Fumaric Acid

Identification

Name
Fumaric Acid
Accession Number
DB01677  (EXPT01460, EXPT01511)
Type
Small Molecule
Groups
Experimental, Investigational
Description
Not 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
Categories
UNII
88XHZ13131
CAS number
110-17-8
Weight
Average: 116.0722
Monoisotopic: 116.010958616
Chemical Formula
C4H4O4
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+
IUPAC Name
(2E)-but-2-enedioic acid
SMILES
OC(=O)\C=C\C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMalate dehydrogenaseNot AvailableChloroflexus aurantiacus (strain ATCC 29366 / DSM 635 / J-10-fl)
UFumarate reductase flavoprotein subunitNot AvailableShewanella oneidensis (strain MR-1)
UNAD-dependent malic enzyme, mitochondrialNot AvailableHuman
UFumarylacetoacetaseNot AvailableHuman
UFumarate reductase flavoprotein subunitNot AvailableShewanella frigidimarina
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB00134
KEGG Drug
D02308
KEGG Compound
C00122
PubChem Compound
444972
PubChem Substance
46508303
ChemSpider
10197150
BindingDB
26122
ChEBI
18012
ChEMBL
CHEMBL503160
HET
FUM
RxList
RxList Drug Page
Wikipedia
Fumaric_Acid
ATC Codes
D05AX01 — Fumaric acid
PDB Entries
1d4e / 1e39 / 1gz3 / 1gz4 / 1jrx / 1jry / 1jrz / 1kss / 1ksu / 1lj1
show 37 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentPlaque Psoriasis1
3CompletedTreatmentPsoriasis1
Not AvailableCompletedNot AvailablePsoriasis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0002-2940000000-e988056514d4ce4acc27
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0002-2960000000-a5ebaf2bbade922838ec
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-0002-2950000000-32afa4d45e0e72b174b4
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-0950000000-fe0f05c02c783d0b6f6b
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)GC-MSsplash10-006t-9530000000-0fc03f31f09dc8dbf4c6
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0002-3690000000-75089756992cdbe841e3
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0002-9100000000-2cf649749b42cc0c610c
GC-MS Spectrum - EI-BGC-MSsplash10-0007-0890000000-b1c35cd55deb81254f66
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-2940000000-e988056514d4ce4acc27
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-2960000000-a5ebaf2bbade922838ec
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-2950000000-32afa4d45e0e72b174b4
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0950000000-fe0f05c02c783d0b6f6b
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-006t-9530000000-0fc03f31f09dc8dbf4c6
GC-MS Spectrum - GC-MSGC-MSsplash10-0002-3690000000-75089756992cdbe841e3
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0940000000-177fdb9168659029ffaa
Mass Spectrum (Electron Ionization)MSsplash10-0092-9000000000-003dd2d9303272b2ebea
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-00di-9100000000-57f13cd433a6fe4bf0b3
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-0229-9600000000-cd9e2979d0bb1e2a62f2
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-03k9-8900000000-dc50dbf8a50872383d54
MS/MS Spectrum - EI-B (HITACHI RMU-6L) , PositiveLC-MS/MSsplash10-0002-9100000000-b47e534bc82a6ed36e7c
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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 Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Dicarboxylic acids and derivatives
Direct Parent
Dicarboxylic acids and derivatives
Alternative Parents
Unsaturated fatty acids / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
butenedioic acid (CHEBI:18012)

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...
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...
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 November 09, 2017 03:03