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Record Information
Version2.0
Creation Date2012-10-10 12:13:24 -0600
Update Date2015-06-03 17:25:46 -0600
Secondary Accession Numbers
  • ECMDB23032
Identification
Name:(E)-3-(Methoxycarbonyl)pent-2-enedioate
Description(E)-3-(Methoxycarbonyl)pent-2-enedioate is an intermediate in the synthesis of S-adenosyl-homocysteine. It is a substrate for the enzyme trans-aconitate 2-methyltransferase which catalyzes the following reaction: S-adenosyl-L-methionine + trans-aconitate = S-adenosyl-L-homocysteine + (E)-3-(methoxycarbonyl)pent-2-enedioate.
Structure
Thumb
Synonyms:
  • (2E)-3-(Methoxycarbonyl)-2-pentenedioate
  • (2E)-3-(Methoxycarbonyl)-2-pentenedioic acid
  • (e)-3-(Methoxycarbonyl)pent-2-enedioic acid
  • (e)-3-Methoxycarbonylpent-2-enedioate
  • (E)-3-methoxycarbonylpent-2-enedioic acid
Chemical Formula:C7H8O6
Weight:Average: 188.1348
Monoisotopic: 188.032087988
InChI Key:BRYKYSQCLNCYQW-DUXPYHPUSA-N
InChI:InChI=1S/C7H8O6/c1-13-7(12)4(2-5(8)9)3-6(10)11/h2H,3H2,1H3,(H,8,9)(H,10,11)/b4-2+
CAS number:Not Available
IUPAC Name:(2E)-3-(methoxycarbonyl)pent-2-enedioic acid
Traditional IUPAC Name:(2E)-3-(methoxycarbonyl)pent-2-enedioic acid
SMILES:COC(=O)C(\CC(O)=O)=C\C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility6.22 g/LALOGPS
logP-0.04ALOGPS
logP-0.14ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.01ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability16.31 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-2900000000-6379a9531abf5e2ab4b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-de792f927b6e9e3b9bb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00g0-1900000000-9c4d95ca18961b07eaddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ri-7900000000-78bb4fdb09c87da27492View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-8064594bd2f528217e46View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-1900000000-efd95865affda1bd0755View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-4fe14a0cdcb30b11abd1View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15663
HMDB IDNot Available
Pubchem Compound ID5281931
Kegg IDC11514
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in trans-aconitate 2-methyltransferase activity
Specific function:
Catalyzes the S-adenosylmethionine monomethyl esterification of trans-aconitate at high affinity and of cis- aconitate, isocitrate, and citrate at lower velocities and affinities
Gene Name:
tam
Uniprot ID:
P76145
Molecular weight:
29006
Reactions
S-adenosyl-L-methionine + trans-aconitate = S-adenosyl-L-homocysteine + (E)-3-(methoxycarbonyl)pent-2-enedioate.