Tmic
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Database of hazardous chemicals.
Record Information
Version1.0
Creation Date2014-10-15 22:09:23 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003953
Identification
Common NameSuccinyl acetoacetate
ClassSmall Molecule
DescriptionSuccinyl acetoacetate is a toxic metabolite identified in people with hereditary tyrosinemia.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Animal Toxin
  • Metabolite
  • Natural Compound
Chemical Structure
Thumb
Synonyms
ValueSource
3,5-Dioxosuberic acidChEBI
Succinyl-acetoacetateChEBI
3,5-DioxosuberateGenerator
Succinyl-acetoacetic acidGenerator
Succinylacetoacetic acidGenerator
Succinyl acetoacetic acidHMDB
3,5-Dioxooctanedioic acidHMDB
SuccinylacetoacetateChEBI
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-1920000000-22c7089e732e52f51956View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5900000000-3ca1ab6d1f60b5276b83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9200000000-27c4746155a2bf563b4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-2950000000-b298b52855b7e52a39d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5900000000-7f946ff237e2d2e0574dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-8273967ad8e55cae9074View in MoNA
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
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 IDNot Available
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
6. Lindblad B, Steen G: Identification of 4,6-dioxoheptanoic acid (succinylacetone), 3,5-dioxooctanedioic acid (succinylacetoacetate) and 4-Oxo-6-hydroxyheptanoic acid in the urine from patients with hereditary tyrosinemia. Biomed Mass Spectrom. 1982 Oct;9(10):419-24.
7. Cassiman D, Zeevaert R, Holme E, Kvittingen EA, Jaeken J: A novel mutation causing mild, atypical fumarylacetoacetase deficiency (Tyrosinemia type I): a case report. Orphanet J Rare Dis. 2009 Dec 15;4:28. doi: 10.1186/1750-1172-4-28.