Succinic acid semialdehyde (YMDB00236)

Identification

YMDB ID

YMDB00236

Name

Succinic acid semialdehyde

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Succinic 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

MOL SDF PDB SMILES InChI

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 number

692-29-5

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)

IUPAC Name

4-oxobutanoic acid

Traditional IUPAC Name

succinic semialdehyde

Chemical Formula

C₄H₆O₃

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.

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

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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

Organoleptic Properties

Not Available

SMPDB Pathways

4-aminobutanoate degradation	PW002382
Glutamate Metabolism	PW002376
Tyrosine metabolism	PW002441

KEGG Pathways

Alanine, aspartate and glutamate metabolism	ec00250
Butanoate metabolism	ec00650
Nicotinate and nicotinamide metabolism	ec00760
Tyrosine metabolism	ec00350
Vitamin B6 metabolism	ec00750

SMPDB Reactions

KEGG Reactions

Oxoglutaric acid + gamma-Aminobutyric acid → L-Glutamic acid + Succinic acid semialdehyde

NADP + water + Succinic acid semialdehyde → NADPH + hydron + Succinic acid

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

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

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:

Resource	Link
CHEBI ID	16265
HMDB ID	HMDB01259
Pubchem Compound ID	1112
Kegg ID	C00232
ChemSpider ID	1080
FOODB ID	FDB022516
Wikipedia	Succinic semialdehyde
BioCyc ID	SUCC-S-ALD

Enzymes

Protein Details

1. Acetylornithine aminotransferase, mitochondrial

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.

Protein Details

2. Delta-1-pyrroline-5-carboxylate dehydrogenase, mitochondrial

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.

Protein Details

3. 4-aminobutyrate aminotransferase

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.

Protein Details

4. 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:: UGA2
Uniprot ID:: P38067
Molecular weight:: 54188.80078

Reactions

Succinate semialdehyde + NAD(P)(+) + H(2)O → succinate + NAD(P)H.

Structure for #<Compound:0xa208aec4>

Enzymes

Reactions

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Reactions

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