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Showing Compound fumarate (FDB030865)

Record Information
Version1.0
Creation date2015-05-07 20:19:52 UTC
Update date2024-11-29 22:26:49 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
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
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0092-9000000000-003dd2d9303272b2ebea2014-09-20View Spectrum
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-9100000000-57f13cd433a6fe4bf0b32012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0229-9600000000-cd9e2979d0bb1e2a62f22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-03k9-8900000000-dc50dbf8a50872383d542012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0002-9100000000-b47e534bc82a6ed36e7c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-04b277f233e1bd56c9af2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03di-4900000000-99764eff7d7cb7bfaee32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-9000000000-453b921a0aaf64cfd5582021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9000000000-cd7e7026d13bb5fe844b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00dj-9000000000-383c22a29e2769626c472021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0ir3-9000000000-3013847e2e0f9bf18d292021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00di-9000000000-9cc4f29b523ed34dc0b62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-00di-9000000000-d9885a6093f38dd8b9fa2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-00di-9000000000-46fdee94b5a787f1b81f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03k9-8900000000-3ff0fb725ec9dffc36882021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-014m-9000000000-394fd8f1b59c7befec9d2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9800000000-dbf34563376daeb2901f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-9200000000-113bf08cdc77707ed3ad2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9000000000-f32d7ec65e8649bc2b0a2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-408d53a9fff7acc8ca232016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-6900000000-f149e9e5a34e27dd4d4e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fxt-9000000000-cae5f71dc27daaf17d9e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-3d34cd791255c022876a2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-55a5c43ec34fdd2cb0a42021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uk9-9000000000-7c9639a65d534cd8ff972021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-9000000000-c5eb63dc643f72e91ede2021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference