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Cis-4-Carboxymethylenebut-2-en-4-olide (M2MDB000979)

Record Information
Version2.0
Creation Date2012-05-31 14:29:08 -0600
Update Date2015-06-03 17:19:22 -0600
Secondary Accession Numbers
  • ECMDB20131
Identification
Name:Cis-4-Carboxymethylenebut-2-en-4-olide
DescriptionCis-4-carboxymethylenebut-2-en-4-olide is a member of the chemical class known as Furans. These are compounds containing a furan ring, which is a five-member aromatic ring with one oxygen atom, four carbon atoms.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2Z)-(5-oxofuran-2(5H)-ylidene)acetate
  • (2Z)-(5-oxofuran-2(5H)-ylidene)acetic acid
  • (Z)-5-Oxodelta(2(5H),a)-furanacetate
  • (Z)-5-Oxodelta(2(5H),a)-furanacetic acid
  • (Z)-5-Oxodelta(2(5H),alpha)-furanacetate
  • (Z)-5-Oxodelta(2(5H),alpha)-furanacetic acid
  • (Z)-5-Oxodelta(2(5H),α)-furanacetate
  • (Z)-5-Oxodelta(2(5H),α)-furanacetic acid
  • 4-Carboxymethylenebut-2-en-4-olide
  • 5-oxo-(Z)-delta(2(5H),a)-Furanacetate
  • 5-oxo-(Z)-delta(2(5H),a)-Furanacetic acid
  • 5-Oxo-(Z)-delta(2(5H),alpha)-Furanacetate
  • 5-Oxo-(Z)-delta(2(5H),alpha)-Furanacetic acid
  • 5-oxo-(Z)-δ(2(5H),a)-Furanacetate
  • 5-oxo-(Z)-δ(2(5H),a)-Furanacetic acid
  • 5-oxo-(Z)-δ(2(5H),α)-Furanacetate
  • 5-oxo-(Z)-δ(2(5H),α)-Furanacetic acid
  • cis-4-carboxymethylenebut-2-en-4-olide
  • Dienelactone
  • Trans-4-Carboxymethylenebut-2-en-4-olide
Chemical Formula:C6H4O4
Weight:Average: 140.0936
Monoisotopic: 140.010958616
InChI Key:AYFXPGXAZMFWNH-ONEGZZNKSA-N
InChI:InChI=1S/C6H4O4/c7-5(8)3-4-1-2-6(9)10-4/h1-3H,(H,7,8)/b4-3+
CAS number:73237-79-3
IUPAC Name:2-[(2E)-5-oxo-2,5-dihydrofuran-2-ylidene]acetic acid
Traditional IUPAC Name:[(2E)-5-oxofuran-2-ylidene]acetic acid
SMILES:OC(=O)\C=C1\OC(=O)C=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Enol ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility23.1 g/LALOGPS
logP0.72ALOGPS
logP0.18ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.33 m³·mol⁻¹ChemAxon
Polarizability11.91 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Cis-4-Carboxymethylenebut-2-en-4-olide + Water <> 2-Maleylacetate
Cis-4-Carboxymethylenebut-2-en-4-olide + Water > 4-Oxohex-2-enedioate
SMPDB Pathways:
Fluorobenzoate degradationPW000766 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-9100000000-a9372b7bcb64119f38d0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9600000000-40562b3dbdce53cefdb4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-4da24f4d3150d4cb0d9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-285620f88db9e73b5eadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-9300000000-c40d20cf666aab67a491View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-5900000000-34a6a177544dbc512389View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0072-9600000000-42a684d27e1e540b3b12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f95-9000000000-ff8b053604593c0325bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9400000000-32ec3f966c201e73e6b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9100000000-acf0d7874c4fc167d1faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-f749d27c9aea80365dabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000b-9400000000-b7f9b56049121a6c58e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-bb74108b75d88d650746View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxu-9000000000-3ae3dd5a3949ebdd590fView 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:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18371
HMDB IDHMDB0060459
Pubchem Compound ID5280677
Kegg IDC04431
ChemSpider ID4444269
Wikipedia IDNot Available
BioCyc ID4-CARBOXYMETHYLENEBUT-2-EN-4-OLIDE
EcoCyc ID4-CARBOXYMETHYLENEBUT-2-EN-4-OLIDE

Enzymes

Protein Details
1. Putative carboxymethylenebutenolidase
General function:
Involved in hydrolase activity
Specific function:
4-carboxymethylenebut-2-en-4-olide + H(2)O = 4-oxohex-2-enedioate
Gene Name:
ysgA
Uniprot ID:
P56262
Molecular weight:
29425
Reactions
4-carboxymethylenebut-2-en-4-olide + H(2)O = 4-oxohex-2-enedioate.