Trans-4-Carboxymethylenebut-2-en-4-olide (ECMDB20198) (M2MDB001044)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (319)
Record Information
Version2.0
Creation Date2012-05-31 14:32:42 -0600
Update Date2015-09-17 16:24:22 -0600
Secondary Accession Numbers
  • ECMDB20198
Identification
Name:Trans-4-Carboxymethylenebut-2-en-4-olide
DescriptionTrans-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
Chemical Formula:C6H4O4
Weight:Average: 140.0936
Monoisotopic: 140.010958616
InChI Key:AYFXPGXAZMFWNH-UHFFFAOYSA-N
InChI:InChI=1S/C6H4O4/c7-5(8)3-4-1-2-6(9)10-4/h1-3H,(H,7,8)
CAS number:22752-92-7
IUPAC Name:2-[(2Z)-5-oxo-2,5-dihydrofuran-2-ylidene]acetic acid
Traditional IUPAC Name:[(2Z)-5-oxofuran-2-ylidene]acetic acid
SMILES:OC(=O)C=C1OC(=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
Polarizability11.76 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Trans-4-Carboxymethylenebut-2-en-4-olide + Water <> 2-Maleylacetate
SMPDB Pathways:Not Available
KEGG Pathways:
  • Microbial metabolism in diverse environments ec01120
  • gamma-Hexachlorocyclohexane degradation ec00361
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-4aa5a329057a3bb6af5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-5900000000-59263817cf641a396d90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f92-9100000000-d653bf6a7707fdfd1760View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-5900000000-7b5c7c4cf6a5d0df1515View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0072-9600000000-be875c2c6f1606e6a493View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6w-9000000000-2a7c05d45dbb2afcfde9View in MoNA
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 ID38107
HMDB IDNot Available
Pubchem Compound ID5280677
Kegg IDC12838
ChemSpider ID4444269
Wikipedia IDNot Available
BioCyc IDNot Available

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.