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Record Information

Version

2.0

Creation Date

2012-05-31 13:57:34 -0600

Update Date

2015-06-03 15:54:19 -0600

Secondary Accession Numbers

ECMDB03015

Identification

Name:

Malonic semialdehyde

Description

Malonic semialdehyde is formed in the alternative pathway of propionate metabolism and in the catabolism of beta-alanine.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

3-Oxopropanoate
3-Oxopropanoic acid
3-Oxopropionate
3-Oxopropionic acid
Formyl acetate
Formyl acetic acid
Formylacetate
Formylacetic acid
Malonaldehydate
Malonaldehydic acid
Malonate semialdehyde
Malonate-S-ald
Malonic acid semialdehyde
Malonic acid-S-ald
Malonic semialdehyde

Chemical Formula:

C₃H₄O₃

Weight:

Average: 88.0621
Monoisotopic: 88.016043994

InChI Key:

OAKURXIZZOAYBC-UHFFFAOYSA-N

InChI:

InChI=1S/C3H4O3/c4-2-1-3(5)6/h2H,1H2,(H,5,6)

CAS number:

926-61-4

IUPAC Name:

3-oxopropanoic acid

Traditional IUPAC Name:

3-oxopropanoic acid

SMILES:

OC(=O)CC=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,3-dicarbonyl compounds. These are carbonyl compounds with the generic formula O=C(R)C(H)C(R')=O, where R and R' can be any group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

1,3-dicarbonyl compounds

Alternative Parents

Substituents

1,3-dicarbonyl compound
Alpha-hydrogen aldehyde
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

aldehydic acid (CHEBI:17960 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	251 g/L	ALOGPS
logP	-0.69	ALOGPS
logP	-0.49	ChemAxon
logS	0.46	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	-7.2	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	2	ChemAxon
Refractivity	18.06 m³·mol⁻¹	ChemAxon
Polarizability	7.27 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:

Propanoate metabolism	PW000940
Pyrimidine metabolism	PW000942
Uracil degradation III	PW002026
beta-Alanine metabolism	PW000896

KEGG Pathways:

Chloroalkane and chloroalkene degradation ec00625
Inositol phosphate metabolism ec00562
Microbial metabolism in diverse environments ec01120
Propanoate metabolism ec00640
Pyrimidine metabolism ec00240
beta-Alanine metabolism ec00410

EcoCyc Pathways:

uracil degradation III PWY0-1471

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-af40c902eb15697860c1	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00dv-9400000000-22ee45c5b87f3f02ca9c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-60b5c86a7fc98a3aad0c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9000000000-3c3b0812b6c639b6f784	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dl-9000000000-1cdf7a37f821d563d842	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-bdca8db935b372ea8814	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kf-9000000000-12b3bc39c58c4350baaa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-ad063699951a4021dc2a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-95d56443f4ea3bb3e226	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-066u-9000000000-d51b6071e071006aea6d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-47f01d70ed657922be53	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-87bbaed151efac084591	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-87bbaed151efac084591	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-6a46f602b8aa1b7b70b5	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

References

References:

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
Scholem RD, Brown GK: Metabolism of malonic semialdehyde in man. Biochem J. 1983 Oct 15;216(1):81-5. Pubmed: 6418146

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	17960
HMDB ID	HMDB11111
Pubchem Compound ID	868
Kegg ID	C00222
ChemSpider ID	845
Wikipedia ID	Not Available
BioCyc ID	MALONATE-S-ALD
EcoCyc ID	MALONATE-S-ALD

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. 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

3. Putative NADH dehydrogenase/NAD(P)H nitroreductase rutE

General function:: Involved in oxidoreductase activity
Specific function:: Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:: rutE
Uniprot ID:: P75894
Molecular weight:: 21570

Reactions

3-hydroxypropanoate + NADP(+) = 3-oxopropanoate + NADPH.

Protein Details

4. NADP-dependent L-serine/L-allo-threonine dehydrogenase ydfG

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADP-dependent oxidation of L-allo- threonine to L-2-amino-3-keto-butyrate, which is spontaneously decarboxylated into aminoacetone. Also acts on L-serine, D-serine, D-threonine, D-3-hydroxyisobutyrate, L-3-hydroxyisobutyrate, D- glycerate and L-glycerate
Gene Name:: ydfG
Uniprot ID:: P39831
Molecular weight:: 27249

Reactions

3-hydroxypropanoate + NADP(+) = 3-oxopropanoate + NADPH.

Protein Details

5. Protein rutD

General function:: Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:: Makes part of the rut operon, which is required for the utilization of pyrimidines as sole nitrogen source
Gene Name:: rutD
Uniprot ID:: P75895
Molecular weight:: 28898

Reactions

(Z)-3-aminoacrylate + H(2)O = malonate semialdehyde + NH(3).

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Malonic semialdehyde (M2MDB000474)

Structure for #<Compound:0xa7cdedd8>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions