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Succinylacetone

By rofalproject
Common Name

Succinylacetone Description

Succinylacetone is a tyrosine metabolite (PMID 16448836 ). It is a specific marker for 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. (Wikipedia). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 4,6-DioxoheptanoateHMDB 4,6-Dioxoheptanoic acidHMDB

Chemical Formlia

C7H10O4 Average Molecliar Weight

158.1519 Monoisotopic Molecliar 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

This compound belongs to the class of chemical entities known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Keto acids and derivatives Direct Parent

Medium-chain keto acids and derivatives Alternative Parents

  • Gamma-keto acids and derivatives
  • Beta-diketones
  • Ketones
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organic oxides
  • Hydrocarbon derivatives

    • 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

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

    Not Available Ontology Status

    Detected and Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

  • Cytoplasm (predicted from logP)

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point66 – 67 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility24.1 mg/mLALOGPS logP-0.18ALOGPS logP0.15ChemAxon logS-0.82ALOGPS pKa (Strongest Acidic)4.15ChemAxon pKa (Strongest Basic)-7.2ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area71.44 Å2ChemAxon Rotatable Bond Count5ChemAxon Refractivity36.98 m3·mol-1ChemAxon Polarizability15.07 Å3ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0900000000-bc1ed64644f1d5262a67View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-4900000000-4a799061d93a46eb98abView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-1900000000-bb8ea63020dfb2d73fd6View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-006x-1900000000-78eabe7ae2f320bd578fView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0kml-7900000000-db14b02751e17fac3323View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0a4i-9100000000-b6e51a674fbdfbbe701aView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-0a4i-1900000000-cfd9bc7542d69961cfdeView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0a4r-5900000000-3abd8a41f7a1bab5e9a2View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0a4i-9200000000-63209abdb7044cb484b2View in MoNA MS

    Mass Spectrum (Electron Ionization)splash10-000f-9100000000-a3b92f310030718acb91View in MoNA 1D NMR

    1H NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm (predicted from logP)

    • Biofluid Locations

  • Amniotic Fluid
  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details Amniotic FluidDetected and Quantified0.003 (0.00-0.013) uMAdlit (>18 years old)BothNormal

  • 16414314

    • details BloodDetected and Quantified0.15 (0.00-0.30) uMAdlit (>18 years old)BothNormal

  • 17133337

    • details BloodDetected and Quantified0.013 (0.003-0.021) uMAdlit (>18 years old)BothNormal

  • 16414314

    • details UrineDetected and Quantified2.8 (0.6-4.7) umol/mmol creatinineAdlit (>18 years old)Both

    Normal

  • 24023812

    • details UrineDetected and Quantified8.329 +/- 5.467 umol/mmol creatinineChildren (1 – 13 years old)Not Specified

    Normal

  • Mordechai, Hien, …

    • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified3.3 (0.9-5.7) uMAdlit (>18 years old)BothHepatorenal tyrosinemia type I

  • 17133337

    • details BloodDetected and Quantified0.033 (0.021-0.055) uMAdlit (>18 years old)Both

    Tyrosinemia

  • 16414314

    • details UrineDetected and Quantified1.0 (0.0-2.0) umol/mmol creatinineAdlit (>18 years old)BothTyrosinemia I

  • MetaGene

    • details UrineDetected and Quantified360.00 (20.00-700.00) umol/mmol creatinineChildren (1-13 years old)BothTyrosinemia I

  • MetaGene

    • details UrineDetected and Quantified9.683 +/- 7.284 umol/mmol creatinineChildren (1 – 13 years old)Not Specified

    Eosinophilic esophagitis

  • Mordechai, Hien, …

    • details

    Associated Disorders and Diseases Disease References

    Tyrosinemia

    1. 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

    1. MetaGene [Link]

    Associated OMIM IDs

  • 276700 (Tyrosinemia)
  • 276700 (Tyrosinemia I)

    • External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB022156 KNApSAcK ID

    Not Available Chemspider ID

    5121 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB00635 Metagene Link

    HMDB00635 METLIN ID

    5608 PubChem Compound

    5312 PDB ID

    SHU ChEBI ID

    Not Available

    Product: Lycorine (hydrochloride)

    References Synthesis Reference Levenson, Corey H. Process for the preparation of succinylacetone. PCT Int. Appl. (1991), 9 pp. Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. 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 ]
    2. 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 ]
    3. 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 ]
    4. 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 ]
    5. 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 ]
    6. 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 ]
    7. 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 ]

    PMID: 9589348

    By rofalproject

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