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MetaCyc Compound: succinate semialdehyde

Synonyms: succinyl semialdehyde, succ-S-ald, succinic semialdehyde

Chemical Formula: C4H5O3

Molecular Weight: 101.08 Daltons

Monoisotopic Molecular Weight: 102.0316940589 Daltons

succinate semialdehyde compound structure

SMILES: C([CH]=O)CC(=O)[O-]

InChI: InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)/p-1

InChIKey: InChIKey=UIUJIQZEACWQSV-UHFFFAOYSA-M

Unification Links: CAS:692-29-5 , ChEBI:57706 , ChemSpider:7822211 , HMDB:HMDB01259 , IAF1260:34331 , KEGG:C00232 , MetaboLights:MTBLC57706 , PubChem:9543238

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -59.216465 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

3-hydroxypropanoate/4-hydroxybutanate cycle :
4-hydroxybutanoate + NADP+succinate semialdehyde + NADPH + H+

4-aminobutyrate degradation I , 4-aminobutyrate degradation IV , GABA shunt :
succinate semialdehyde + NAD+ + H2O → succinate + NADH + 2 H+

4-aminobutyrate degradation II , 4-hydroxyphenylacetate degradation , nicotine degradation I , nicotine degradation II , TCA cycle IV (2-oxoglutarate decarboxylase) :
succinate semialdehyde + NADP+ + H2O → succinate + NADPH + 2 H+

4-aminobutyrate degradation III :
succinate semialdehyde + NAD(P)+ + H2O → succinate + NAD(P)H + 2 H+

L-glutamate degradation IV :
4-hydroxybutanoate + NAD(P)+succinate semialdehyde + NAD(P)H + H+
succinate semialdehyde + NAD+ + H2O → succinate + NADH + 2 H+

Reactions known to produce the compound:

3-hydroxypropanoate/4-hydroxybutanate cycle , succinate fermentation to butyrate :
succinate semialdehyde + coenzyme A + NADP+ ← succinyl-CoA + NADPH + H+

4-hydroxyphenylacetate degradation :
2-keto-4-hydroxypimelate → succinate semialdehyde + pyruvate

nicotine degradation I :
4-methylaminobutanoate + H2O + oxygen → succinate semialdehyde + methylamine + hydrogen peroxide

nicotine degradation II , nicotine degradation V :
6-hydroxy-3-succinoyl-pyridine + 2 NADH + oxygen + 2 H+ → 2,5-dihydroxypyridine + succinate semialdehyde + 2 NAD+ + H2O

TCA cycle IV (2-oxoglutarate decarboxylase) :
2-oxoglutarate + H+succinate semialdehyde + CO2

vitamin B6 degradation :
2-(acetamidomethylene)succinate + H+ + 2 H2O → ammonium + CO2 + succinate semialdehyde + acetate

Not in pathways:
2-oxoglutarate + 4-hydroxybutanoate → succinate semialdehyde + (R)-2-hydroxyglutarate

Reactions known to both consume and produce the compound:

4-aminobutyrate degradation I , 4-aminobutyrate degradation II , 4-aminobutyrate degradation III , GABA shunt , nicotine degradation I :
4-aminobutanoate + 2-oxoglutarate ↔ succinate semialdehyde + L-glutamate

4-aminobutyrate degradation IV :
4-aminobutanoate + pyruvate ↔ succinate semialdehyde + L-alanine

4-aminobutyrate degradation V :
4-hydroxybutanoate + NAD+succinate semialdehyde + NADH + H+
4-aminobutanoate + 2-oxoglutarate ↔ succinate semialdehyde + L-glutamate

L-glutamate degradation IV :
4-aminobutanoate + 2-oxoglutarate ↔ succinate semialdehyde + L-glutamate
4-aminobutanoate + pyruvate ↔ succinate semialdehyde + L-alanine

succinate fermentation to butyrate :
4-hydroxybutanoate + NAD+succinate semialdehyde + NADH + H+

Not in pathways:
4-aminobutanoate + glyoxylate ↔ succinate semialdehyde + glycine

In Reactions of unknown directionality:

Not in pathways:
2,4-dihydroxyhept-2-enedioate = succinate semialdehyde + pyruvate

Enzymes inhibited by succinate semialdehyde, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: 4-hydroxy-tetrahydrodipicolinate synthase [Blickling97, Karsten97] , NAD(P)+-dependent 3-sulfopropanal dehydrogenase [Mayer09] , N-carbamoylsarcosine amidohydrolase [Zajc96]

This compound has been characterized as an alternative substrate of the following enzymes: α-ketoglutarate semialdehyde dehydrogenase , L-glutamate γ-semialdehyde dehydrogenase , α-ketoglutaric semialdehyde dehydrogenase


References

Blickling97: Blickling S, Renner C, Laber B, Pohlenz HD, Holak TA, Huber R (1997). "Reaction mechanism of Escherichia coli dihydrodipicolinate synthase investigated by X-ray crystallography and NMR spectroscopy." Biochemistry 36(1);24-33. PMID: 8993314

Karsten97: Karsten WE (1997). "Dihydrodipicolinate synthase from Escherichia coli: pH dependent changes in the kinetic mechanism and kinetic mechanism of allosteric inhibition by L-lysine." Biochemistry 36(7);1730-9. PMID: 9048556

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Mayer09: Mayer J, Cook AM (2009). "Homotaurine Metabolized to 3-Sulfopropanoate in Cupriavidus necator H16: Enzymes and Genes in a Patchwork Pathway." J Bacteriol. PMID: 19648235

Zajc96: Zajc A, Romao MJ, Turk B, Huber R (1996). "Crystallographic and fluorescence studies of ligand binding to N-carbamoylsarcosine amidohydrolase from Arthrobacter sp." J Mol Biol 263(2);269-83. PMID: 8913306


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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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