Identification
NameFumaric Acid
Accession NumberDB01677  (EXPT01460, EXPT01511)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
(2E)-2-butenedioic acid
(E)-2-butenedioic acid
Fumaricum acidum
Fumarsäure
trans-1,2-ethylenedicarboxylic acid
trans-but-2-enedioic acid
trans-Butenedioic acid
External IDs E-297 / FEMA NO. 2488 / INS NO.297 / INS-297 / NSC-2752
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII88XHZ13131
CAS number110-17-8
WeightAverage: 116.0722
Monoisotopic: 116.010958616
Chemical FormulaC4H4O4
InChI KeyVZCYOOQTPOCHFL-OWOJBTEDSA-N
InChI
InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
IUPAC Name
(2E)-but-2-enedioic acid
SMILES
OC(=O)\C=C\C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Malate dehydrogenaseProteinunknownNot AvailableChloroflexus aurantiacus (strain ATCC 29366 / DSM 635 / J-10-fl)P80040 details
Fumarate reductase flavoprotein subunitProteinunknownNot AvailableShewanella oneidensis (strain MR-1)P83223 details
NAD-dependent malic enzyme, mitochondrialProteinunknownNot AvailableHumanP23368 details
FumarylacetoacetaseProteinunknownNot AvailableHumanP16930 details
Fumarate reductase flavoprotein subunitProteinunknownNot AvailableShewanella frigidimarinaP0C278 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis Reference

Chung Kun Shih, Craig W. Gleason, Edmund H. Braun, II, "Solventless process for producing dialkyl fumarate-vinyl acetate copolymers." U.S. Patent US4772674, issued September, 1980.

US4772674
General ReferencesNot Available
External Links
ATC CodesD05AX01 — Fumaric acid
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentPlaque Psoriasis1
Not AvailableCompletedNot AvailablePsoriasis1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)287 dec °CPhysProp
boiling point (°C)522 °CPhysProp
water solubility7000 mg/L (at 25 °C)US EPA (1981)
logP0.46HANSCH,C ET AL. (1995)
pKa3.03 (at 18 °C)LIDE,DR (1996)
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7887
Blood Brain Barrier+0.9647
Caco-2 permeable-0.5173
P-glycoprotein substrateNon-substrate0.8606
P-glycoprotein inhibitor INon-inhibitor0.981
P-glycoprotein inhibitor IINon-inhibitor0.9857
Renal organic cation transporterNon-inhibitor0.9554
CYP450 2C9 substrateNon-substrate0.8341
CYP450 2D6 substrateNon-substrate0.9298
CYP450 3A4 substrateNon-substrate0.7844
CYP450 1A2 substrateNon-inhibitor0.9137
CYP450 2C9 inhibitorNon-inhibitor0.9264
CYP450 2D6 inhibitorNon-inhibitor0.9486
CYP450 2C19 inhibitorNon-inhibitor0.9485
CYP450 3A4 inhibitorNon-inhibitor0.9524
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.977
Ames testNon AMES toxic0.7926
CarcinogenicityNon-carcinogens0.5114
BiodegradationReady biodegradable0.9713
Rat acute toxicity2.1231 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9714
hERG inhibition (predictor II)Non-inhibitor0.9929
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
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
GC-MSGC-MS Spectrum - EI-Bsplash10-0002-9100000000-2cf649749b42cc0c610cView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0007-0890000000-b1c35cd55deb81254f66View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0940000000-177fdb9168659029ffaaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0940000000-177fdb9168659029ffaaView 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, 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
Taxonomy
ClassificationNot classified

Targets

Kind
Protein
Organism
Chloroflexus aurantiacus (strain ATCC 29366 / DSM 635 / J-10-fl)
Pharmacological action
unknown
General Function:
L-malate dehydrogenase activity
Specific Function:
Catalyzes the reversible oxidation of malate to oxaloacetate.
Gene Name:
mdh
Uniprot ID:
P80040
Uniprot Name:
Malate dehydrogenase
Molecular Weight:
32750.54 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Shewanella oneidensis (strain MR-1)
Pharmacological action
unknown
General Function:
Succinate dehydrogenase activity
Specific Function:
Catalyzes fumarate reduction using artificial electron donors such as methyl viologen. The physiological reductant is unknown, but evidence indicates that flavocytochrome c participates in electron transfer from formate to fumarate and possibly also to trimethylamine oxide (TMAO). This enzyme is essentially unidirectional (By similarity).
Gene Name:
Not Available
Uniprot ID:
P83223
Uniprot Name:
Fumarate reductase flavoprotein subunit
Molecular Weight:
62447.475 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Oxaloacetate decarboxylase activity
Specific Function:
Not Available
Gene Name:
ME2
Uniprot ID:
P23368
Uniprot Name:
NAD-dependent malic enzyme, mitochondrial
Molecular Weight:
65442.945 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Not Available
Gene Name:
FAH
Uniprot ID:
P16930
Uniprot Name:
Fumarylacetoacetase
Molecular Weight:
46373.97 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Shewanella frigidimarina
Pharmacological action
unknown
General Function:
Succinate dehydrogenase activity
Specific Function:
Catalyzes fumarate reduction using artificial electron donors such as methyl viologen. The physiological reductant is unknown, but evidence indicates that flavocytochrome c participates in electron transfer from formate to fumarate and possibly also to trimethylamine oxide (TMAO). This enzyme is essentially unidirectional.
Gene Name:
fccA
Uniprot ID:
P0C278
Uniprot Name:
Fumarate reductase flavoprotein subunit
Molecular Weight:
60620.95 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 17:01