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Succinic semialdehyde

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(Redirected from 4-Oxobutyric acid)
Succinic semialdehyde
Names
Preferred IUPAC name 4-Oxobutanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.155.728 Edit this at Wikidata
KEGG
MeSH Succinic+semialdehyde
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)Key: UIUJIQZEACWQSV-UHFFFAOYSA-N
  • InChI=1/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)Key: UIUJIQZEACWQSV-UHFFFAOYAS
SMILES
  • O=CCCC(=O)O
Properties
Chemical formula C4H6O3
Molar mass 102.089 g/mol
Appearance oil
Boiling point 135 °C (275 °F; 408 K) at 14 mmHg
Solubility in water soluble in water, ethanol, benzene, diethyl ether
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Succinic semialdehyde (SSA) is a GABA and GHB metabolite. It is formed from GABA by the action of GABA transaminase (4-aminobutyrate aminotransferase) and further oxidised to become succinic acid, which enters TCA cycle. SSA is oxidized into succinic acid by the enzyme succinic semialdehyde dehydrogenase, which uses NAD as a cofactor.   When the oxidation of succinic semialdehyde to succinic acid is impaired, accumulation of succinic semialdehyde takes place which leads to succinic semialdehyde dehydrogenase deficiency.

In addition to the pathway involving GABA transaminase, gamma-hydroxybutyric acid (GHB) can also be metabolized to SSA via GHB dehydrogenase or by GHB transhydrogenase (D-2-hydroxyglutarate transhydrogenase).

See also

References

  1. Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, Florida: CRC Press, pp. 3–446, ISBN 0-8493-0594-2
  2. Peng, Qi; Yang, Min; Wang, Wei; Han, Lili; Wang, Guannan; Wang, Pengyue; Zhang, Jie; Song, Fuping (2014-12-20). "Activation of gab cluster transcription in Bacillus thuringiensis by γ-aminobutyric acid or succinic semialdehyde is mediated by the Sigma 54-dependent transcriptional activator GabR". BMC Microbiology. 14 (1): 306. doi:10.1186/s12866-014-0306-3. ISSN 1471-2180. PMC 4279683. PMID 25527261.
  3. ^ Struys, E. A.; Jansen, E. E. W.; Gibson, K. M.; Jakobs, C. (December 2005). "Determination of the GABA analogue succinic semialdehyde in urine and cerebrospinal fluid by dinitrophenylhydrazine derivatization and liquid chromatography–tandem mass spectrometry: Application to SSADH deficiency". Journal of Inherited Metabolic Disease. 28 (6): 913–920. doi:10.1007/s10545-005-0111-0. ISSN 0141-8955. PMID 16435183. S2CID 9956364.
  4. Busardò FP, Jones AW (January 2015). "GHB pharmacology and toxicology: acute intoxication, concentrations in blood and urine in forensic cases and treatment of the withdrawal syndrome". Current Neuropharmacology. 13 (1): 47–70. doi:10.2174/1570159X13666141210215423. PMC 4462042. PMID 26074743.
  5. Felmlee MA, Morse BL, Morris ME (January 2021). "γ-Hydroxybutyric Acid: Pharmacokinetics, Pharmacodynamics, and Toxicology". The AAPS Journal. 23 (1): 22. doi:10.1208/s12248-020-00543-z. PMC 8098080. PMID 33417072.
  6. Taxon ES, Halbers LP, Parsons SM (May 2020). "Kinetics aspects of Gamma-hydroxybutyrate dehydrogenase". Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics. 1868 (5): 140376. doi:10.1016/j.bbapap.2020.140376. PMID 31981617.
  7. Kamal RM, van Noorden MS, Franzek E, Dijkstra BA, Loonen AJ, De Jong CA (March 2016). "The Neurobiological Mechanisms of Gamma-Hydroxybutyrate Dependence and Withdrawal and Their Clinical Relevance: A Review". Neuropsychobiology. 73 (2): 65–80. doi:10.1159/000443173. hdl:2066/158441. PMID 27003176.
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