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Record Information

Version

2.0

Creation Date

2012-05-31 13:48:30 -0600

Update Date

2015-09-13 12:56:10 -0600

Secondary Accession Numbers

ECMDB01259

Identification

Name:

Succinic acid semialdehyde

Description

Succinic 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

MOL SDF PDB SMILES InChI

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Straight 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 Framework

Aliphatic acyclic compounds

External Descriptors

aldehydic acid (CHEBI:16265 )
Fatty aldehydes (LMFA06000118 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	194 g/L	ALOGPS
logP	-0.47	ALOGPS
logP	-0.56	ChemAxon
logS	0.28	ALOGPS
pKa (Strongest Acidic)	4.13	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	22.61 m³·mol⁻¹	ChemAxon
Polarizability	9.26 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

4-aminobutanoate degradation I	PW002068
Propanoate metabolism	PW000940
arginine metabolism	PW000790
beta-Alanine metabolism	PW000896
ornithine metabolism	PW000791

KEGG Pathways:

Alanine, aspartate and glutamate metabolism ec00250
Butanoate metabolism ec00650
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Nicotinate and nicotinamide metabolism ec00760
Propanoate metabolism ec00640
Tyrosine metabolism ec00350
Valine, leucine and isoleucine degradation ec00280
Vitamin B6 metabolism ec00750
beta-Alanine metabolism ec00410

EcoCyc Pathways:

4-aminobutyrate degradation I PWY-6535
4-aminobutyrate degradation II PWY-6537

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9400000000-8e1cb554add6ed6c4e35	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9300000000-f5403e2e858fded273ac	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9400000000-8e1cb554add6ed6c4e35	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9300000000-f5403e2e858fded273ac	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9500000000-eb52f4d003b7d5b86b3d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9600000000-463f366ebd0be24a0283	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-d9618eb947af434dcf2f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fr-9800000000-40373963cdda851ebfea	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-bf9ebea7e4800559c111	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-0900000000-64b3498f7cdd4597da6a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0udi-1900000000-9d47aab2400f1da945bc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0udi-1900000000-94e1ac309574efbe3903	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0udi-3900000000-7ec96b67f820176c39d3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0udi-5900000000-7708b3a1c05b69363aa9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0zfr-8900000000-12726b727f621ac971b7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 7V, negative	splash10-0089-9000000000-9eb7dd16da8275702c75	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0udi-1900000000-567d38fac821ab993d19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-e31b8066f970e1c178d1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052u-9000000000-76526f6c67d7a67c1d07	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-70e85383e59b46bc429f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-5900000000-f1c2507387f92b6e1e3f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zgi-9400000000-ba1b880a90d3ace8beee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-971836bb1672ad33106e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052f-9000000000-06109e02fc0baa708cdc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-ce51d68c1c700db8f966	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-d171f37acc222eeea075	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9100000000-b23feac6075bc2594f5e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9000000000-aa34fb8bd9988d794431	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-101491882eb1be877e89	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View 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)

Links

External Links:

Resource	Link
CHEBI ID	16265
HMDB ID	HMDB01259
Pubchem Compound ID	1112
Kegg ID	C00232
ChemSpider ID	1080
Wikipedia	Succinic semialdehyde
BioCyc ID	SUCC-S-ALD
EcoCyc ID	SUCC-S-ALD
Ligand Expo	SSN

Enzymes

Protein Details

1. 4-aminobutyrate aminotransferase

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.

Protein Details

2. Succinate-semialdehyde dehydrogenase [NADP+]

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.

Protein Details

3. 4-aminobutyrate aminotransferase_

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.

Protein Details

4. Aldehyde dehydrogenase-like protein yneI

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.

Protein Details

5. Uncharacterized oxidoreductase yihU

General function:: Involved in 3-hydroxyisobutyrate dehydrogenase activity
Specific function:: Specific function unknown
Gene Name:: yihU
Uniprot ID:: P0A9V8
Molecular weight:: 31158

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Succinic acid semialdehyde (M2MDB000313)

Structure for #<Compound:0xace6c484>

Enzymes

Reactions

Reactions

Reactions

Reactions