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Identification
YMDB IDYMDB00159
Namecis-4-carboxymethylenebut-2-en-4-olide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptioncis-4-Carboxymethylenebut-2-en-4-olide, also known as (5-oxo-2(5H)-furanylidene)acetic acid, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. cis-4-Carboxymethylenebut-2-en-4-olide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • (5-oxo-2(5H)-furanylidene)acetic acid
  • 4-Carboxymethylenebut-2-en-4-olide
  • cis-4-Carboxymethylenebut-2-en-4-olide
  • (5-oxo-2(5H)-Furanylidene)acetate
  • Dienelactone
  • cis-Dienelactone
CAS number73237-79-3
WeightAverage: 140.0936
Monoisotopic: 140.010958616
InChI KeyAYFXPGXAZMFWNH-ONEGZZNKSA-N
InChIInChI=1S/C6H4O4/c7-5(8)3-4-1-2-6(9)10-4/h1-3H,(H,7,8)/b4-3+
IUPAC Name2-[(2E)-5-oxo-2,5-dihydrofuran-2-ylidene]acetic acid
Traditional IUPAC Name[(2E)-5-oxofuran-2-ylidene]acetic acid
Chemical FormulaC6H4O4
SMILESOC(=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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fb9-9100000000-a9372b7bcb64119f38d0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9600000000-40562b3dbdce53cefdb4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-4da24f4d3150d4cb0d9cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-285620f88db9e73b5eadJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-9300000000-c40d20cf666aab67a491JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-5900000000-34a6a177544dbc512389JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0072-9600000000-42a684d27e1e540b3b12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f95-9000000000-ff8b053604593c0325bbJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18371
HMDB IDHMDB0060459
Pubchem Compound ID5459914
Kegg IDC04431
ChemSpider ID4573642
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in hydrolase activity
Specific function:
4-carboxymethylenebut-2-en-4-olide + H(2)O = 4-oxohex-2-enedioate
Gene Name:
Not Available
Uniprot ID:
Q07505
Molecular weight:
30836.90039
Reactions
4-carboxymethylenebut-2-en-4-olide + H(2)O → 4-oxohex-2-enedioate.