Showing Compound Card for Methylmalonic acid (CDB006354)

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Record Information
Version1.0
Created at2020-09-11 16:08:17 UTC
Updated at2022-12-13 23:36:28 UTC
CannabisDB IDCDB006354
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMethylmalonic acid
DescriptionMethylmalonic acid, also known as 2-methylmalonate or methyl-propanedioate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Methylmalonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Methylmalonic acid exists in all living species, ranging from bacteria to humans. Within humans, methylmalonic acid participates in a number of enzymatic reactions. In particular, methylmalonic acid and hydrogen peroxide can be biosynthesized from (S)-methylmalonic acid semialdehyde; which is catalyzed by the enzyme aldehyde oxidase. In addition, methylmalonic acid can be biosynthesized from (S)-methylmalonic acid semialdehyde; which is mediated by the enzyme aldehyde dehydrogenase, mitochondrial. In humans, methylmalonic acid is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. A dicarboxylic acid that is malonic acid in which one of the methylene hydrogens is substituted by a methyl group. Outside of the human body, Methylmalonic acid has been detected, but not quantified in, milk (cow). This could make methylmalonic acid a potential biomarker for the consumption of these foods. Methylmalonic acid is a potentially toxic compound. Methylmalonic acid, with regard to humans, has been found to be associated with several diseases such as cobalamin f disease (cblf) and methylmalonic aciduria, cblb type; methylmalonic acid has also been linked to several inborn metabolic disorders including cobalamin malabsorption, malonyl-coa decarboxylase deficiency, and propionic acidemia.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,1-Ethanedicarboxylic acidChEBI
2-Methylmalonic acidChEBI
alpha-Methylmalonic acidChEBI
Isosuccinic acidChEBI
1,1-EthanedicarboxylateGenerator
2-MethylmalonateGenerator
a-MethylmalonateGenerator
a-Methylmalonic acidGenerator
alpha-MethylmalonateGenerator
Α-methylmalonateGenerator
Α-methylmalonic acidGenerator
IsosuccinateGenerator
MethylmalonateGenerator
Methyl-malonateHMDB
Methyl-malonic acidHMDB
Methyl-propanedioateHMDB
Methyl-propanedioic acidHMDB
MethylpropanedioateHMDB
Methylpropanedioic acidHMDB
Acid, methylmalonicHMDB
Methylmalonic acidKEGG
Chemical FormulaC4H6O4
Average Molecular Weight118.088
Monoisotopic Molecular Weight118.02660868
IUPAC Name2-methylpropanedioic acid
Traditional Namemethylmalonic acid
CAS Registry NumberNot Available
SMILES
CC(C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)
InChI KeyZIYVHBGGAOATLY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.17ALOGPS
logP0.21ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)2.48ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.56 m³·mol⁻¹ChemAxon
Polarizability10.06 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-05di-9000000000-8d09b408489f7b1743b52014-09-20View Spectrum
GC-MSMethylmalonic acid, 2 TMS, GC-MS Spectrumsplash10-0002-1910000000-cf95dd8a481761a28664Spectrum
GC-MSMethylmalonic acid, 2 TMS, GC-MS Spectrumsplash10-006t-8900000000-4d8795e7e4300cc7ceffSpectrum
GC-MSMethylmalonic acid, 2 TMS, GC-MS Spectrumsplash10-00lr-5940000000-56b86ada220d335ce30aSpectrum
GC-MSMethylmalonic acid, 3 TMS, GC-MS Spectrumsplash10-001i-9301000000-54e5247d046de566ac1eSpectrum
GC-MSMethylmalonic acid, non-derivatized, GC-MS Spectrumsplash10-004i-9000000000-b9ee59dddf90dfc7c461Spectrum
GC-MSMethylmalonic acid, non-derivatized, GC-MS Spectrumsplash10-0002-1910000000-cf95dd8a481761a28664Spectrum
GC-MSMethylmalonic acid, non-derivatized, GC-MS Spectrumsplash10-006t-8900000000-4d8795e7e4300cc7ceffSpectrum
GC-MSMethylmalonic acid, non-derivatized, GC-MS Spectrumsplash10-001i-9301000000-54e5247d046de566ac1eSpectrum
GC-MSMethylmalonic acid, non-derivatized, GC-MS Spectrumsplash10-00lr-5940000000-56b86ada220d335ce30aSpectrum
GC-MSMethylmalonic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-684a11ce99cccbd9194aSpectrum
Predicted GC-MSMethylmalonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0g4i-9400000000-baa4ea6d613ebb8bffc7Spectrum
Predicted GC-MSMethylmalonic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dr-9310000000-a99f1bb4adbde62446d9Spectrum
Predicted GC-MSMethylmalonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethylmalonic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethylmalonic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSMethylmalonic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9000000000-1578bea9a6b8b12e2f9b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-05fr-9000000000-0e443f81ee9c6c9b1fa52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0ab9-9100000000-d23d6a0a35141ed9a9502012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-01b9-6900000000-6d969044a89f00e1b46f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-0f655174050263224e672012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0ab9-9000000000-26a654fb133b28a816a02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-7afd566e443d5fa388872012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-5c4795e954d5c3e9b74e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01b9-6900000000-6d969044a89f00e1b46f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-0f655174050263224e672017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ab9-9000000000-26a654fb133b28a816a02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-7afd566e443d5fa388872017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-5c4795e954d5c3e9b74e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-175b62a78de8d2295d7c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00dm-9100000000-2118d1ea1507076c595c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0007-9000000000-5ead13e9a754843f3de42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-04818c3d6cdaf0e910eb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-ea4a508808f00639e8c22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9100000000-e8e132c8d454aa8a04902021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-5900000000-9b75ec910fa494f0ad6a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05di-9200000000-87a71ae13cf70d990bb12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-e7ae04912b5ee745a9922016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4900000000-0714f0bc5c29e5d61ac42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9100000000-ecfebddbd3d8f72249942016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-506ee5ec2100e13e09ce2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.000348 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.000343 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.000213 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.000251 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.000274 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.000200 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0000202
DrugBank IDDB04183
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021905
KNApSAcK IDNot Available
Chemspider ID473
KEGG Compound IDC02170
BioCyc IDCPD-546
BiGG IDNot Available
Wikipedia LinkMethylmalonic_acid
METLIN ID3712
PubChem Compound487
PDB IDNot Available
ChEBI ID30860
References
General ReferencesNot Available