Record Information
Version2.0
Creation Date2012-05-31 13:48:30 -0600
Update Date2015-09-13 12:56:10 -0600
Secondary Accession Numbers
  • ECMDB01259
Identification
Name:Succinic acid semialdehyde
DescriptionSuccinic acid semialdehyde is an intermediate in the catabolism of gamma-aminobutyrate (PMID 16435183). Succinate semialdehyde dehydrogenase is an enzyme that catalyses the reaction of succinate semialdehyde and NAD+ to form succinate and NADH.
Structure
Thumb
Synonyms:
  • 2-Formylpropionate ethyl ester
  • 2-Formylpropionic acid ethyl ester
  • 3-Formylpropanoate
  • 3-Formylpropanoic acid
  • 4-Oxobutanoate
  • 4-Oxobutanoic acid
  • b-Formylpropionate
  • b-Formylpropionic acid
  • Beta-Formylpropionate
  • Beta-Formylpropionic acid
  • Butryaldehydate
  • Butryaldehydic acid
  • g-Oxybutyrate
  • g-Oxybutyric acid
  • Gamma-Oxybutyrate
  • Gamma-Oxybutyric acid
  • Succ-S-ald
  • Succinaldehydate
  • Succinaldehydic acid
  • Succinate semialdehyde
  • Succinic acid semialdehyde
  • Succinic semialdehyde
  • Succinyl semialdehyde
  • β-Formylpropionate
  • β-Formylpropionic acid
  • γ-Oxybutyrate
  • γ-Oxybutyric acid
Chemical Formula:C4H6O3
Weight:Average: 102.0886
Monoisotopic: 102.031694058
InChI Key:UIUJIQZEACWQSV-UHFFFAOYSA-N
InChI:InChI=1S/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)
CAS number:692-29-5
IUPAC Name:4-oxobutanoic acid
Traditional IUPAC Name:succinic semialdehyde
SMILES:OC(=O)CCC=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
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Reactions:
Water + NADP + Succinic acid semialdehyde >2 Hydrogen ion + NADPH + Succinic acid
gamma-Aminobutyric acid + alpha-Ketoglutarate <> L-Glutamate + Succinic acid semialdehyde
Water + NAD + Succinic acid semialdehyde >2 Hydrogen ion + NADH + Succinic acid
Hydrogen ion + NADH + Succinic acid semialdehyde <> gamma-Hydroxybutyrate + NAD
Succinic acid semialdehyde + NAD + Water <> Succinic acid + NADH + Hydrogen ion
Succinic acid semialdehyde + NADP + Water <> Succinic acid + NADPH + Hydrogen ion
NAD + gamma-Hydroxybutyrate <> Hydrogen ion + NADH + Succinic acid semialdehyde
Oxoglutaric acid + gamma-Aminobutyric acid <> L-Glutamate + Succinic acid semialdehyde
Water + NAD + Succinic acid semialdehyde > Hydrogen ion + NADH + Succinic acid
Succinic acid semialdehyde + NADP + Water > Succinic acid + NADPH + Hydrogen ion
Succinic acid semialdehyde + NADP + Water > Succinic acid + NADPH
gamma-Aminobutyric acid + Oxoglutaric acid > Succinic acid semialdehyde + L-Glutamate
Succinic acid semialdehyde + NAD(P)(+) + Water > Succinic acid + NAD(P)H
Succinic acid semialdehyde + NAD + NADP + Water <> Succinic acid + NADH + NADPH +2 Hydrogen ion
4-Hydroxybutanoic acid + NAD <> Succinic acid semialdehyde + NADH + Hydrogen ion
gamma-Aminobutyric acid + Oxoglutaric acid > Succinic acid semialdehyde + L-Glutamic acid + L-Glutamate
Succinic acid semialdehyde + Water + NADP > NADPH +2 Hydrogen ion + Succinic acid + NADPH
Water + NADP + Succinic acid semialdehyde >2 Hydrogen ion + NADPH + Succinic acid
gamma-Aminobutyric acid + alpha-Ketoglutarate <> L-Glutamate + Succinic acid semialdehyde
gamma-Aminobutyric acid + alpha-Ketoglutarate <> L-Glutamate + Succinic acid semialdehyde
SMPDB Pathways:
4-aminobutanoate degradation IPW002068 ThumbThumb?image type=greyscaleThumb?image type=simple
Propanoate metabolismPW000940 ThumbThumb?image type=greyscaleThumb?image type=simple
arginine metabolismPW000790 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW000896 ThumbThumb?image type=greyscaleThumb?image type=simple
