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Identification
YMDB IDYMDB00236
NameSuccinic acid semialdehyde
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSuccinic acid semialdehyde, also known as 3-formylpropionic acid or 4-oxobutanoate, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Succinic acid semialdehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Succinic acid semialdehyde is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 2-formylpropionic acid ethyl ester
  • 3-Formylpropanoate
  • 3-Formylpropanoic acid
  • 3-Formylpropionic acid
  • 4-Oxobutanoate
  • 4-Oxobutanoic acid
  • beta-Formylpropionate
  • beta-Formylpropionic acid
  • Butanoic acid, 4-oxo- (9CI)
  • Butryaldehydate
  • Butryaldehydic acid
  • gamma-Oxybutyrate
  • gamma-Oxybutyric acid
  • Semi-aldehyde succinique
  • Semi-aldehyde succinique [French]
  • semialdehyde succinique
  • Succinaldehydate
  • Succinaldehydic acid
  • Succinate semialdehyde
  • Succinic acid semialdehyde
  • Succinic semialdehyde
  • 3-Formylpropionate
  • b-Formylpropionate
  • b-Formylpropionic acid
  • Β-formylpropionate
  • Β-formylpropionic acid
  • Succinic semialdehyde, calcium salt
CAS number692-29-5
WeightAverage: 102.0886
Monoisotopic: 102.031694058
InChI KeyUIUJIQZEACWQSV-UHFFFAOYSA-N
InChIInChI=1S/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)
IUPAC Name4-oxobutanoic acid
Traditional IUPAC Namesuccinic semialdehyde
Chemical FormulaC4H6O3
SMILES[H]OC(=O)C([H])([H])C([H])([H])C([H])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative Parents
Substituents
  • Straight chain fatty acid
  • Alpha-hydrogen aldehyde
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility194 g/LALOGPS
logP-0.47ALOGPS
logP-0.56ChemAxon
logS0.28ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity22.61 m³·mol⁻¹ChemAxon
Polarizability9.26 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
4-aminobutanoate degradationPW002382 ThumbThumb?image type=greyscaleThumb?image type=simple
Glutamate MetabolismPW002376 ThumbThumb?image type=greyscaleThumb?image type=simple
Tyrosine metabolismPW002441 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Alanine, aspartate and glutamate metabolismec00250 Map00250
Butanoate metabolismec00650 Map00650
Nicotinate and nicotinamide metabolismec00760 Map00760
Tyrosine metabolismec00350 Map00350
Vitamin B6 metabolismec00750 Map00750
SMPDB Reactions
4-(Glutamylamino) butanoate + Oxoglutaric acidL-Glutamic acid + Succinic acid semialdehyde
Succinic acid semialdehyde + water + NADPNADPH + Succinic acid + hydron
Succinic acid semialdehyde + NAD + waterSuccinic acid + NADH + hydron
gamma-Aminobutyric acid + Oxoglutaric acidL-Glutamic acid + Succinic acid semialdehyde
KEGG Reactions
Oxoglutaric acid + gamma-Aminobutyric acidL-Glutamic acid + Succinic acid semialdehyde
NADP + water + Succinic acid semialdehydeNADPH + hydron + Succinic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9400000000-8e1cb554add6ed6c4e35JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9300000000-f5403e2e858fded273acJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9400000000-8e1cb554add6ed6c4e35JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9300000000-f5403e2e858fded273acJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9500000000-eb52f4d003b7d5b86b3dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9600000000-463f366ebd0be24a0283JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-d9618eb947af434dcf2fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9800000000-40373963cdda851ebfeaJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-bf9ebea7e4800559c111JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-e31b8066f970e1c178d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-9000000000-76526f6c67d7a67c1d07JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-70e85383e59b46bc429fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-5900000000-f1c2507387f92b6e1e3fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zgi-9400000000-ba1b880a90d3ace8beeeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-971836bb1672ad33106eJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Ramos, F., el Guezzar, M., Grenson, M., Wiame, J. M. (1985). "Mutations affecting the enzymes involved in the utilization of 4-aminobutyric acid as nitrogen source by the yeast Saccharomyces cerevisiae." Eur J Biochem 149:401-404.3888627
  • Vissers, S., Andre, B., Muyldermans, F., Grenson, M. (1989). "Positive and negative regulatory elements control the expression of the UGA4 gene coding for the inducible 4-aminobutyric-acid-specific permease in Saccharomyces cerevisiae." Eur J Biochem 181:357-361.2653828
  • Coleman, S. T., Fang, T. K., Rovinsky, S. A., Turano, F. J., Moye-Rowley, W. S. (2001). "Expression of a glutamate decarboxylase homologue is required for normal oxidative stress tolerance in Saccharomyces cerevisiae." J Biol Chem 276:244-250.11031268
Synthesis Reference:Bruce, R.; Sims, K.; Pitts, F. N., Jr. Synthesis and purification of succinic semialdehyde. Analytical Biochemistry (1971), 41(1), 271-3.
External Links:
ResourceLink
CHEBI ID16265
HMDB IDHMDB01259
Pubchem Compound ID1112
Kegg IDC00232
ChemSpider ID1080
FOODB IDFDB022516
WikipediaSuccinic semialdehyde
BioCyc IDSUCC-S-ALD

Enzymes

General function:
Involved in transaminase activity
Specific function:
N(2)-acetyl-L-ornithine + 2-oxoglutarate = N- acetyl-L-glutamate 5-semialdehyde + L-glutamate
Gene Name:
ARG8
Uniprot ID:
P18544
Molecular weight:
46681.10156
Reactions
N(2)-acetyl-L-ornithine + 2-oxoglutarate → N-acetyl-L-glutamate 5-semialdehyde + L-glutamate.
General function:
Involved in oxidoreductase activity
Specific function:
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O = L-glutamate + NAD(P)H
Gene Name:
PUT2
Uniprot ID:
P07275
Molecular weight:
64434.60156
Reactions
(S)-1-pyrroline-5-carboxylate + NAD(P)(+) + 2 H(2)O → L-glutamate + NAD(P)H.
General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Required for the degradation of gamma-aminobutyric acid (GABA), which is important for utilization of GABA as nitrogen source and for oxidative stress tolerance. Deaminates GABA to succinate semialdehyde, which in turn is converted to succinate by the succinate-semialdehyde dehydrogenase UGA2. Cannot transaminate beta-alanine (BAL)
Gene Name:
UGA1
Uniprot ID:
P17649
Molecular weight:
52945.69922
Reactions
4-aminobutanoate + 2-oxoglutarate → succinate semialdehyde + L-glutamate.
General function:
Involved in oxidoreductase activity
Specific function:
Succinate semialdehyde + NAD(P)(+) + H(2)O = succinate + NAD(P)H
Gene Name:
UGA2
Uniprot ID:
P38067
Molecular weight:
54188.80078
Reactions
Succinate semialdehyde + NAD(P)(+) + H(2)O → succinate + NAD(P)H.