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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:01 UTC

HMDB ID

HMDB0000635

Secondary Accession Numbers

HMDB00635

Metabolite Identification

Common Name

Succinylacetone

Description

Succinylacetone, also known as 4,6-dioxoheptanoic acid or SUAC, belongs to the class of compounds known as medium-chain keto acids and derivatives. These are keto acids with 6 to 12 carbon atoms. Succinylacetone is soluble (in water) and a weakly acidic compound (based on its pKa). Succinylacetone has been detected in amniotic fluid, blood, and urine. Within the cell, succinylacetone is primarily located in the cytoplasm (predicted from logP). Succinylacetone can be created by the oxidation of glycine, and is a precursor of methylglyoxal (Wikipedia ). Succinylacetone is an abnormal tyrosine metabolite that arises from defects in the enzyme called fumarylacetoacetase (PMID: 16448836 ). Fumarylacetoacetase normally catalyzes the hydrolysis of 4-fumarylacetoacetate into fumarate and acetoacetate. If present in sufficiently high levels, succinylacetone can act as an acidogen, an oncometabolite, and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. An oncometabolite is an endogenous metabolite that causes cancer. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of succinylacetone are associated with tyrosinemia type I. Type I tyrosinemia is an inherited metabolism disorder due to a shortage of the enzyme fumarylacetoacetate hydrolase that is needed to break down tyrosine. Patients usually develop features such as hepatic necrosis, renal tubular injury, and hypertrophic cardiomyopathy. Neurologic and dermatologic manifestations are also possible. The urine has an odour of cabbage or rancid butter. Succinylacetone is a keto-acid, which is a subclass of organic acids. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated tyrosinemia. Many affected children with organic acidemias experience intellectual disability or delayed development. Succinylacetone appears to function as an oncometabolite (similar in function to succinate, another oncometabolite) as patients with high levels of this compound often develop hepatocellular carcinoma (PMID: 20003495 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4,6-Dioxoheptanoate	HMDB
4,6-Dioxoheptanoic acid	HMDB
Succinylacetone	ChEBI

Chemical Formula

C₇H₁₀O₄

Average Molecular Weight

158.1519

Monoisotopic Molecular Weight

158.057908808

IUPAC Name

4,6-dioxoheptanoic acid

Traditional Name

succinylacetone

CAS Registry Number

51568-18-4

SMILES

CC(=O)CC(=O)CCC(O)=O

InChI Identifier

InChI=1S/C7H10O4/c1-5(8)4-6(9)2-3-7(10)11/h2-4H2,1H3,(H,10,11)

InChI Key

WYEPBHZLDUPIOD-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
1,3-diketone
1,3-dicarbonyl compound
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Tyrosinemia I (HMDB: HMDB0000635)
Tyrosinemia (HMDB: HMDB0000635)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16414314)
Amniotic Fluid (PMID: 16414314)

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Cellular substructure

Cytoplasm (HMDB: HMDB0000635)
Extracellular (HMDB: HMDB0000635)

Source

Endogenous

Endogenous (HMDB: HMDB0000635)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Tyrosinemia Type I (HMDB: HMDB0000635)

Role

Indirect biological role

Metabotoxin

Metabotoxin (HMDB: HMDB0000635)

Biological role

Oncometabolite (HMDB: HMDB0000635)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	66 - 67 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	257900 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	131.436	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001768

Predicted Molecular Properties

Property	Value	Source
Water Solubility	24.1 g/L	ALOGPS
logP	-0.18	ALOGPS
logP	0.15	ChemAxon
logS	-0.82	ALOGPS
pKa (Strongest Acidic)	4.15	ChemAxon
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	36.98 m³·mol⁻¹	ChemAxon
Polarizability	15.07 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	135.599	32859911
AllCCS	[M-H]-	132.648	32859911
DeepCCS	[M+H]+	130.566	30932474
DeepCCS	[M-H]-	126.787	30932474
DeepCCS	[M-2H]-	164.011	30932474
DeepCCS	[M+Na]+	139.395	30932474
AllCCS	[M+H]+	135.6	32859911
AllCCS	[M+H-H2O]+	131.6	32859911
AllCCS	[M+NH4]+	139.3	32859911
AllCCS	[M+Na]+	140.4	32859911
AllCCS	[M-H]-	132.6	32859911
AllCCS	[M+Na-2H]-	134.5	32859911
AllCCS	[M+HCOO]-	136.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Succinylacetone	CC(=O)CC(=O)CCC(O)=O	2718.4	Standard polar	33892256
Succinylacetone	CC(=O)CC(=O)CCC(O)=O	1157.3	Standard non polar	33892256
Succinylacetone	CC(=O)CC(=O)CCC(O)=O	1353.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Succinylacetone,1TMS,isomer #1	CC(=O)CC(=O)CCC(=O)O[Si](C)(C)C	1418.8	Semi standard non polar	33892256
Succinylacetone,1TMS,isomer #2	CC(=CC(=O)CCC(=O)O)O[Si](C)(C)C	1536.7	Semi standard non polar	33892256
Succinylacetone,1TMS,isomer #3	CC(=O)CC(=CCC(=O)O)O[Si](C)(C)C	1481.0	Semi standard non polar	33892256
Succinylacetone,1TMS,isomer #4	CC(=O)C=C(CCC(=O)O)O[Si](C)(C)C	1560.5	Semi standard non polar	33892256
Succinylacetone,1TMS,isomer #5	C=C(CC(=O)CCC(=O)O)O[Si](C)(C)C	1482.7	Semi standard non polar	33892256
Succinylacetone,2TMS,isomer #1	CC(=CC(=O)CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1633.4	Semi standard non polar	33892256
Succinylacetone,2TMS,isomer #1	CC(=CC(=O)CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1562.1	Standard non polar	33892256
Succinylacetone,2TMS,isomer #1	CC(=CC(=O)CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1736.2	Standard polar	33892256
Succinylacetone,2TMS,isomer #2	CC(=O)CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1583.2	Semi standard non polar	33892256
Succinylacetone,2TMS,isomer #2	CC(=O)CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1545.9	Standard non polar	33892256
Succinylacetone,2TMS,isomer #2	CC(=O)CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1709.6	Standard polar	33892256
Succinylacetone,2TMS,isomer #3	CC(=O)C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1626.5	Semi standard non polar	33892256
Succinylacetone,2TMS,isomer #3	CC(=O)C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1562.3	Standard non polar	33892256
Succinylacetone,2TMS,isomer #3	CC(=O)C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1749.4	Standard polar	33892256
Succinylacetone,2TMS,isomer #4	C=C(CC(=O)CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1565.8	Semi standard non polar	33892256
Succinylacetone,2TMS,isomer #4	C=C(CC(=O)CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1576.6	Standard non polar	33892256
Succinylacetone,2TMS,isomer #4	C=C(CC(=O)CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1775.8	Standard polar	33892256
Succinylacetone,2TMS,isomer #5	CC(=CC(=CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	1728.1	Semi standard non polar	33892256
Succinylacetone,2TMS,isomer #5	CC(=CC(=CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	1687.2	Standard non polar	33892256
Succinylacetone,2TMS,isomer #5	CC(=CC(=CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	1970.3	Standard polar	33892256
Succinylacetone,2TMS,isomer #6	C=C(CC(=CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	1631.6	Semi standard non polar	33892256
Succinylacetone,2TMS,isomer #6	C=C(CC(=CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	1659.1	Standard non polar	33892256
Succinylacetone,2TMS,isomer #6	C=C(CC(=CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	2018.0	Standard polar	33892256
Succinylacetone,2TMS,isomer #7	C=C(C=C(CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	1666.9	Semi standard non polar	33892256
Succinylacetone,2TMS,isomer #7	C=C(C=C(CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	1616.5	Standard non polar	33892256
Succinylacetone,2TMS,isomer #7	C=C(C=C(CCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C	1915.3	Standard polar	33892256
Succinylacetone,3TMS,isomer #1	CC(=CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1747.3	Semi standard non polar	33892256
Succinylacetone,3TMS,isomer #1	CC(=CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1688.6	Standard non polar	33892256
Succinylacetone,3TMS,isomer #1	CC(=CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1661.2	Standard polar	33892256
Succinylacetone,3TMS,isomer #2	C=C(CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1659.6	Semi standard non polar	33892256
Succinylacetone,3TMS,isomer #2	C=C(CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1664.6	Standard non polar	33892256
Succinylacetone,3TMS,isomer #2	C=C(CC(=CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1649.7	Standard polar	33892256
Succinylacetone,3TMS,isomer #3	C=C(C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1677.7	Semi standard non polar	33892256
Succinylacetone,3TMS,isomer #3	C=C(C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1661.3	Standard non polar	33892256
Succinylacetone,3TMS,isomer #3	C=C(C=C(CCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C	1645.4	Standard polar	33892256
Succinylacetone,1TBDMS,isomer #1	CC(=O)CC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C	1657.6	Semi standard non polar	33892256
Succinylacetone,1TBDMS,isomer #2	CC(=CC(=O)CCC(=O)O)O[Si](C)(C)C(C)(C)C	1769.2	Semi standard non polar	33892256
Succinylacetone,1TBDMS,isomer #3	CC(=O)CC(=CCC(=O)O)O[Si](C)(C)C(C)(C)C	1739.1	Semi standard non polar	33892256
Succinylacetone,1TBDMS,isomer #4	CC(=O)C=C(CCC(=O)O)O[Si](C)(C)C(C)(C)C	1805.4	Semi standard non polar	33892256
Succinylacetone,1TBDMS,isomer #5	C=C(CC(=O)CCC(=O)O)O[Si](C)(C)C(C)(C)C	1718.3	Semi standard non polar	33892256
Succinylacetone,2TBDMS,isomer #1	CC(=CC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2094.3	Semi standard non polar	33892256
Succinylacetone,2TBDMS,isomer #1	CC(=CC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2018.4	Standard non polar	33892256
Succinylacetone,2TBDMS,isomer #1	CC(=CC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2003.8	Standard polar	33892256
Succinylacetone,2TBDMS,isomer #2	CC(=O)CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2030.4	Semi standard non polar	33892256
Succinylacetone,2TBDMS,isomer #2	CC(=O)CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1980.6	Standard non polar	33892256
Succinylacetone,2TBDMS,isomer #2	CC(=O)CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1978.4	Standard polar	33892256
Succinylacetone,2TBDMS,isomer #3	CC(=O)C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2067.9	Semi standard non polar	33892256
Succinylacetone,2TBDMS,isomer #3	CC(=O)C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2002.2	Standard non polar	33892256
Succinylacetone,2TBDMS,isomer #3	CC(=O)C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2011.4	Standard polar	33892256
Succinylacetone,2TBDMS,isomer #4	C=C(CC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2003.0	Semi standard non polar	33892256
Succinylacetone,2TBDMS,isomer #4	C=C(CC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1994.3	Standard non polar	33892256
Succinylacetone,2TBDMS,isomer #4	C=C(CC(=O)CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2036.8	Standard polar	33892256
Succinylacetone,2TBDMS,isomer #5	CC(=CC(=CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2184.4	Semi standard non polar	33892256
Succinylacetone,2TBDMS,isomer #5	CC(=CC(=CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2072.4	Standard non polar	33892256
Succinylacetone,2TBDMS,isomer #5	CC(=CC(=CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2154.9	Standard polar	33892256
Succinylacetone,2TBDMS,isomer #6	C=C(CC(=CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2072.7	Semi standard non polar	33892256
Succinylacetone,2TBDMS,isomer #6	C=C(CC(=CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2029.7	Standard non polar	33892256
Succinylacetone,2TBDMS,isomer #6	C=C(CC(=CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2192.1	Standard polar	33892256
Succinylacetone,2TBDMS,isomer #7	C=C(C=C(CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2106.5	Semi standard non polar	33892256
Succinylacetone,2TBDMS,isomer #7	C=C(C=C(CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1980.9	Standard non polar	33892256
Succinylacetone,2TBDMS,isomer #7	C=C(C=C(CCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2123.8	Standard polar	33892256
Succinylacetone,3TBDMS,isomer #1	CC(=CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2399.5	Semi standard non polar	33892256
Succinylacetone,3TBDMS,isomer #1	CC(=CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2299.2	Standard non polar	33892256
Succinylacetone,3TBDMS,isomer #1	CC(=CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2055.6	Standard polar	33892256
Succinylacetone,3TBDMS,isomer #2	C=C(CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2321.2	Semi standard non polar	33892256
Succinylacetone,3TBDMS,isomer #2	C=C(CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2238.5	Standard non polar	33892256
Succinylacetone,3TBDMS,isomer #2	C=C(CC(=CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2077.8	Standard polar	33892256
Succinylacetone,3TBDMS,isomer #3	C=C(C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2332.6	Semi standard non polar	33892256
Succinylacetone,3TBDMS,isomer #3	C=C(C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2237.3	Standard non polar	33892256