ornithine metabolismPW000791 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9400000000-8e1cb554add6ed6c4e35View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9300000000-f5403e2e858fded273acView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9400000000-8e1cb554add6ed6c4e35View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9300000000-f5403e2e858fded273acView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9500000000-eb52f4d003b7d5b86b3dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9600000000-463f366ebd0be24a0283View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-d9618eb947af434dcf2fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9800000000-40373963cdda851ebfeaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-bf9ebea7e4800559c111View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-e31b8066f970e1c178d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-9000000000-76526f6c67d7a67c1d07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-70e85383e59b46bc429fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-5900000000-f1c2507387f92b6e1e3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zgi-9400000000-ba1b880a90d3ace8beeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-971836bb1672ad33106eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Du L, Musson DG, Wang AQ: High turbulence liquid chromatography online extraction and tandem mass spectrometry for the simultaneous determination of suberoylanilide hydroxamic acid and its two metabolites in human serum. Rapid Commun Mass Spectrom. 2005;19(13):1779-87. Pubmed: 15945019
  • Du L, Musson DG, Wang AQ: Stability studies of vorinostat and its two metabolites in human plasma, serum and urine. J Pharm Biomed Anal. 2006 Nov 16;42(5):556-64. Epub 2006 Jul 5. Pubmed: 16824724
  • Hinshelwood A, McGarvie G, Ellis EM: Substrate specificity of mouse aldo-keto reductase AKR7A5. Chem Biol Interact. 2003 Feb 1;143-144:263-9. Pubmed: 12604212
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Knerr I, Gibson KM, Jakobs C, Pearl PL: Neuropsychiatric morbidity in adolescent and adult succinic semialdehyde dehydrogenase deficiency patients. CNS Spectr. 2008 Jul;13(7):598-605. Pubmed: 18622364
  • Lee BC, Choe YS, Chi DY, Paik JY, Lee KH, Choi Y, Kim BT: 8-cyclopentadienyltricarbonyl 99mtc 8-oxooctanoic acid: a novel radiotracer for evaluation of medium chain fatty acid metabolism in the liver. Bioconjug Chem. 2004 Jan-Feb;15(1):121-7. Pubmed: 14733591
  • Parise RA, Holleran JL, Beumer JH, Ramalingam S, Egorin MJ: A liquid chromatography-electrospray ionization tandem mass spectrometric assay for quantitation of the histone deacetylase inhibitor, vorinostat (suberoylanilide hydroxamicacid, SAHA), and its metabolites in human serum. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Aug 18;840(2):108-15. Epub 2006 May 24. Pubmed: 16725386
  • Struys, E. A., Jansen, E. E., Gibson, K. M., Jakobs, C. (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." J Inherit Metab Dis 28:913-920. Pubmed: 16435183
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Bruce, R.; Sims, K.; Pitts, F. N., Jr. Synthesis and purification of succinic semialdehyde. Analytical Biochemistry (1971), 41(1), 271-3.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16265
HMDB IDHMDB01259
Pubchem Compound ID1112
Kegg IDC00232
ChemSpider ID1080
WikipediaSuccinic semialdehyde
BioCyc IDSUCC-S-ALD
EcoCyc IDSUCC-S-ALD
Ligand ExpoSSN

Enzymes

General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
4-aminobutanoate + 2-oxoglutarate = succinate semialdehyde + L-glutamate
Gene Name:
gabT
Uniprot ID:
P22256
Molecular weight:
45774
Reactions
4-aminobutanoate + 2-oxoglutarate = succinate semialdehyde + L-glutamate.
(S)-3-amino-2-methylpropanoate + 2-oxoglutarate = 2-methyl-3-oxopropanoate + L-glutamate.
General function:
Involved in oxidoreductase activity
Specific function:
Succinate semialdehyde + NAD(P)(+) + H(2)O = succinate + NAD(P)H
Gene Name:
gabD
Uniprot ID:
P25526
Molecular weight:
51720
Reactions
Succinate semialdehyde + NADP(+) + H(2)O = succinate + NADPH.
General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Involved in the breakdown of putrescine via transamination of gamma-aminobutyrate
Gene Name:
puuE
Uniprot ID:
P50457
Molecular weight:
44729
Reactions
4-aminobutanoate + 2-oxoglutarate = succinate semialdehyde + L-glutamate.
General function:
Involved in oxidoreductase activity
Specific function:
Specific function unknown
Gene Name:
yneI
Uniprot ID:
P76149
Molecular weight:
49717
Reactions
Succinate semialdehyde + NAD(P)(+) + H(2)O = succinate + NAD(P)H.
General function:
Involved in 3-hydroxyisobutyrate dehydrogenase activity
Specific function:
Specific function unknown
Gene Name:
yihU
Uniprot ID:
P0A9V8
Molecular weight:
31158