Succinyl acetoacetate (CHEM003953)

Record Information
Version1.0
Creation Date2014-10-15 22:09:23 UTC
Update Date2026-04-06 12:35:33 UTC
Accession NumberCHEM003953
Identification
Common NameSuccinyl acetoacetate
ClassSmall Molecule
Description
Succinyl acetoacetate is a toxic metabolite identified in people with hereditary tyrosinemia.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Metabolite
  • Natural Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,5-Dioxosuberic acidChEBI
Succinyl-acetoacetateChEBI
SuccinylacetoacetateChEBI
3,5-DioxosuberateGenerator
Succinyl-acetoacetic acidGenerator
Succinylacetoacetic acidGenerator
Succinyl acetoacetic acidGenerator
3,5-Dioxooctanedioic acidHMDB
Chemical FormulaC8H10O6
Average Molecular Mass202.161 g/mol
Monoisotopic Mass202.048 g/mol
CAS Registry Number65115-74-4
IUPAC Name3,5-dioxooctanedioic acid
Traditional Name3,5-dioxooctanedioic acid
SMILES[H]OC(=O)C([H])([H])C(=O)C([H])([H])C(=O)C([H])([H])C([H])([H])C(=O)O[H]
InChI IdentifierInChI=1S/C8H10O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-4H2,(H,11,12)(H,13,14)
InChI KeyOMFWHSRZHVVVAL-UHFFFAOYSA-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
  • Gamma-keto acid
  • Beta-keto acid
  • 1,3-diketone
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoskeleton
  • Cytosol
  • Extracellular
  • Membrane Fraction
  • Mitochondrial Matrix
  • Mitochondrion
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Insulin secretionNot Availablemap04911
Oxidative phosphorylationNot Availablemap00190
Metabolic PathwaysNot AvailableNot Available
Butanoate metabolismNot Availablemap00650
Starch and Sucrose MetabolismSMP00058 map00500
Pyruvate MetabolismSMP00060 map00620
Methane MetabolismNot AvailableNot Available
Fatty acid MetabolismSMP00051 map00071
Fatty Acid BiosynthesisSMP00456 map00061
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.66 g/LALOGPS
logP-0.56ALOGPS
logP0.045ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area108.74 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity43.33 m³·mol⁻¹ChemAxon
Polarizability17.72 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsChronically high levels of succinylacetoacetate are associated with Tyrosinemia Type I.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0240258
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID111425
ChEBI ID87999
PubChem Compound ID125181
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17513424
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20003495
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=2611997
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=7171740
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=7246125