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Showing Compound fumarate (FDB030865)

Record Information
Version1.0
Creation date2015-05-07 20:19:52 UTC
Update date2020-09-17 15:38:22 UTC
Primary IDFDB030865
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namefumarate
DescriptionFumaric acid, also known as E297 or fumarsaeure, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Fumaric acid is a weakly acidic compound (based on its pKa). Fumaric acid exists in all living species, ranging from bacteria to humans. Within humans, fumaric acid participates in a number of enzymatic reactions. In particular, fumaric acid can be biosynthesized from L-malic acid; which is catalyzed by the enzyme fumarate hydratase, mitochondrial. In addition, fumaric acid can be biosynthesized from succinic acid through the action of the enzyme mutant succinate dehydrogenase. A butenedioic acid in which the C=C double bond has E geometry. In humans, fumaric acid is involved in the metabolic disorder called the glutaminolysis and cancer pathway. Fumaric acid is an odorless and sour tasting compound. Outside of the human body, Fumaric acid is found, on average, in the highest concentration within a few different foods, such as sweet cherries, star fruits, and milk (cow) and in a lower concentration in grape wines. Fumaric acid has also been detected, but not quantified in, several different foods, such as cow milks, apples, fishes, garden rhubarbs, and common sages. This could make fumaric acid a potential biomarker for the consumption of these foods. Fumaric acid is a potentially toxic compound. Fumaric acid, with regard to humans, has been found to be associated with several diseases such as rheumatoid arthritis, eosinophilic esophagitis, and lung cancer; fumaric acid has also been linked to several inborn metabolic disorders including 2-ketoglutarate dehydrogenase complex deficiency and fumarase deficiency.
CAS Number110-17-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(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
trans-2-ButenedioateHMDB
trans-2-Butenedioic acidHMDB
FuramagHMDB
MafusolHMDB
Fumaric acidHMDB
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H4O4
IUPAC name(2E)-but-2-enedioic acid
InChI IdentifierInChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
InChI KeyVZCYOOQTPOCHFL-OWOJBTEDSA-N
Isomeric SMILESOC(=O)\C=C\C(O)=O
Average Molecular Weight116.0722
Monoisotopic Molecular Weight116.010958616
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 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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Environmental role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0092-9000000000-003dd2d9303272b2ebeaSpectrum
GC-MSfumarate, 2 TMS, GC-MS Spectrumsplash10-0002-2940000000-e988056514d4ce4acc27Spectrum
GC-MSfumarate, 2 TMS, GC-MS Spectrumsplash10-0002-2960000000-a5ebaf2bbade922838ecSpectrum
GC-MSfumarate, 2 TMS, GC-MS Spectrumsplash10-0002-2950000000-32afa4d45e0e72b174b4Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-0950000000-fe0f05c02c783d0b6f6bSpectrum
GC-MSfumarate, 2 TMS, GC-MS Spectrumsplash10-006t-9530000000-0fc03f31f09dc8dbf4c6Spectrum
GC-MSfumarate, 2 TMS, GC-MS Spectrumsplash10-0002-3690000000-75089756992cdbe841e3Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-9100000000-2cf649749b42cc0c610cSpectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0007-0890000000-b1c35cd55deb81254f66Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-2940000000-e988056514d4ce4acc27Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-2960000000-a5ebaf2bbade922838ecSpectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-2950000000-32afa4d45e0e72b174b4Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-0950000000-fe0f05c02c783d0b6f6bSpectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-006t-9530000000-0fc03f31f09dc8dbf4c6Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-3690000000-75089756992cdbe841e3Spectrum
GC-MSfumarate, non-derivatized, GC-MS Spectrumsplash10-0002-0940000000-177fdb9168659029ffaaSpectrum
Predicted GC-MSfumarate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ba-9200000000-52f88e04bac0ff8cdf17Spectrum
Predicted GC-MSfumarate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8920000000-06da44f348d0fe0358b3Spectrum
Predicted GC-MSfumarate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSfumarate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSfumarate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSfumarate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSfumarate, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-00di-9100000000-57f13cd433a6fe4bf0b3Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0229-9600000000-cd9e2979d0bb1e2a62f2Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-03k9-8900000000-dc50dbf8a50872383d54Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0002-9100000000-b47e534bc82a6ed36e7cSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-04b277f233e1bd56c9afSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-4900000000-99764eff7d7cb7bfaee3Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-9000000000-453b921a0aaf64cfd558Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9000000000-cd7e7026d13bb5fe844bSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00dj-9000000000-383c22a29e2769626c47Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ir3-9000000000-3013847e2e0f9bf18d29Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00di-9000000000-9cc4f29b523ed34dc0b6Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-00di-9000000000-d9885a6093f38dd8b9faSpectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-00di-9000000000-46fdee94b5a787f1b81fSpectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03k9-8900000000-3ff0fb725ec9dffc3688Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014m-9000000000-394fd8f1b59c7befec9dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9800000000-dbf34563376daeb2901fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-9200000000-113bf08cdc77707ed3adSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9000000000-f32d7ec65e8649bc2b0aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-408d53a9fff7acc8ca23Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6900000000-f149e9e5a34e27dd4d4eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxt-9000000000-cae5f71dc27daaf17d9eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-3d34cd791255c022876aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-55a5c43ec34fdd2cb0a4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-9000000000-7c9639a65d534cd8ff97Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-9000000000-c5eb63dc643f72e91edeSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference