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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:19:10 UTC
HMDB IDHMDB0000634
Secondary Accession Numbers
  • HMDB00634
Metabolite Identification
Common NameCitraconic acid
DescriptionMesaconic acid is one of several isomeric carboxylic acids obtained from citric acid. Is used as a fire retardant, recent studies revealed this acid is a competitive inhibitor of fumarate reduction.
Structure
Thumb
Synonyms
ValueSource
(Z)-2-Methyl-2-butenedioic acidChEBI
2-Methyl-2-butenedioic acidChEBI
2-Methylmaleic acidChEBI
alpha-Methylmaleic acidChEBI
cis-2-Methylbutenedioic acidChEBI
cis-Methylbutenedioic acidChEBI
CitraconsaeureChEBI
Methyl-maleinsaeureChEBI
Methylmaleic acidChEBI
(Z)-2-Methyl-2-butenedioateGenerator
CitraconateGenerator
2-Methyl-2-butenedioateGenerator
2-MethylmaleateGenerator
a-MethylmaleateGenerator
a-Methylmaleic acidGenerator
alpha-MethylmaleateGenerator
α-methylmaleateGenerator
α-methylmaleic acidGenerator
cis-2-MethylbutenedioateGenerator
cis-MethylbutenedioateGenerator
MethylmaleateGenerator
Citraconic acid, ammonium saltMeSH
Citraconic acid, calcium saltMeSH
Citraconic acid, sodium saltMeSH
Methylfumaric acidMeSH
(e)-2-Methyl-2-butenedioic acidMeSH
Citraconic acid, (e)-isomerMeSH
Mesaconic acidMeSH
MonomethylfumarateMeSH
Chemical FormulaC5H6O4
Average Molecular Weight130.0987
Monoisotopic Molecular Weight130.02660868
IUPAC Name(2Z)-2-methylbut-2-enedioic acid
Traditional Namecitraconic acid
CAS Registry Number498-23-7
SMILES
C\C(=C\C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-
InChI KeyHNEGQIOMVPPMNR-IHWYPQMZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point88 - 94 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility783 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.9 g/LALOGPS
logP0.21ALOGPS
logP0.35ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)2.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.96 m³·mol⁻¹ChemAxon
Polarizability11.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-053s-9830000000-9984d183d92e149a6ab4View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-9300000000-e6df22429c37d2a7f548View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053s-9830000000-9984d183d92e149a6ab4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1910000000-5eda2b2a1e8b0386b997View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01q3-9200000000-640fe5e61db043d72d25View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05g3-9540000000-ba938fe63ed9356955c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9100000000-707e9072305131e101d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-2a007e703ec5aa2df51aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000f-9200000000-5095d8b00331302fe65fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-2900000000-98ab39de610d4d7e428dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-1786e7db899e12344315View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-a1b543932fc265020973View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-d5dc2c9fdcd47f64c404View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-81b2f20752aef9eee2e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-000i-9200000000-ddad81eb9311ec64a8c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-2900000000-98ab39de610d4d7e428dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-1786e7db899e12344315View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-a1b543932fc265020973View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-d5dc2c9fdcd47f64c404View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-81b2f20752aef9eee2e9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-000i-9200000000-ddad81eb9311ec64a8c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-4900000000-86e2b44f3c8ee5a18c48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02g9-9200000000-6d6e041c039e8649caf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-7eeaf466a984bad3e0c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-6900000000-69d0c4409d2eb535ceebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-9400000000-a67e18d9101e6c4863ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ko-9100000000-6c212f68da0a408b4ea1View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.35-0.84 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.33-0.51 umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected and Quantified2.0 (1.2-2.6) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified2.2 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified1.6 (0.9-2.1) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022155
    KNApSAcK IDNot Available
    Chemspider ID553689
    KEGG Compound IDC02226
    BioCyc ID2-METHYLMALEATE
    BiGG IDNot Available
    Wikipedia LinkCitraconic_acid
    METLIN ID5607
    PubChem Compound643798
    PDB IDNot Available
    ChEBI ID17626
    References
    Synthesis ReferenceBerg, Rudolph G. Catalytic preparation of citraconic and itaconic acids. U.S. (1972), 5 pp.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Stoltz JF, Nicolas A: Study of amino groups of the human platelet membrane. Acta Haematol. 1978;60(5):304-9. [PubMed:101016 ]
    2. Alelu-Paz R, Iturrieta-Zuazo I, Byne W, Haroutunian V, Garcia-Villanueva M, Rabano A, Garcia-Amado M, Prensa L, Gimenez-Amaya JM: A new antigen retrieval technique for human brain tissue. PLoS One. 2008;3(10):e3378. doi: 10.1371/journal.pone.0003378. Epub 2008 Oct 13. [PubMed:18852880 ]