Showing Compound Card for (S)-Methylmalonic acid semialdehyde (CDB005158)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (12) Show 13 proteinsXML
Record Information
Version1.0
Created at2020-04-17 19:15:10 UTC
Updated at2020-11-18 16:39:27 UTC
CannabisDB IDCDB005158
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. (S)-Methylmalonic acid semialdehyde is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(S)-Methylmalonate semialdehydeChEBI
(2S)-2-Methyl-3-oxopropanoateHMDB
(2S)-2-Methyl-3-oxopropanoic acidHMDB
Chemical FormulaC4H6O3
Average Molecular Weight102.09
Monoisotopic Molecular Weight102.0317
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
Disposition

Source:

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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrialALDH6A114q24.3Q02252 details
Aldehyde oxidaseAOX12q33Q06278 details
4-aminobutyrate aminotransferase, mitochondrialABAT16p13.2P80404 details
4-trimethylaminobutyraldehyde dehydrogenaseALDH9A11q23.1P49189 details
Alpha-aminoadipic semialdehyde dehydrogenaseALDH7A15q31P49419 details
Aldehyde dehydrogenase family 1 member A3ALDH1A315q26.3P47895 details
Aldehyde dehydrogenase, mitochondrialALDH212q24.2P05091 details
Fatty aldehyde dehydrogenaseALDH3A217p11.2P51648 details
Aldehyde dehydrogenase X, mitochondrialALDH1B19p11.1P30837 details
3-hydroxyacyl-CoA dehydrogenase type-2HSD17B10Xp11.2Q99714 details
Hydroxyacyl-coenzyme A dehydrogenase, mitochondrialHADH4q22-q26Q16836 details
3-hydroxyisobutyrate dehydrogenase, mitochondrialHIBADH7p15.2P31937 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Aldehyde oxidaseAOX12q33Q06278 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0002217
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Only showing the first 10 proteins. There are 13 proteins in total.

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Enzymes

Enzyme Details
1. Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial
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
Enzyme Details
2. Aldehyde oxidase
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Enzyme Details
3. 4-aminobutyrate aminotransferase, mitochondrial
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
Enzyme Details
4. 4-trimethylaminobutyraldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Enzyme Details
5. Alpha-aminoadipic semialdehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Enzyme Details
6. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Enzyme Details
7. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Enzyme Details
8. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Enzyme Details
9. Aldehyde dehydrogenase X, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Enzyme Details
10. 3-hydroxyacyl-CoA dehydrogenase type-2
General function:
Involved in oxidoreductase activity
Specific function:
Functions in mitochondrial tRNA maturation. Part of mitochondrial ribonuclease P, an enzyme composed of MRPP1/TRMT10C, MRPP2/HSD17B10 and MRPP3/KIAA0391, which cleaves tRNA molecules in their 5'-ends. By interacting with intracellular amyloid-beta, it may contribute to the neuronal dysfunction associated with Alzheimer disease (AD).
Gene Name:
HSD17B10
Uniprot ID:
Q99714
Molecular weight:
25983.695

Only showing the first 10 proteins. There are 13 proteins in total.

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