetoacetate isomeraseGSTZ114q24.3O43708 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
FumarylacetoacetaseFAH15q25.1P16930 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001268
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Enzymes

Enzyme Details
1. Fumarylacetoacetase
General function:
Involved in fumarylacetoacetase activity
Specific function:
Not Available
Gene Name:
FAH
Uniprot ID:
P16930
Molecular weight:
46373.97
Enzyme Details
2. 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