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Showing Compound (S)-Methylmalonic acid semialdehyde (FDB022912)

Record Information
Version1.0
Creation date2011-09-21 00:21:37 UTC
Update date2020-09-17 15:40:45 UTC
Primary IDFDB022912
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-Methylmalonic acid semialdehyde
Description(S)-Methylmalonic acid semialdehyde, also known as (2S)-2-methyl-3-oxopropanoate, 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. Within humans, (S)-methylmalonic acid semialdehyde participates in a number of enzymatic reactions. In particular, (S)-methylmalonic acid semialdehyde can be biosynthesized from (S)-3-hydroxyisobutyric acid; which is catalyzed by 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)-beta-aminoisobutyric acid and oxoglutaric acid; which is catalyzed by the enzyme 4-aminobutyrate aminotransferase, mitochondrial. In humans, (S)-methylmalonic acid semialdehyde is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. 2-Methyl-3-oxopropanoic acid with configuration S at the chiral centre.
CAS Number99043-16-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(S)-Methylmalonate semialdehydeChEBI
(2S)-2-Methyl-3-oxopropanoateHMDB
(2S)-2-Methyl-3-oxopropanoic acidHMDB
(2S)-2-methyl-3-oxopropanoatehmdb
(2S)-2-methyl-3-oxopropanoic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility266 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H6O3
IUPAC name(2S)-2-methyl-3-oxopropanoic acid
InChI IdentifierInChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)/t3-/m0/s1
InChI KeyVOKUMXABRRXHAR-VKHMYHEASA-N
Isomeric SMILESC[C@@H](C=O)C(O)=O
Average Molecular Weight102.0886
Monoisotopic Molecular Weight102.031694058
Classification
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
Disposition

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(S)-Methylmalonic acid semialdehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9000000000-8b181508e3ce65539b46Spectrum
Predicted GC-MS(S)-Methylmalonic acid semialdehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9600000000-15e42a2e09123d5f22adSpectrum
Predicted GC-MS(S)-Methylmalonic acid semialdehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zg0-9400000000-e46caa43ec4709ce76862015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-6c1632ad1d79839902622015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-6762a2cf4db52c84495c2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-9066dc83487b73946c992015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9200000000-8fde49823ba2083f055f2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-a320f14ddfc09e7989382015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0uk9-8900000000-0a76d84228c38b1cfe1d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9300000000-dd49ef94a8379e8517cd2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-4f42a2a7dc0b37e742da2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-b5c480248a004c0694162021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-6de8f6b91e5efd633c282021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-a0e9ace5e33e8c50915e2021-09-22View Spectrum
NMRNot Available
ChemSpider ID4575365
ChEMBL IDNot Available
KEGG Compound IDC06002
Pubchem Compound ID5462303
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02217
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34698
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
4-aminobutyrate aminotransferase, mitochondrialABATP80404
Pathways
NameSMPDB LinkKEGG Link
Propanoate MetabolismSMP00016 map00640
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference