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cis-Acetylacrylate (M2MDB000980)

Record Information
Version2.0
Creation Date2012-05-31 14:29:11 -0600
Update Date2015-06-03 17:19:22 -0600
Secondary Accession Numbers
  • ECMDB20132
Identification
Name:cis-Acetylacrylate
DescriptionCis-acetylacrylate belongs to the class of Unsaturated Fatty Acids. These are fatty acids whose chain contains at least one CC double bond. (inferred from compound structure)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • Acetylacrylate
  • Acetylacrylic acid
  • Cis-Acetylacrylic acid
Chemical Formula:C5H6O3
Weight:Average: 114.0993
Monoisotopic: 114.031694058
InChI Key:XGTKSWVCNVUVHG-IHWYPQMZSA-N
InChI:InChI=1S/C5H6O3/c1-4(6)2-3-5(7)8/h2-3H,1H3,(H,7,8)/b3-2-
CAS number:Not Available
IUPAC Name:(2Z)-4-oxopent-2-enoic acid
Traditional IUPAC Name:cis-acetylacrylic acid
SMILES:[H]\C(=C(/[H])C(O)=O)C(C)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Short-chain keto acid
  • Fatty acyl
  • Unsaturated fatty acid
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility38.5 g/LALOGPS
logP0.31ALOGPS
logP0.29ChemAxon
logS-0.47ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity28.16 m³·mol⁻¹ChemAxon
Polarizability10.5 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Protoanemonin + Water <> cis-Acetylacrylate
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002g-9000000000-2061ae1a8861f42f1c73View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9400000000-f73d0beec9860c695eecView 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, Positivesplash10-0002-9100000000-853b506b94b09ffadf54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ftb-9000000000-12b21331ddede63beb81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-9000000000-e9848e2a1399185ca489View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-6900000000-f4fc97ecbaa587d81b1bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xs-9300000000-f9afeb3b5ff5e9af4bb8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fr2-9000000000-c0b2fd76e44f097e767bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014m-9000000000-1c4c26eebab1a2f95b1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fr6-9000000000-aa47fe3b96e724c2df4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-06ea02079a8a17b618dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9300000000-1628c355975cd34af232View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-818e5c336756d6610c5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9000000000-8840275d4a41857285d2View 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
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28993
HMDB IDHMDB0060461
Pubchem Compound ID5281015
Kegg IDC07091
ChemSpider ID4444490
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.