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Identification
YMDB IDYMDB01566
NameMalonate
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionMalonic acid, also known as malonate or H2MALO, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Malonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Malonic acid exists in all living species, ranging from bacteria to humans. Within yeast, malonic acid participates in a number of enzymatic reactions. In particular, malonic acid and acetic acid can be converted into acetoacetic acid through the action of the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In addition, malonic acid can be biosynthesized from malonyl-CoA; which is mediated by the enzyme fatty acid synthase. malonyl/acetyl transferase domain. In yeast, malonic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway.
Structure
Thumb
Synonyms
  • alpha,Omega-dicarboxylic acid
  • Carboxyacetic acid
  • Dicarboxylate
  • Dicarboxylic acid
  • Dicarboxymethane
  • H2Malo
  • HOOC-CH2-COOH
  • Kyselina malonova
  • Malonate
  • Malonate dicarboxylic acid
  • Malonic acid, 1,3-(14)C2-labeled
  • Malonic acid, 2-(14)C-labeled
  • Malonic acid, diammonium salt
  • Malonic acid, dipotassium salt
  • Malonic acid, disodium salt
  • Malonic acid, disodium salt, 1-(14)C-labeled
  • Malonic acid, dithallium salt
  • Malonic acid, monocalcium salt
  • Malonic acid, monosodium salt
  • Malonic acid, potassium salt
  • Malonic acid, sodium salt
  • Metahnedicarboxylic acid
  • Methanedicarbonic acid
  • Methanedicarboxylic acid
  • Propanedioate
  • Propanedioic acid
  • Propanedioic acid dithallium salt
  • Propanediolic acid
  • Thallium malonate
  • Thallous malonate
  • Dithallium malonate
  • Monosodium malonate
  • Malonic acid
CAS number141-82-2
WeightAverage: 104.0615
Monoisotopic: 104.010958616
InChI KeyOFOBLEOULBTSOW-UHFFFAOYSA-N
InChIInChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
IUPAC Namepropanedioic acid
Traditional IUPAC Namemalonic acid
Chemical FormulaC3H4O4
SMILESOC(=O)CC(O)=O
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
Charge0
Melting point135 °C
Experimental Properties
PropertyValueReference
Water Solubility763 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-0.81 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility197 g/LALOGPS
logP-0.6ALOGPS
logP-0.33ChemAxon
logS0.28ALOGPS
pKa (Strongest Acidic)2.43ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity18.99 m³·mol⁻¹ChemAxon
Polarizability8.13 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid biosynthesisec00061 Map00061
SMPDB Reactions
Malonate + Acetic acidAcetoacetic acid
butanoic acid + Malonate3-Oxohexanoic acid
hexanoic acid + Malonate3-Oxooctanoic acid
Caprylic acid + Malonate3-Oxodecanoic acid
capric acid + Malonate3-Oxododecanoic acid
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
1190 ± 60 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-1900000000-a1463432c138c328557dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-5e58241137fee0ccc64aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006t-9700000000-54976b3ce8f36ce0676dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4930000000-e7dbed4919870db8dabfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-05gl-1943000000-456e387fdf365bf0f8eeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-6c56a402111059603ba4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f239df8fdd12e9a74445JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-6865e83f0df5c9831619JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0900000000-a768f0aae86e17a3a6baJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1900000000-a1463432c138c328557dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-5e58241137fee0ccc64aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-9700000000-54976b3ce8f36ce0676dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-05gl-1943000000-456e387fdf365bf0f8eeJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-4930000000-e7dbed4919870db8dabfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-a45cfb1e2683f8ad8c5cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0911000000-8b0d7393c5dc4462a756JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfu-9300000000-cbc239877c485e6dff65JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9410000000-c30e36ba8e95ef1c83beJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9100000000-c7a1704f8a38ca2d245aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4l-9100000000-9fa84f43f2e19b56035cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052f-9100000000-8a21753b343cf5dabdcbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0006-9000000000-6c56a402111059603ba4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-f239df8fdd12e9a74445JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-3900000000-e0a4c7e792cfd0e60cc3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-4c03aa889e6a98ab532fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-9000000000-b3d14c986f292bdcf477JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-8e1041322f9acda4088aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-af4dccf21d68110099a1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-3900000000-e0a4c7e792cfd0e60cc3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-4c03aa889e6a98ab532fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-b3d14c986f292bdcf477JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-8e1041322f9acda4088aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-af4dccf21d68110099a1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-3900000000-2126168f67ddb43e544dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9000000000-e9d5906655e37a471b89JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-7900000000-795ca313c7daaf448edeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-9400000000-a6390568ef61fe1a284eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9100000000-cc17364c6d52c2c208f3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-6900000000-b1169abf90c9693f8e30JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-cec6a47ea3eb4a95a957JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-cffa3dea7855764ea854JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-dd4efef191376724d0f1JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID30794
HMDB IDHMDB00691
Pubchem Compound ID867
Kegg IDC00383
ChemSpider ID844
FOODB IDFDB008117
Wikipedia IDMalonic_acid
BioCyc IDMALONATE