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Record Information
Version1.0
Creation Date2016-07-13 19:41:26 UTC
Update Date2016-07-20 20:49:18 UTC
LmdbLMDB00057
Secondary Accession NumbersNone
Metabolite Identification
Common NameFumaric acid
DescriptionFumaric acid is a dicarboxylic acid. It is a precursor to L-malate in the Krebs tricarboxylic acid (TCA) cycle. It is formed by the oxidation of succinic acid by succinate dehydrogenase. Fumarate is converted by the enzyme fumarase to malate. Fumaric acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by fumarate.
Structure
Thumb
Synonyms
ValueSource
(2E)-2-Butenedioic acidChEBI
(e)-2-Butenedioic acidChEBI
e297ChEBI
FumarsaeureChEBI
trans-1,2-Ethylenedicarboxylic acidChEBI
trans-But-2-enedioic acidChEBI
trans-Butenedioic acidChEBI
(2E)-2-ButenedioateGenerator
(e)-2-ButenedioateGenerator
trans-1,2-EthylenedicarboxylateGenerator
trans-But-2-enedioateGenerator
trans-ButenedioateGenerator
FumarateGenerator
(2E)-But-2-enedioateHMDB
(2E)-But-2-enedioic acidHMDB
2-(e)-ButenedioateHMDB
2-(e)-Butenedioic acidHMDB
AllomaleateHMDB
Allomaleic acidHMDB
BoletateHMDB
Boletic acidHMDB
FC 33HMDB
LichenateHMDB
Lichenic acidHMDB
Sodium fumarateHMDB
trans-2-ButenedioateHMDB
trans-2-Butenedioic acidHMDB
FuramagHMDB
Ammonium fumarateHMDB
Magnesium fumarateHMDB
MafusolHMDB
Chemical FormulaC4H4O4
Average Molecular Weight116.0722
Monoisotopic Molecular Weight116.010958616
IUPAC Name(2E)-but-2-enedioic acid
Traditional Namefumaric acid
CAS Registry Number110-17-8
SMILES
OC(=O)\C=C\C(O)=O
InChI Identifier
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
InChI KeyVZCYOOQTPOCHFL-OWOJBTEDSA-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
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • 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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.21ALOGPS
logP-0.041ChemAxon
logS-0.68ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.61 m³·mol⁻¹ChemAxon
Polarizability9.35 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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-2940000000-e988056514d4ce4acc27View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-2960000000-a5ebaf2bbade922838ecView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-0002-2950000000-32afa4d45e0e72b174b4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0950000000-fe0f05c02c783d0b6f6bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-006t-9530000000-0fc03f31f09dc8dbf4c6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0002-3690000000-75089756992cdbe841e3View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9100000000-2cf649749b42cc0c610cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-0890000000-b1c35cd55deb81254f66View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2940000000-e988056514d4ce4acc27View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2960000000-a5ebaf2bbade922838ecView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-2950000000-32afa4d45e0e72b174b4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0950000000-fe0f05c02c783d0b6f6bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-006t-9530000000-0fc03f31f09dc8dbf4c6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0002-3690000000-75089756992cdbe841e3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0940000000-177fdb9168659029ffaaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ba-9200000000-52f88e04bac0ff8cdf17View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-8920000000-06da44f348d0fe0358b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9100000000-57f13cd433a6fe4bf0b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0229-9600000000-cd9e2979d0bb1e2a62f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-03k9-8900000000-dc50dbf8a50872383d54View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0002-9100000000-b47e534bc82a6ed36e7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9800000000-dbf34563376daeb2901fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-9200000000-113bf08cdc77707ed3adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9000000000-f32d7ec65e8649bc2b0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-408d53a9fff7acc8ca23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6900000000-f149e9e5a34e27dd4d4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxt-9000000000-cae5f71dc27daaf17d9eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0092-9000000000-003dd2d9303272b2ebeaView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C 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 LocationsNot Available
Biofluid Locations and Tissue Locations
  • Brain
  • Colostrum
  • Feces
  • Jejunum
  • Kidney perfusate
  • Meat
  • Milk
  • Plasma
  • Ruminal Fluid
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
BrainDetected but not QuantifiedNot ApplicableNot AvailableOvine details
ColostrumDetected but not QuantifiedNot ApplicableNot AvailableBovine details
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
JejunumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
Kidney perfusateDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MeatDetected and Quantified107.37 +/- 14.42 uMNot AvailableBovine details
MeatDetected and Quantified123.02 +/- 19.31 uMNot AvailableBovine details
MeatDetected and Quantified160.89 +/- 17.1 uMNot AvailableBovine details
MeatDetected and Quantified84.76 +/- 11.89 uMNot AvailableBovine details
MeatDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected and Quantified7-23 uMNot AvailableBovine details
MilkDetected and Quantified2-81 uMNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
Ruminal FluidDetected and Quantified1.42 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified1.64 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified5.82 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified6.44 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified7.5 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified7.5 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified8.8 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified8.8 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified11.2 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified11.2 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified11.7 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified11.7 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified11 +/- 4 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified12 +/- 4 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified4 +/- 3.0 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified8 +/- 2 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified9 +/- 4 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified9 +/- 4 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified23.8 +/- 4.2 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified25.1 +/- 4.0 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified28.5 +/- 8.7 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified266 +/- 49 uMNot AvailableCaprine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
SerumDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
UrineDetected and Quantified127 umol/mmol creatinineNot AvailablePorcine details
UrineDetected and Quantified62 umol/mmol creatinineNot AvailablePorcine details
DrugBank IDDB01677
HMDB IDHMDB0000134
FooDB IDFDB008113
Phenol Explorer IDNot Available
KNApSAcK IDC00001183
BiGG ID33938
BioCyc IDFUM
METLIN ID3242
PDB IDNot Available
Wikipedia LinkFumaric_Acid
Chemspider ID10197150
ChEBI ID18012
PubChem Compound ID444972
Kegg Compound IDC00122
YMDB IDYMDB00101
ECMDB IDECMDB00176
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available