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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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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

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 , 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+

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 , 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

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]


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
Page generated by SRI International Pathway Tools version 18.5 on Thu Dec 18, 2014, BIOCYC14A.