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Identification
NameFumarate
Accession NumberDB01677  (EXPT01460, EXPT01511)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers 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
SaltsNot Available
CategoriesNot Available
UNII88XHZ13131
CAS number110-17-8
WeightAverage: 114.0563
Monoisotopic: 113.995308552
Chemical FormulaC4H2O4
InChI KeyInChIKey=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+
IUPAC Name
(2E)-but-2-enedioate
SMILES
[O-]C(=O)\C=C\C([O-])=O
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.
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 salt
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point287 dec °CPhysProp
boiling point522 °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 Solubility206.0 mg/mLALOGPS
logP-0.02ALOGPS
logP-0.041ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area80.26 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.28 m3·mol-1ChemAxon
Polarizability8.65 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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
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
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
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
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23