| Revision as of 13:10, 15 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 472665883 of page Succinic_semialdehyde for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 14:33, 11 December 2024 edit Marbletan (talk | contribs)Extended confirmed users5,452 edits no longer a stub |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 470483179 |
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| verifiedrevid = 476998916 |
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|ImageFile=succinic semialdehyde.png |
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| ImageFile =succinic semialdehyde.png |
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|ImageSize=180px |
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| ImageSize =180px |
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|IUPACName=4-oxobutanoic acid |
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| PIN =4-Oxobutanoic acid |
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|OtherNames= |
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| OtherNames = |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C00232 |
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| KEGG = C00232 |
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| InChI = 1/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7) |
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| InChI = 1/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = UIUJIQZEACWQSV-UHFFFAOYSA-N |
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| StdInChIKey = UIUJIQZEACWQSV-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = <!-- blanked - oldvalue: 692-29-5 --> |
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| CASNo =692-29-5 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=1112 |
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| UNII = M73BX3CPMU |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem =1112 |
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⚫ |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 1080 |
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| ChemSpiderID = 1080 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 16265 |
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| ChEBI = 16265 |
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| SMILES = O=CCCC(=O)O |
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| SMILES = O=CCCC(=O)O |
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| MeSHName=Succinic+semialdehyde |
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| MeSHName =Succinic+semialdehyde |
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}} |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>4</sub>H<sub>6</sub>O<sub>3</sub> |
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| Formula =C<sub>4</sub>H<sub>6</sub>O<sub>3</sub> |
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| MolarMass=102.089 g/mol |
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| MolarMass =102.089 g/mol |
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| Appearance=oil |
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| Appearance =oil |
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| Density= |
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| Density = |
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| MeltingPt= |
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| MeltingPt = |
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| BoilingPtC = 135 |
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| BoilingPt= 135 °C at 14 ] |
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| Solubility=soluble in water, ], ], ]<ref name="hand"> |
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| BoilingPt_notes = at 14 ] |
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| Solubility =soluble in water, ], ], ]<ref name="hand"> |
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{{Citation |
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{{Citation |
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| last = Lide |
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| last = Lide |
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| first = David R. |
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| first = David R. |
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| author-link = |
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| first2 = |
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| publication-date = |
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| date = |
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| year = 1998 |
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| year = 1998 |
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| title = Handbook of Chemistry and Physics |
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| title = Handbook of Chemistry and Physics |
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| edition = 87 |
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| edition = 87 |
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| volume = |
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| volume = |
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| series = |
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| series = |
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| publication-place = Boca Raton, FL |
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| location = Boca Raton, Florida |
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| place = |
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| publisher = CRC Press |
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| publisher = CRC Press |
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| id = |
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| pages = 3–446 |
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| pages = 3–446 |
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}}</ref> |
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}} |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| MainHazards = |
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| FlashPt= |
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| FlashPt = |
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| AutoignitionPt = |
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| Autoignition= |
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'''Succinic semialdehyde''' (SSA) is a ] and ] metabolite. It is formed from GABA by the action of ] (4-aminobutyrate aminotransferase) and further ] to become ], which enters ]. SSA is oxidized into succinic acid by the enzyme ], which uses ] as a ].<ref>{{Cite journal |last1=Peng |first1=Qi |last2=Yang |first2=Min |last3=Wang |first3=Wei |last4=Han |first4=Lili |last5=Wang |first5=Guannan |last6=Wang |first6=Pengyue |last7=Zhang |first7=Jie |last8=Song |first8=Fuping |date=2014-12-20 |title=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 |journal=BMC Microbiology |volume=14 |issue=1 |pages=306 |doi=10.1186/s12866-014-0306-3 |issn=1471-2180 |pmc=4279683 |pmid=25527261 |doi-access=free }}</ref> <ref name=":0">{{Cite journal |last1=Struys |first1=E. A. |last2=Jansen |first2=E. E. W. |last3=Gibson |first3=K. M. |last4=Jakobs |first4=C. |date=December 2005 |title=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 |url=https://onlinelibrary.wiley.com/doi/10.1007/s10545-005-0111-0 |journal=Journal of Inherited Metabolic Disease |language=en |volume=28 |issue=6 |pages=913–920 |doi=10.1007/s10545-005-0111-0 |pmid=16435183 |s2cid=9956364 |issn=0141-8955}}</ref> When the oxidation of succinic semialdehyde to succinic acid is impaired, accumulation of succinic semialdehyde takes place which leads to ].<ref name=":0" /> |
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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).<ref name="pmid26074743">{{cite journal |vauthors=Busardò FP, Jones AW |title=GHB pharmacology and toxicology: acute intoxication, concentrations in blood and urine in forensic cases and treatment of the withdrawal syndrome |journal=Current Neuropharmacology |volume=13 |issue=1 |pages=47–70 |date=January 2015 |pmid=26074743 |pmc=4462042 |doi=10.2174/1570159X13666141210215423}}</ref><ref name="pmid33417072">{{cite journal |vauthors=Felmlee MA, Morse BL, Morris ME |title=γ-Hydroxybutyric Acid: Pharmacokinetics, Pharmacodynamics, and Toxicology |journal=The AAPS Journal |volume=23 |issue=1 |pages=22 |date=January 2021 |pmid=33417072 |pmc=8098080 |doi=10.1208/s12248-020-00543-z}}</ref><ref name="pmid31981617">{{cite journal |vauthors=Taxon ES, Halbers LP, Parsons SM |title=Kinetics aspects of Gamma-hydroxybutyrate dehydrogenase |journal= Biochimica et Biophysica Acta (BBA) - Proteins and Proteomics|volume=1868 |issue=5 |pages=140376 |date=May 2020 |pmid=31981617 |doi=10.1016/j.bbapap.2020.140376|doi-access=free }}</ref><ref name="pmid27003176">{{cite journal |vauthors=Kamal RM, van Noorden MS, Franzek E, Dijkstra BA, Loonen AJ, De Jong CA |title=The Neurobiological Mechanisms of Gamma-Hydroxybutyrate Dependence and Withdrawal and Their Clinical Relevance: A Review |journal=Neuropsychobiology |volume=73 |issue=2 |pages=65–80 |date=March 2016 |pmid=27003176 |doi=10.1159/000443173|hdl=2066/158441 |hdl-access=free }}</ref> |
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==See also== |
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* ] (aminotransferase) |
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* ] |
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==References== |
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{{Reflist}} |
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