Showing metabocard for (S)-Methylmalonic acid semialdehyde (BMDB0002217)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:52:48 UTC
Update Date2020-05-21 16:28:46 UTC
BMDB IDBMDB0002217
Secondary Accession Numbers
  • BMDB02217
Metabolite Identification
Common Name(S)-Methylmalonic acid semialdehyde
Description(S)-Methylmalonic acid semialdehyde, also known as (s)-methylmalonic acid semialdehyde, 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 (S)-Methylmalonic acid semialdehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (S)-Methylmalonic acid semialdehyde exists in all living organisms, ranging from bacteria to humans (S)-Methylmalonic acid semialdehyde participates in a number of enzymatic reactions, within cattle. In particular, (S)-Methylmalonic acid semialdehyde can be biosynthesized from (S)-3-hydroxyisobutyric acid through the action of the enzymes 3-hydroxyisobutyrate dehydrogenase, mitochondrial and enoyl-CoA hydratase, mitochondrial. In addition, (S)-Methylmalonic acid semialdehyde and L-glutamic acid can be biosynthesized from (S)-b-aminoisobutyric acid and oxoglutaric acid through the action of the enzyme 4-aminobutyrate aminotransferase, mitochondrial. In cattle, (S)-methylmalonic acid semialdehyde is involved in the metabolic pathway called the valine, leucine, and isoleucine degradation pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-Methylmalonate semialdehydeChEBI
(2S)-2-Methyl-3-oxopropanoateHMDB
(2S)-2-Methyl-3-oxopropanoic acidHMDB
Chemical FormulaC4H6O3
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
IUPAC Name(2S)-2-methyl-3-oxopropanoic acid
Traditional Name(S)-methylmalonaldehydic acid
CAS Registry Number99043-16-0
SMILES
C[C@@H](C=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)/t3-/m0/s1
InChI KeyVOKUMXABRRXHAR-VKHMYHEASA-N
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct Parent1,3-dicarbonyl compounds
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • 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
logP0ALOGPS
logP0.053ChemAxon
logS0.42ALOGPS
pKa (Strongest Acidic)3.98ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.64 m³·mol⁻¹ChemAxon
Polarizability9.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9000000000-8b181508e3ce65539b46View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9600000000-15e42a2e09123d5f22adView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-9400000000-e46caa43ec4709ce7686View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-6c1632ad1d7983990262View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-6762a2cf4db52c84495cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-9066dc83487b73946c99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-8fde49823ba2083f055fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-a320f14ddfc09e798938View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-8900000000-0a76d84228c38b1cfe1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9300000000-dd49ef94a8379e8517cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-4f42a2a7dc0b37e742daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-b5c480248a004c069416View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-6de8f6b91e5efd633c28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-a0e9ace5e33e8c50915eView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0002217
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022912
KNApSAcK IDNot Available
Chemspider ID4575365
KEGG Compound IDC06002
BioCyc IDCH3-MALONATE-S-ALD
BiGG ID34698
Wikipedia LinkNot Available
METLIN ID6553
PubChem Compound5462303
PDB IDNot Available
ChEBI ID27821
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial
General function:
Energy production and conversion
Specific function:
Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:
ALDH6A1
Uniprot ID:
Q07536
Molecular weight:
58063.0
Reactions
(S)-Methylmalonic acid semialdehyde + Water + NAD + Coenzyme A → Propionyl-CoA + NADH + Hydrogen carbonatedetails
Enzyme Details
2. 4-aminobutyrate aminotransferase, mitochondrial
General function:
Amino acid transport and metabolism
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 (By similarity).
Gene Name:
ABAT
Uniprot ID:
Q9BGI0
Molecular weight:
56731.0
Reactions
(S)-b-aminoisobutyric acid + Oxoglutaric acid → (S)-Methylmalonic acid semialdehyde + L-Glutamic aciddetails
Enzyme Details
3. Aldehyde oxidase 1
General function:
Nucleotide transport and metabolism
Specific function:
Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide, N-methylphthalazinium and phthalazine, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Is probably involved in the regulation of reactive oxygen species homeostasis. May be a prominent source of superoxide generation via the one-electron reduction of molecular oxygen. Also may catalyze nitric oxide (NO) production via the reduction of nitrite to NO with NADH or aldehyde as electron donor. May play a role in adipogenesis.
Gene Name:
AOX1
Uniprot ID:
P48034
Molecular weight:
147611.0
Reactions
(S)-Methylmalonic acid semialdehyde + Water + Oxygen → Methylmalonic acid + Hydrogen peroxidedetails
Enzyme Details
4. Aldehyde dehydrogenase, mitochondrial
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P20000
Molecular weight:
56653.0
Reactions
(S)-Methylmalonic acid semialdehyde + NAD + Water → Methylmalonic acid + NADHdetails