Record Information
Version1.0
Creation date2010-04-08 22:07:56 UTC
Update date2018-01-23 19:01:20 UTC
Primary IDFDB008117
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePropanedioic acid
DescriptionMalonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionised form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's ethyl ester. The name originates from Latin malum, meaning apple. Malonic acid is the archetypal example of a competitive inhibitor: it acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain.; Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionised form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's ethyl ester. The name originates from the Greek word ????? (malon) meaning 'apple'. Propanedioic acid is found in many foods, some of which are green bell pepper, red bell pepper, common beet, and sweet orange.
CAS Number141-82-2
Structure
Thumb
Synonyms
SynonymSource
H2MaloChEBI
HOOC-CH2-COOHChEBI
Propanedioic acidChEBI
PropanedioateGenerator
MalonateGenerator
alpha,Omega-dicarboxylic acidHMDB
Carboxyacetic acidHMDB
DicarboxylateHMDB
Dicarboxylic acidHMDB
DicarboxymethaneHMDB
Kyselina malonovaHMDB
Malonate dicarboxylic acidHMDB
Metahnedicarboxylic acidHMDB
Methanedicarbonic acidHMDB
Methanedicarboxylic acidHMDB
Propanedioic acid dithallium saltHMDB
Propanediolic acidHMDB
Thallium malonateHMDB
Malonic acid, 2-(14)C-labeledHMDB
Malonic acid, monocalcium saltHMDB
Malonic acid, 1,3-(14)C2-labeledHMDB
Malonic acid, diammonium saltHMDB
Malonic acid, disodium saltHMDB
Malonic acid, dithallium saltHMDB
Malonic acid, dipotassium saltHMDB
Malonic acid, disodium salt, 1-(14)C-labeledHMDB
Malonic acid, monosodium saltHMDB
Malonic acid, potassium saltHMDB
Malonic acid, sodium saltHMDB
Thallous malonateHMDB
Dithallium malonateHMDB
Monosodium malonateHMDB
Malonic acidGenerator
1,3-Propanedioic acidbiospider
Malonic acid, 8CIdb_source
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
Chemical FormulaC3H4O4
IUPAC namepropanedioic acid
InChI IdentifierInChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
InChI KeyOFOBLEOULBTSOW-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC(O)=O
Average Molecular Weight104.0615
Monoisotopic Molecular Weight104.010958616
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 34.63%; H 3.87%; O 61.50%DFC
Melting PointMp 135.6°DFC
Boiling PointNot Available
Experimental Water Solubility763 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-0.81HANSCH,C ET AL. (1995)
Experimental pKapKa2 5.7 (25°,H2O)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-1900000000-a1463432c138c328557dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0900000000-5e58241137fee0ccc64aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006t-9700000000-54976b3ce8f36ce0676dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-001i-4930000000-e7dbed4919870db8dabfView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-05gl-1943000000-456e387fdf365bf0f8eeView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-6c56a402111059603ba4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-f239df8fdd12e9a74445View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-6865e83f0df5c9831619View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0900000000-a768f0aae86e17a3a6baView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1900000000-a1463432c138c328557dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-5e58241137fee0ccc64aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-9700000000-54976b3ce8f36ce0676dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-05gl-1943000000-456e387fdf365bf0f8eeView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-4930000000-e7dbed4919870db8dabfView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0900000000-a45cfb1e2683f8ad8c5cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0911000000-8b0d7393c5dc4462a756View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfu-9300000000-cbc239877c485e6dff65View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9410000000-c30e36ba8e95ef1c83beView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9100000000-c7a1704f8a38ca2d245aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4l-9100000000-9fa84f43f2e19b56035cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052f-9100000000-8a21753b343cf5dabdcbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0006-9000000000-6c56a402111059603ba4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-f239df8fdd12e9a74445View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-3900000000-e0a4c7e792cfd0e60cc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-4c03aa889e6a98ab532fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4l-9000000000-b3d14c986f292bdcf477View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-8e1041322f9acda4088aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-af4dccf21d68110099a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-3900000000-e0a4c7e792cfd0e60cc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-4c03aa889e6a98ab532fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9000000000-b3d14c986f292bdcf477View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-8e1041322f9acda4088aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-af4dccf21d68110099a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0006-3900000000-2126168f67ddb43e544dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-9000000000-e9d5906655e37a471b89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-7900000000-795ca313c7daaf448edeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-9400000000-a6390568ef61fe1a284eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9100000000-cc17364c6d52c2c208f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-6900000000-b1169abf90c9693f8e30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9300000000-cec6a47ea3eb4a95a957View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-cffa3dea7855764ea854View in MoNA
MSMass Spectrum (Electron Ionization)splash10-01ox-9000000000-dd4efef191376724d0f1View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID844
ChEMBL IDCHEMBL7942
KEGG Compound IDC04025
Pubchem Compound ID867
Pubchem Substance IDNot Available
ChEBI ID30794
Phenol-Explorer IDNot Available
DrugBank IDDB02175
HMDB IDHMDB00691
CRC / DFC (Dictionary of Food Compounds) IDDCG89-D:DCG89-D
EAFUS IDNot Available
Dr. Duke IDMALONIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001193
HET IDMLA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMalonic 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 / Bioactivities
DescriptorIDDefinitionReference
irritantDUKE
Enzymes
NameGene NameUniProt ID
4-aminobutyrate aminotransferase, mitochondrialABATP80404
Proto-oncogene tyrosine-protein kinase SrcSRCP12931
Pathways
NameSMPDB LinkKEGG Link
Aspartate MetabolismSMP00067 map00250
Fatty Acid BiosynthesisSMP00456 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.