Record Information
Version2.0
Creation Date2012-05-31 10:22:59 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00176
Identification
Name:Fumaric acid
DescriptionA precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. (wikipedia)
Structure
Thumb
Synonyms:
  • (2E)-But-2-enedioate
  • (2E)-But-2-enedioic acid
  • (E)-2-Butenedioate
  • (E)-2-Butenedioic acid
  • 2-(E)-Butenedioate
  • 2-(E)-Butenedioic acid
  • Allomaleate
  • Allomaleic acid
  • Boletate
  • Boletic acid
  • FC 33
  • Fum
  • Fumarate
  • Fumaric acid
  • Lichenate
  • Lichenic acid
  • Sodium fumarate
  • Sodium fumaric acid
  • Trans-1,2-Ethylenedicarboxylate
  • Trans-1,2-Ethylenedicarboxylic acid
  • Trans-2-Butenedioate
  • Trans-2-Butenedioic acid
  • Trans-Butenedioate
  • Trans-Butenedioic acid
Chemical Formula:C4H4O4
Weight:Average: 116.0722
Monoisotopic: 116.010958616
InChI Key:VZCYOOQTPOCHFL-OWOJBTEDSA-N
InChI:InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
CAS number:110-17-8
IUPAC Name:(2E)-but-2-enedioic acid
Traditional IUPAC Name:fumaric acid
SMILES:OC(=O)\C=C\C(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
  • 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
Physical Properties
State:Solid
Charge:-2
Melting point:549 °C
Experimental Properties:
PropertyValueSource
Water Solubility:7.0 mg/mL [US EPA (1981)]PhysProp
LogP:0.46 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility24.1 g/LALOGPS
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
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
L-Aspartic acid > Fumaric acid + Ammonia
Succinic acid + acceptor > Fumaric acid + reduced acceptor
L-Malic acid > Fumaric acid + Water
(2E,4Z,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + Water > 2-oxopent-4-enoate + Fumaric acid
Adenylsuccinic acid > Fumaric acid + Adenosine monophosphate
Succinic acid + Quinone <> Fumaric acid + Hydroquinone
2-Hydroxy-6-ketononadienedicarboxylate + Water + 2-Hydroxy-6-ketononatrienedioate <> Succinic acid + Fumaric acid
Adenylsuccinic acid + SAICAR <> Fumaric acid + Adenosine monophosphate + AICAR
L-Malic acid + L-Malic acid <> Fumaric acid + Water
Succinic acid + Ubiquinone-10 + FAD <> Fumaric acid + QH2 + FADH2
Succinic acid + Ubiquinone-1 > Ubiquinol-1 + Fumaric acid
Succinic acid + Ubiquinone-2 > Fumaric acid + Ubiquinol-2
Succinic acid + Ubiquinone-3 > Fumaric acid + Ubiquinol-3
Succinic acid + Ubiquinone-4 > Fumaric acid + Ubiquinol-4
Succinic acid + Ubiquinone-5 > Fumaric acid + Ubiquinol-5
Succinic acid + Ubiquinone-6 > Fumaric acid + Ubiquinol-6
Succinic acid + Ubiquinone-7 > Fumaric acid + Ubiquinol-7
Succinic acid + Ubiquinone-8 > Fumaric acid + Ubiquinol 8 + Ubiquinol-8
Succinic acid + Coenzyme Q9 > Fumaric acid + Ubiquinol-9
Succinic acid + Ubiquinone-10 > Fumaric acid + Ubiquinol-10 + Ubiquinol-10
Fumaric acid + Water > L-Malic acid + L-Malic acid
L-Aspartic acid + L-Aspartic acid > Fumaric acid + Ammonia
L-Aspartic acid + L-Aspartic acid > Fumaric acid + Ammonium
N(6)-(1,2-dicarboxyethyl)AMP > Fumaric acid + Adenosine monophosphate
Argininosuccinic acid > Fumaric acid + L-Arginine
SAICAR + SAICAR > AICAR + Fumaric acid
N(6)-(1,2-dicarboxyethyl)AMP + Adenylsuccinic acid > Fumaric acid + Adenosine monophosphate
2-Hydroxy-6-ketononatrienedioate + Water > Hydrogen ion + Fumaric acid + 2-Hydroxy-2,4-pentadienoate + 2-Hydroxy-2,4-pentadienoate
Ubiquinone-0 + Succinic acid > Ubiquinol-0 + Fumaric acid
Fumaric acid + 2 Hydrogen ion + a menaquinol > Succinic acid + a menaquinone
Fumaric acid + Water <> L-Malic acid
L-Malic acid <> Fumaric acid + Water
Succinic acid + FAD <> FADH2 + Fumaric acid
Succinic acid + Acceptor <> Fumaric acid + Reduced acceptor
Adenylsuccinic acid <> Adenosine monophosphate + Fumaric acid
SAICAR <> Fumaric acid + AICAR
4 4,5-Dihydroorotic acid + Fumaric acid <> Orotic acid + Succinic acid
Argininosuccinic acid <> L-Arginine + Fumaric acid
L-Aspartic acid <> Fumaric acid + Ammonia
L-Aspartic acid <> Hydrogen ion + Fumaric acid + Ammonia
Succinic acid + FAD <> FADH2 + Fumaric acid
Succinic acid + FAD <> FADH2 + Fumaric acid
4 4,5-Dihydroorotic acid + Fumaric acid <> Orotic acid + Succinic acid
More...

SMPDB Pathways:
2-Oxopent-4-enoate metabolismPW001890 ThumbThumb?image type=greyscaleThumb?image type=simple
2-Oxopent-4-enoate metabolism 2PW002035 ThumbThumb?image type=greyscaleThumb?image type=simple
Aspartate metabolismPW000787 ThumbThumb?image type=greyscaleThumb?image type=simple
L-glutamate metabolismPW000789 ThumbThumb?image type=greyscaleThumb?image type=simple
Nitrogen metabolismPW000755 ThumbThumb?image type=greyscaleThumb?image type=simple
Oxidative phosphorylationPW000919 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cyclePW000779 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-0)PW002023 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-10)PW001010 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-2)PW001002 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-3)PW001003 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-4)PW001004 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-5)PW001005 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-6)PW001006 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-7)PW001007 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-8)PW001008 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA cycle (ubiquinol-9)PW001009 ThumbThumb?image type=greyscaleThumb?image type=simple
arginine metabolismPW000790 ThumbThumb?image type=greyscaleThumb?image type=simple
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW000910 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 1435709748PW000960 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 2PW002033 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
115± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
255± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
267± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-04b277f233e1bd56c9afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-4900000000-99764eff7d7cb7bfaee3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-9000000000-453b921a0aaf64cfd558View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9000000000-cd7e7026d13bb5fe844bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00dj-9000000000-383c22a29e2769626c47View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ir3-9000000000-3013847e2e0f9bf18d29View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00di-9000000000-9cc4f29b523ed34dc0b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-00di-9000000000-d9885a6093f38dd8b9faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-00di-9000000000-46fdee94b5a787f1b81fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03k9-8900000000-3ff0fb725ec9dffc3688View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014m-9000000000-394fd8f1b59c7befec9dView 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-3d34cd791255c022876aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-55a5c43ec34fdd2cb0a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-9000000000-7c9639a65d534cd8ff97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-9000000000-c5eb63dc643f72e91edeView 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
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
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
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
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
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
  • Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Redjems-Bennani N, Jeandel C, Lefebvre E, Blain H, Vidailhet M, Gueant JL: Abnormal substrate levels that depend upon mitochondrial function in cerebrospinal fluid from Alzheimer patients. Gerontology. 1998;44(5):300-4. Pubmed: 9693263
  • Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Dong, Changsheng; Ma, Xinming. Method for preparation of fumaric acid from the tail gas acid spray solution from oxidation of phthalic anhydride. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 5pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID29806
HMDB IDHMDB00134
Pubchem Compound ID723
Kegg IDC00122
ChemSpider ID10197150
WikipediaFumaric acid
BioCyc IDFUM
EcoCyc IDFUM
Ligand ExpoFUM

Enzymes

General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
frdA
Uniprot ID:
P00363
Molecular weight:
65971
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in fumarate hydratase activity
Specific function:
(S)-malate = fumarate + H(2)O
Gene Name:
fumC
Uniprot ID:
P05042
Molecular weight:
50488
Reactions
(S)-malate = fumarate + H(2)O.
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
sdhB
Uniprot ID:
P07014
Molecular weight:
26770
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in catalytic activity
Specific function:
(S)-dihydroorotate + a quinone = orotate + a quinol
Gene Name:
pyrD
Uniprot ID:
P0A7E1
Molecular weight:
36774
Reactions
(S)-dihydroorotate + a quinone = orotate + a quinol.
General function:
Energy production and conversion
Specific function:
Seems to be involved in the anchoring of the catalytic components of the fumarate reductase complex to the cytoplasmic membrane
Gene Name:
frdC
Uniprot ID:
P0A8Q0
Molecular weight:
15015
General function:
Involved in fumarate metabolic process
Specific function:
Seems to be involved in the anchoring of the catalytic components of the fumarate reductase complex to the cytoplasmic membrane
Gene Name:
frdD
Uniprot ID:
P0A8Q3
Molecular weight:
13107
General function:
Involved in N6-(1,2-dicarboxyethyl)AMP AMP-lyase (fumarate-forming) activity
Specific function:
N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP
Gene Name:
purB
Uniprot ID:
P0AB89
Molecular weight:
51542
Reactions
N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP.
(S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate = fumarate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
General function:
Involved in lyase activity
Specific function:
It functions as an aerobic enzyme in the citric acid cycle. It accounts for about 80% of the fumarase activity when the bacteria grows aerobically
Gene Name:
fumA
Uniprot ID:
P0AC33
Molecular weight:
60298
Reactions
(S)-malate = fumarate + H(2)O.
General function:
Involved in aspartate ammonia-lyase activity
Specific function:
L-aspartate = fumarate + NH(3)
Gene Name:
aspA
Uniprot ID:
P0AC38
Molecular weight:
52356
Reactions
L-aspartate = fumarate + NH(3).
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
sdhA
Uniprot ID:
P0AC41
Molecular weight:
64421
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhD
Uniprot ID:
P0AC44
Molecular weight:
12867
General function:
Involved in electron carrier activity
Specific function:
Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth
Gene Name:
frdB
Uniprot ID:
P0AC47
Molecular weight:
27123
Reactions
Succinate + acceptor = fumarate + reduced acceptor.
General function:
Involved in FMN binding
Specific function:
Catalyzes the 6-electron oxidation of protoporphyrinogen-IX to form protoporphyrin-IX. Does not use oxygen directly. Is coupled to the respiratory chain
Gene Name:
hemG
Uniprot ID:
P0ACB4
Molecular weight:
21226
Reactions
Protoporphyrinogen IX + 3 menaquinone = protoporphyrin IX + 3 menaquinol.
General function:
Involved in electron carrier activity
Specific function:
Catalyzes the oxidation of L-aspartate to iminoaspartate
Gene Name:
nadB
Uniprot ID:
P10902
Molecular weight:
60337
Reactions
L-aspartate + O(2) = iminosuccinate + H(2)O(2).
General function:
Involved in argininosuccinate lyase activity
Specific function:
2-(N(omega)-L-arginino)succinate = fumarate + L-arginine
Gene Name:
argH
Uniprot ID:
P11447
Molecular weight:
50318
Reactions
2-(N(omega)-L-arginino)succinate = fumarate + L-arginine.
General function:
Involved in lyase activity
Specific function:
It functions in the generation of fumarate for use as an anaerobic electron acceptor
Gene Name:
fumB
Uniprot ID:
P14407
Molecular weight:
60105
Reactions
(S)-malate = fumarate + H(2)O.
General function:
Involved in succinate dehydrogenase activity
Specific function:
Membrane-anchoring subunit of succinate dehydrogenase (SDH)
Gene Name:
sdhC
Uniprot ID:
P69054
Molecular weight:
14299
General function:
Involved in catalytic activity
Specific function:
Catalyzes the cleavage of the C5-C6 bond of 2-hydroxy-6- oxononadienedioate and 2-hydroxy-6-oxononatrienedioate, a dienol ring fission product of the bacterial meta-cleavage pathway for degradation of phenylpropionic acid
Gene Name:
mhpC
Uniprot ID:
P77044
Molecular weight:
32585
Reactions
(2E,4Z)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + H(2)O = (2E)-2-hydroxypenta-2,4-dienoate + succinate.
(2E,4Z,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + H(2)O = (2E)-2-hydroxypenta-2,4-dienoate + fumarate.

Transporters

General function:
Involved in C4-dicarboxylate transmembrane transporter activity
Specific function:
Responsible for the transport of C4-dicarboxylates from the periplasm across the inner membrane
Gene Name:
dcuA
Uniprot ID:
P0ABN5
Molecular weight:
45750
General function:
Involved in C4-dicarboxylate transmembrane transporter activity
Specific function:
Responsible for the transport of C4-dicarboxylates from the periplasm across the inner membrane
Gene Name:
dcuB
Uniprot ID:
P0ABN9
Molecular weight:
47935
General function:
Involved in C4-dicarboxylate transmembrane transporter activity
Specific function:
Responsible for the transport of C4-dicarboxylates during anaerobic growth
Gene Name:
dcuC
Uniprot ID:
P0ABP3
Molecular weight:
48412
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in symporter activity
Specific function:
Responsible for the aerobic transport of the dicarboxylates fumarate, L- and D-malate and to a lesser extent succinate, from the periplasm across the inner membrane
Gene Name:
dctA
Uniprot ID:
P0A830
Molecular weight:
45436
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368