Record Information
Version1.0
Creation date2011-09-21 00:04:56 UTC
Update date2019-11-26 03:21:00 UTC
Primary IDFDB021905
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. 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 the diseases such as methylmalonic aciduria mitochondrial encephelopathy leigh-like; methylmalonic acid has also been linked to several inborn metabolic disorders including transcobalamin II deficiency, cobalamin malabsorption, fumarase deficiency, and propionic acidemia.
CAS Number516-05-2
Structure
Thumb
Synonyms
SynonymSource
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
methyl-Malonatehmdb
methyl-Malonic acidhmdb
methyl-Propanedioatehmdb
methyl-Propanedioic acidhmdb
α-methylmalonateGenerator
α-methylmalonic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility149 g/LALOGPS
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
Chemical FormulaC4H6O4
IUPAC name2-methylpropanedioic acid
InChI IdentifierInChI=1S/C4H6O4/c1-2(3(5)6)4(7)8/h2H,1H3,(H,5,6)(H,7,8)
InChI KeyZIYVHBGGAOATLY-UHFFFAOYSA-N
Isomeric SMILESCC(C(O)=O)C(O)=O
Average Molecular Weight118.088
Monoisotopic Molecular Weight118.02660868
Classification
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
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Indirect biological role:

Physico-Chemical Properties - Experimental
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
EI-MSMass Spectrum (Electron Ionization)splash10-05di-9000000000-8d09b408489f7b1743b5Spectrum
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-9000000000-1578bea9a6b8b12e2f9bSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-05fr-9000000000-0e443f81ee9c6c9b1fa5Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0ab9-9100000000-d23d6a0a35141ed9a950Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-01b9-6900000000-6d969044a89f00e1b46fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-0f655174050263224e67Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0ab9-9000000000-26a654fb133b28a816a0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-7afd566e443d5fa38887Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-5c4795e954d5c3e9b74eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01b9-6900000000-6d969044a89f00e1b46fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-0f655174050263224e67Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ab9-9000000000-26a654fb133b28a816a0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-7afd566e443d5fa38887Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-5c4795e954d5c3e9b74eSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-175b62a78de8d2295d7cSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00dm-9100000000-2118d1ea1507076c595cSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0007-9000000000-5ead13e9a754843f3de4Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-04818c3d6cdaf0e910ebSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-ea4a508808f00639e8c2Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-9100000000-e8e132c8d454aa8a0490Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-5900000000-9b75ec910fa494f0ad6aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05di-9200000000-87a71ae13cf70d990bb1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9000000000-e7ae04912b5ee745a992Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-4900000000-0714f0bc5c29e5d61ac4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9100000000-ecfebddbd3d8f7224994Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-506ee5ec2100e13e09ceSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID473
ChEMBL IDCHEMBL1232416
KEGG Compound IDC02170
Pubchem Compound ID487
Pubchem Substance IDNot Available
ChEBI ID17453
Phenol-Explorer IDNot Available
DrugBank IDDB04183
HMDB IDHMDB00202
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDDXX
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMethylmalonic acid
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
EnzymesNot Available
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