ContaminantDB: Succinyl acetoacetate

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Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-10-15 22:09:23 UTC

Update Date

2016-11-09 01:09:15 UTC

Accession Number

CHEM003953

Identification

Common Name

Succinyl acetoacetate

Class

Small 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,5-Dioxosuberic acid	ChEBI
Succinyl-acetoacetate	ChEBI
Succinylacetoacetate	ChEBI
3,5-Dioxosuberate	Generator
Succinyl-acetoacetic acid	Generator
Succinylacetoacetic acid	Generator
Succinyl acetoacetic acid	Generator
3,5-Dioxooctanedioic acid	HMDB

Chemical Formula

C₈H₁₀O₆

Average Molecular Mass

202.161 g/mol

Monoisotopic Mass

202.048 g/mol

CAS Registry Number

65115-74-4

IUPAC Name

3,5-dioxooctanedioic acid

Traditional Name

3,5-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 Identifier

InChI=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 Key

OMFWHSRZHVVVAL-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoskeleton
Cytosol
Extracellular
Membrane Fraction
Mitochondrial Matrix
Mitochondrion

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Insulin secretion	Not Available	map04911
Oxidative phosphorylation	Not Available	map00190
Metabolic Pathways	Not Available	Not Available
Butanoate metabolism	Not Available	map00650
Starch and Sucrose Metabolism	SMP00058	map00500
Pyruvate Metabolism	SMP00060	map00620
Methane Metabolism	Not Available	Not Available
Fatty acid Metabolism	SMP00051	map00071
Fatty Acid Biosynthesis	SMP00456	map00061

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.66 g/L	ALOGPS
logP	-0.56	ALOGPS
logP	0.045	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	43.33 m³·mol⁻¹	ChemAxon
Polarizability	17.72 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-1920000000-22c7089e732e52f51956	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-5900000000-3ca1ab6d1f60b5276b83	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9200000000-27c4746155a2bf563b4d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-2950000000-b298b52855b7e52a39d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-5900000000-7f946ff237e2d2e0574d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9500000000-8273967ad8e55cae9074	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfs-6910000000-51d444e0d2a7348705ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06r6-9500000000-0f1867f6d485728fc23e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abc-9000000000-7cb03fab668c620b77c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-4900000000-fdbdf265adb371131e3b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000e-9300000000-8dd9a3181010bae1e489	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0536-9000000000-a42cd704adb3322429a8	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Chronically high levels of succinylacetoacetate are associated with Tyrosinemia Type I.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0240258

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

111425

ChEBI ID

87999

PubChem Compound ID

125181

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not 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

Succinyl acetoacetate (CHEM003953)

Structure for CHEM003953: Succinyl acetoacetate