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Cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide (M2MDB000976)

Record Information
Version2.0
Creation Date2012-05-31 14:28:58 -0600
Update Date2015-09-17 16:24:19 -0600
Secondary Accession Numbers
  • ECMDB20128
Identification
Name:Cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide
DescriptionCis-2-chloro-4-carboxymethylenebut-2-en-1,4-olide is a member of the chemical class known as Aryl Chlorides. These are organic compounds containing the acyl chloride functional group.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2E)-[4-chloro-5-oxofuran-2(5H)-ylidene]acetate
  • (2E)-[4-chloro-5-oxofuran-2(5H)-ylidene]acetic acid
  • (4-chloro-5-oxofuran-2(5H)-ylidene)acetate
  • (4-chloro-5-oxofuran-2(5H)-ylidene)acetic acid
  • 2-Chloro-4-carboxymethylenebut-2-en-1,4-olide
  • Cis-2-chloro-4-carboxymethylenebut-2-en-1,4-olide
  • Cis-2-Chlorodienelactone
Chemical Formula:C6H3ClO4
Weight:Average: 174.539
Monoisotopic: 173.971986291
InChI Key:ADSGHWJRPOXXTD-UHFFFAOYSA-N
InChI:InChI=1S/C6H3ClO4/c7-4-1-3(2-5(8)9)11-6(4)10/h1-2H,(H,8,9)
CAS number:115793-61-8
IUPAC Name:2-[(2E)-4-chloro-5-oxo-2,5-dihydrofuran-2-ylidene]acetic acid
Traditional IUPAC Name:cis-2-chlorodienelactone
SMILES:OC(=O)C=C1OC(=O)C(Cl)=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 derivative
  • Carboxylic acid
  • Oxacycle
  • Chloroalkene
  • Vinyl chloride
  • Vinyl halide
  • Haloalkene
  • Carbonyl group
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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 Solubility5.77 g/LALOGPS
logP1.05ALOGPS
logP0.57ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.68ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.12 m³·mol⁻¹ChemAxon
Polarizability14.13 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide + Water <> 2-Chloromaleylacetate
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, Positivesplash10-0a4i-0900000000-ec5e68f59e3f9cc4093dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-2900000000-43f8345fd63953bfd45bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9400000000-f76537ef830476b92a0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-0900000000-e330647823f39f504be9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fi0-0900000000-da063f538124339d8974View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-5900000000-89a661e0d3d8d0791ceaView 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 ID16211
HMDB IDNot Available
Pubchem Compound ID5280718
Kegg IDC04706
ChemSpider ID4444302
Wikipedia IDNot Available
BioCyc IDCIS-2-CHLORO-4-CARBOXYMETHYLENEBUT-2-EN-
EcoCyc IDCIS-2-CHLORO-4-CARBOXYMETHYLENEBUT-2-EN-

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.