P. aeruginosa Metabolome Database: Malonic semialdehyde (PAMDB000474)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000474

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 View Structure

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

Average Molecular Weight:

88.0621

Monoisotopic Molecular Weight:

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

Taxonomy Description

This compound 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

Organooxygen compounds

Class

Carbonyl compounds

Sub Class

1,3-dicarbonyl 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
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	251.0 mg/mL	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:

Hydrogen ion + Malonic semialdehyde + NADPH > 3-Hydroxypropanoate + NADP
3-Aminoacrylate + Hydrogen ion + Water > Malonic semialdehyde + Ammonium
beta-Alanine + alpha-Ketoglutarate <> Malonic semialdehyde + L-Glutamate
3-Aminoacrylate + Water <> Malonic semialdehyde + Ammonia
3-Hydroxypropanoate + NADP > Malonic semialdehyde + NADPH

Pathways:

Chloroalkane and chloroalkene degradation pae00625
Inositol phosphate metabolism pae00562
Microbial metabolism in diverse environments pae01120
Propanoate metabolism pae00640
Pyrimidine metabolism pae00240
beta-Alanine metabolism pae00410

Spectra

Spectra:

Spectrum Type	Description	Splash Key
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

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

Malonic semialdehyde (PAMDB000474)

Structure for Malonic semialdehyde (PAMDB000474)