Succinylacetone,3TBDMS,isomer #3	C=C(C=C(CCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2082.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9200000000-418fe15f4a3ff86cd732	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9510000000-9b8725af310299084be0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Succinylacetone GC-MS (TBDMS_1_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000f-9100000000-a3b92f310030718acb91	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Succinylacetone Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a4i-0900000000-bc1ed64644f1d5262a67	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Succinylacetone Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4l-4900000000-4a799061d93a46eb98ab	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Succinylacetone Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0a4i-1900000000-bb8ea63020dfb2d73fd6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Succinylacetone 20V, Positive-QTOF	splash10-0fdy-9000000000-d000e19711c34e043ab9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Succinylacetone 20V, Positive-QTOF	splash10-0002-9000000000-60a15fc8627ad96e8532	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Succinylacetone 10V, Positive-QTOF	splash10-0002-9400000000-d9f2cde762a2868297c3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Succinylacetone 40V, Positive-QTOF	splash10-0a59-9000000000-0c4c76b64acd6d49029a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Succinylacetone 40V, Positive-QTOF	splash10-0006-9000000000-03c08ce11d1bfc6939ac	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Succinylacetone 10V, Positive-QTOF	splash10-0002-9100000000-940ff687b04afbb69085	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 10V, Positive-QTOF	splash10-006x-1900000000-78eabe7ae2f320bd578f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 20V, Positive-QTOF	splash10-0kml-7900000000-db14b02751e17fac3323	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 40V, Positive-QTOF	splash10-0a4i-9100000000-b6e51a674fbdfbbe701a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 10V, Negative-QTOF	splash10-0a4i-1900000000-cfd9bc7542d69961cfde	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 20V, Negative-QTOF	splash10-0a4r-5900000000-3abd8a41f7a1bab5e9a2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 40V, Negative-QTOF	splash10-0a4i-9200000000-63209abdb7044cb484b2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 10V, Negative-QTOF	splash10-014i-9600000000-e6fe2f0606f1545e63f8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 20V, Negative-QTOF	splash10-0601-9300000000-f4da7f3a1baacd6285c2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 40V, Negative-QTOF	splash10-0a4i-9000000000-9a962f60cab056b14ceb	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 10V, Positive-QTOF	splash10-0006-9500000000-8ab84079b41abee33201	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 20V, Positive-QTOF	splash10-0007-9000000000-4c7d97bda3ec2644c3b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Succinylacetone 40V, Positive-QTOF	splash10-052f-9000000000-1b9dad08fc2bac65faee	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, 5%_DMSO, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Amniotic Fluid
Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Amniotic Fluid	Detected and Quantified	0.003 (0.00-0.013) uM	Adult (>18 years old)	Both	Normal	16414314	details
Blood	Detected and Quantified	0.15 (0.00-0.30) uM	Adult (>18 years old)	Both	Normal	17133337	details
Blood	Detected and Quantified	0.013 (0.003-0.021) uM	Adult (>18 years old)	Both	Normal	16414314	details
Urine	Detected and Quantified	0-10 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	31506554	details
Urine	Detected and Quantified	2.8 (0.6-4.7) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	8.329 +/- 5.467 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	327.300 +/- 125.8(190-543) uM	Children (1-13 years old)	Both	Tyrosinemia I	22455637	details
Blood	Detected and Quantified	3.3 (0.9-5.7) uM	Adult (>18 years old)	Both	Hepatorenal tyrosinemia type I	17133337	details
Blood	Detected and Quantified	0.033 (0.021-0.055) uM	Adult (>18 years old)	Both	Tyrosinemia	16414314	details
Urine	Detected and Quantified	9.683 +/- 7.284 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Tyrosinemia
Cyr D, Giguere R, Villain G, Lemieux B, Drouin R: A GC/MS validated method for the nanomolar range determination of succinylacetone in amniotic fluid and plasma: an analytical tool for tyrosinemia type I. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Feb 17;832(1):24-9. Epub 2006 Jan 18. [PubMed:16414314 ]
Tyrosinemia I
Han LS, Ye J, Qiu WJ, Zhang HW, Wang Y, Ji WJ, Gao XL, Li XY, Jin J, Gu XF: [Application of succinylacetone levels measurement in the blood and urine in the diagnosis of tyrosinemia type 1]. Zhonghua Er Ke Za Zhi. 2012 Feb;50(2):126-30. [PubMed:22455637 ] G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

276700 (Tyrosinemia)
276700 (Tyrosinemia I)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022156

KNApSAcK ID

C00052413

Chemspider ID

5121

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Succinylacetone

METLIN ID

5608

PubChem Compound

5312

PDB ID

Not Available

ChEBI ID

87897

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1196051

References

Synthesis Reference

Levenson, Corey H. Process for the preparation of succinylacetone. PCT Int. Appl. (1991), 9 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Fernandez-Canon JM, Baetscher MW, Finegold M, Burlingame T, Gibson KM, Grompe M: Maleylacetoacetate isomerase (MAAI/GSTZ)-deficient mice reveal a glutathione-dependent nonenzymatic bypass in tyrosine catabolism. Mol Cell Biol. 2002 Jul;22(13):4943-51. [PubMed:12052898 ]
Laberge C, Lescault A, Grenier A, Morrisette J, Gagne R, Gadbois P, Halket J: Oral loading of homogentisic acid in controls and in obligate heterozygotes for hereditary tyrosinemia type I. Am J Hum Genet. 1990 Aug;47(2):329-37. [PubMed:2378359 ]
Poudrier J, Lettre F, St-Louis M, Tanguay RM: Genotyping of a case of tyrosinaemia type I with normal level of succinylacetone in amniotic fluid. Prenat Diagn. 1999 Jan;19(1):61-3. [PubMed:10073910 ]
Jakobs C, Dorland L, Wikkerink B, Kok RM, de Jong AP, Wadman SK: Stable isotope dilution analysis of succinylacetone using electron capture negative ion mass fragmentography: an accurate approach to the pre- and neonatal diagnosis of hereditary tyrosinemia type I. Clin Chim Acta. 1988 Feb 15;171(2-3):223-31. [PubMed:3286060 ]
Kimura A, Endo F, Kagimoto S, Inoue T, Suzuki M, Kurosawa T, Tohma M, Fujisawa T, Kato H: Tyrosinemia type I-like disease: a possible manifestation of 3-oxo-delta 4-steroid 5 beta-reductase deficiency. Acta Paediatr Jpn. 1998 Jun;40(3):211-7. [PubMed:9695292 ]
Magera MJ, Gunawardena ND, Hahn SH, Tortorelli S, Mitchell GA, Goodman SI, Rinaldo P, Matern D: Quantitative determination of succinylacetone in dried blood spots for newborn screening of tyrosinemia type I. Mol Genet Metab. 2006 May;88(1):16-21. Epub 2006 Jan 31. [PubMed:16448836 ]
Endo F, Katoh H, Yamamoto S, Matsuda I: A murine model for type III tyrosinemia: lack of immunologically detectable 4-hydroxyphenylpyruvic acid dioxygenase enzyme protein in a novel mouse strain with hypertyrosinemia. Am J Hum Genet. 1991 Apr;48(4):704-9. [PubMed:2014797 ]
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. [PubMed:20003495 ]

Showing metabocard for Succinylacetone (HMDB0000635)

MOL for HMDB0000635 (Succinylacetone)

3D MOL for HMDB0000635 (Succinylacetone)

3D SDF for HMDB0000635 (Succinylacetone)

3D-SDF for HMDB0000635 (Succinylacetone)

PDB for HMDB0000635 (Succinylacetone)

3D PDB for HMDB0000635 (Succinylacetone)

SMILES for HMDB0000635 (Succinylacetone)

INCHI for HMDB0000635 (Succinylacetone)

Structure for HMDB0000635 (Succinylacetone)

3D Structure for HMDB0000635 (Succinylacetone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra