fumarate (PAMDB110748)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110748
Identification
Name: fumarate
Description:A C4-dicarboxylate that is the E-isomer of but-2-enedioate(2−)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • fum
  • fumaric acid
Chemical Formula: C4H2O4
Average Molecular Weight: 114.06
Monoisotopic Molecular Weight: 116.0109586168
InChI Key: VZCYOOQTPOCHFL-OWOJBTEDSA-L
InChI: InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/p-2/b2-1+
CAS number: 110-17-8
IUPAC Name:(2E)-but-2-enedioate
Traditional IUPAC Name: fumaric acid
SMILES:C(C([O-])=O)=CC(=O)[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct Parent Dicarboxylic 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
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
  • dicarboxylic acid dianion, C4-dicarboxylate (CHEBI:36180)
  • a C4-dicarboxylate (MALEATE)
Physical Properties
State: Solid
Charge:-2
Melting point: 549 °C
Experimental Properties:
PropertyValueReference
Melting Point549 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.0 mg/mLNot Available
LogP0.46HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility24.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity24.61 m3·mol-1ChemAxon
Polarizability9.35 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
caldariellaquinone + succinate → caldariellaquinol + fumarate
ETR-Quinones + succinate → ETR-Quinols + fumarate
canavaninosuccinate → L-canavanine + fumarate
Pathways:
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)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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
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, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0092-9000000000-003dd2d9303272b2ebeaView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Coustou V, Biran M, Besteiro S, Rivière L, Baltz T, Franconi JM, Bringaud F (2006)Fumarate is an essential intermediary metabolite produced by the procyclic Trypanosoma brucei. The Journal of biological chemistry 281, Pubmed: 16857679
  • Brekke E, Walls AB, Nørfeldt L, Schousboe A, Waagepetersen HS, Sonnewald U (2012)Direct measurement of backflux between oxaloacetate and fumarate following pyruvate carboxylation. Glia 60, Pubmed: 22052553
  • Salek RM, Maguire ML, Bentley E, Rubtsov DV, Hough T, Cheeseman M, Nunez D, Sweatman BC, Haselden JN, Cox RD, Connor SC, Griffin JL (2007)A metabolomic comparison of urinary changes in type 2 diabetes in mouse, rat, and human. Physiological genomics 29, Pubmed: 17190852
  • Ashrafian H, Czibik G, Bellahcene M, Aksentijevic D, Smith AC, Mitchell SJ, Dodd MS, Kirwan J, Byrne JJ, Ludwig C, Isackson H, Yavari A, Støttrup NB, Contractor H, Cahill TJ, Sahgal N, Ball DR, Birkler RI, Hargreaves I, Tennant DA, Land J, Lygate CA, Johannsen M, Kharbanda RK, Neubauer S, Redwood C, de Cabo R, Ahmet I, Talan M, Günther UL, Robinson AJ, Viant MR, Pollard PJ, Tyler DJ, Watkins H (2012)Fumarate is cardioprotective via activation of the Nrf2 antioxidant pathway. Cell metabolism 15, Pubmed: 22405071
  • Jacobsen I, Hennig-Pauka I, Baltes N, Trost M, Gerlach GF (2005)Enzymes involved in anaerobic respiration appear to play a role in Actinobacillus pleuropneumoniae virulence. Infection and immunity 73, Pubmed: 15618158
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
CAS110-17-8
ChEBI29806
ChemSpider4573886
DrugBankDB01677
HMDBHMDB00134
IAF126033938
KEGGC00122
KNApSAcKC00001183
MetaboLightsMTBLC29806
PubChem5460307