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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:22:11 UTC
Update Date2023-02-21 17:30:00 UTC
HMDB IDHMDB0060457
Secondary Accession Numbers
  • HMDB60457
Metabolite Identification
Common Namecis-3-Chloroacrylic acid
Descriptioncis-3-Chloroacrylic acid belongs to the class of organic compounds known as acrylic acids and derivatives. These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof. These are compounds containing the enone functional group, with the structure RC(=O)CR'. cis-3-Chloroacrylic acid is a weakly acidic compound (based on its pKa). cis-3-Chloroacrylic acid exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1677000600
Synonyms
ValueSource
cis-3-ChloroacrylateGenerator
Chemical FormulaC3H3ClO2
Average Molecular Weight106.508
Monoisotopic Molecular Weight105.982157047
IUPAC Name(2Z)-3-chloroprop-2-enoic acid
Traditional Namecis-3-chloroacrylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)\C=C/Cl
InChI Identifier
InChI=1S/C3H3ClO2/c4-2-1-3(5)6/h1-2H,(H,5,6)/b2-1-
InChI KeyMHMUCYJKZUZMNJ-UPHRSURJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acrylic acids and derivatives. These are organic compounds containing acrylic acid CH2=CHCO2H or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAcrylic acids and derivatives
Direct ParentAcrylic acids and derivatives
Alternative Parents
Substituents
  • Acrylic acid or derivatives
  • Vinylogous halide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Vinyl chloride
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility68.4 g/LALOGPS
logP0.87ALOGPS
logP0.85ChemAxon
logS-0.19ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.09 m³·mol⁻¹ChemAxon
Polarizability8.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+119.49530932474
DeepCCS[M-H]-117.50630932474
DeepCCS[M-2H]-153.05330932474
DeepCCS[M+Na]+127.56530932474
AllCCS[M+H]+126.232859911
AllCCS[M+H-H2O]+121.932859911
AllCCS[M+NH4]+130.332859911
AllCCS[M+Na]+131.532859911
AllCCS[M-H]-128.732859911
AllCCS[M+Na-2H]-133.332859911
AllCCS[M+HCOO]-138.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-3-Chloroacrylic acidOC(=O)\C=C/Cl1948.7Standard polar33892256
cis-3-Chloroacrylic acidOC(=O)\C=C/Cl1060.8Standard non polar33892256
cis-3-Chloroacrylic acidOC(=O)\C=C/Cl1003.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
cis-3-Chloroacrylic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C\Cl1006.8Semi standard non polar33892256
cis-3-Chloroacrylic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C\Cl1228.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Chloroacrylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0btc-9100000000-bbf9d3f6573d087199cd2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Chloroacrylic acid GC-MS (1 TMS) - 70eV, Positivesplash10-022i-9300000000-d9c5912b0087dadc8a202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Chloroacrylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 10V, Positive-QTOFsplash10-000i-9200000000-dec804ffc79973ada8bc2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 20V, Positive-QTOFsplash10-000i-9200000000-05cb399c87d6b94ada202017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 40V, Positive-QTOFsplash10-03di-9000000000-3a28f9621c85ba799faa2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 10V, Negative-QTOFsplash10-0udi-4900000000-501026100c3ddf13b8c22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 20V, Negative-QTOFsplash10-0udr-9500000000-053e70b78bea60c18d0f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 40V, Negative-QTOFsplash10-014r-9000000000-bdf0a2d0391b14ffe92f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 10V, Positive-QTOFsplash10-000i-9100000000-f9070e77720772efd3aa2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 20V, Positive-QTOFsplash10-01p9-9000000000-f2b7c32dd259d19874e92021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 40V, Positive-QTOFsplash10-03di-9000000000-e03121d3ac56388b52822021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 10V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 20V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Chloroacrylic acid 40V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-10-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC06615
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound643794
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
cis-3-Chloroallyl aldehyde + Water → cis-3-Chloroacrylic acid + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
cis-3-Chloroallyl aldehyde + Water → cis-3-Chloroacrylic acid + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
cis-3-Chloroallyl aldehyde + Water → cis-3-Chloroacrylic acid + Hydrogen Iondetails