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Record Information
Version1.0
Creation Date2016-09-30 22:26:39 UTC
Update Date2020-06-04 19:31:06 UTC
MCDB ID BMDB0000202
Secondary Accession Numbers
  • BMDB00202
Metabolite 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 exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Methylmalonic acid exists in all living species, ranging from bacteria to humans. In cattle, methylmalonic acid is involved in the metabolic pathway called the vitamin K metabolism pathway. Methylmalonic acid is a potentially toxic compound. Methylmalonic acid has been found to be associated with several diseases known as eosinophilic esophagitis, combined malonic and methylmalonic aciduria, alzheimer's disease, and methylmalonic aciduria mitochondrial encephelopathy leigh-like; also methylmalonic acid has been linked to the inborn metabolic disorders including vitamin B12 deficiency.
Structure
Thumb
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 Number516-05-2
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility679 mg/mLNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable 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
Synthesis ReferenceEdamura, Koji; Arai, Takeshi. Malonic and methylmalonic acids from b-hydroxypropionic acids. Jpn. Kokai Tokkyo Koho (1979), 5 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sun HZ, Shi K, Wu XH, Xue MY, Wei ZH, Liu JX, Liu HY: Lactation-related metabolic mechanism investigated based on mammary gland metabolomics and 4 biofluids' metabolomics relationships in dairy cows. BMC Genomics. 2017 Dec 2;18(1):936. doi: 10.1186/s12864-017-4314-1. [PubMed:29197344 ]
  2. Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]