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Record Information
Version3.6
Creation Date2008-10-16 22:29:05 UTC
Update Date2016-02-11 01:20:10 UTC
HMDB IDHMDB11111
Secondary Accession Numbers
  • HMDB11666
Metabolite Identification
Common NameMalonic semialdehyde
DescriptionMalonic semialdehyde is formed in the alternative pathway of propionate metabolism and in the catabolism of beta-alanine. Studies done on these pathways in cultured cells from a patient with mitochondrial malonyl-CoA decarboxylase deficiency show that malonic semialdehyde is directly converted into acetyl-CoA in man. (PMID: 6418146 ).
Structure
Thumb
Synonyms
ValueSource
Formylacetic acidChEBI
FormylacetateGenerator
3-OxopropanoateHMDB
3-Oxopropanoic acidHMDB
3-Oxopropionic acidHMDB
Formyl acetateHMDB
Formyl acetic acidHMDB
Malonaldehydic acidHMDB
Malonate semialdehydeHMDB
Chemical FormulaC3H4O3
Average Molecular Weight88.0621
Monoisotopic Molecular Weight88.016043994
IUPAC Name3-oxopropanoic acid
Traditional Name3-oxopropanoic acid
CAS Registry Number926-61-4
SMILES
OC(=O)CC=O
InChI Identifier
InChI=1S/C3H4O3/c4-2-1-3(5)6/h2H,1H2,(H,5,6)
InChI KeyInChIKey=OAKURXIZZOAYBC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbonyl compounds
Sub Class1,3-dicarbonyl compounds
Direct Parent1,3-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility251.0 mg/mLALOGPS
logP-0.69ALOGPS
logP-0.49ChemAxon
logS0.46ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity18.06 m3·mol-1ChemAxon
Polarizability7.27 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-60b5c86a7fc98a3aad0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9000000000-3c3b0812b6c639b6f784View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-1cdf7a37f821d563d842View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-bdca8db935b372ea8814View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-9000000000-12b3bc39c58c4350baaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-ad063699951a4021dc2aView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Aspartate MetabolismSMP00067map00250
Beta-Alanine MetabolismSMP00007map00410
Canavan DiseaseSMP00175Not Available
Carnosinuria, carnosinemiaSMP00493Not Available
GABA-Transaminase DeficiencySMP00351Not Available
HypoacetylaspartiaSMP00192Not Available
Malonic AciduriaSMP00198Not Available
Malonyl-coa decarboxylase deficiencySMP00502Not Available
Methylmalonic Aciduria Due to Cobalamin-Related DisordersSMP00201Not Available
Propanoate MetabolismSMP00016map00640
Ureidopropionase deficiencySMP00492Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027893
KNApSAcK IDNot Available
Chemspider ID845
KEGG Compound IDC00222
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11111
Metagene LinkHMDB11111
METLIN IDNot Available
PubChem Compound868
PDB IDNot Available
ChEBI ID17960
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Scholem RD, Brown GK: Metabolism of malonic semialdehyde in man. Biochem J. 1983 Oct 15;216(1):81-5. [6418146 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:
ALDH6A1
Uniprot ID:
Q02252
Molecular weight:
57839.31
Reactions
Malonic semialdehyde + Coenzyme A + NAD(P)(+) → Acetyl-CoA + CO(2) + NAD(P)Hdetails
Malonic semialdehyde + Coenzyme A + NAD → Acetyl-CoA + Carbon dioxide + NADH + Hydrogen Iondetails
Malonic semialdehyde + Coenzyme A + NADP → Acetyl-CoA + Carbon dioxide + NADPH + Hydrogen Iondetails
Malonic semialdehyde + Coenzyme A + NADP → Malonyl-CoA + NADPH + Hydrogen Iondetails
General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-alanine.
Gene Name:
ABAT
Uniprot ID:
P80404
Molecular weight:
56438.405
Reactions
Beta-Alanine + Oxoglutaric acid → Malonic semialdehyde + L-Glutamic aciddetails