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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:56:23 UTC
Update Date2022-03-07 03:17:43 UTC
HMDB IDHMDB0060361
Secondary Accession Numbers
  • HMDB60361
Metabolite Identification
Common Name2,3,5-Trichloromaleylacetate
Description2,3,5-Trichloromaleylacetate belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 2,3,5-Trichloromaleylacetate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,3,5-Trichloromaleylacetate exists in all living organisms, ranging from bacteria to humans. These are keto acids with a 6 to 12 carbon atoms long side chain.
Structure
Data?1563866049
Synonyms
ValueSource
2,3,5-Trichloromaleylacetic acidGenerator
2,3,5-TrichloromaleylacetateGenerator
Chemical FormulaC6H3Cl3O5
Average Molecular Weight261.444
Monoisotopic Molecular Weight259.904606327
IUPAC Name(2Z)-2,3,5-trichloro-4-oxohex-2-enedioic acid
Traditional NameC6H3cl3O5
CAS Registry NumberNot Available
SMILES
OC(=O)C(Cl)C(=O)C(\Cl)=C(\Cl)C(O)=O
InChI Identifier
InChI=1S/C6H3Cl3O5/c7-1(2(8)5(11)12)4(10)3(9)6(13)14/h3H,(H,11,12)(H,13,14)/b2-1-
InChI KeyADCWUQBAGPEBME-UPHRSURJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Beta-keto acid
  • Halogenated fatty acid
  • B'-hydroxy-alpha,beta-unsaturated-ketone
  • Beta-hydroxy ketone
  • Unsaturated fatty acid
  • 1,3-dicarbonyl compound
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alpha-halocarboxylic acid
  • Alpha,beta-unsaturated ketone
  • Alpha-chloroketone
  • Alpha-haloketone
  • Vinylogous halide
  • Enone
  • Acryloyl-group
  • Alpha-halocarboxylic acid or derivatives
  • Ketone
  • Carboxylic acid derivative
  • Vinyl chloride
  • Vinyl halide
  • Haloalkene
  • Chloroalkene
  • Carboxylic acid
  • Organic oxygen compound
  • Organohalogen compound
  • Carbonyl group
  • Organochloride
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alkyl halide
  • Alkyl chloride
  • 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 Solubility0.022 g/LALOGPS
logP1.72ALOGPS
logP1.6ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)1.68ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity48.47 m³·mol⁻¹ChemAxon
Polarizability19.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+148.2930932474
DeepCCS[M-H]-145.93230932474
DeepCCS[M-2H]-179.94730932474
DeepCCS[M+Na]+154.71130932474
AllCCS[M+H]+149.632859911
AllCCS[M+H-H2O]+146.232859911
AllCCS[M+NH4]+152.732859911
AllCCS[M+Na]+153.732859911
AllCCS[M-H]-142.632859911
AllCCS[M+Na-2H]-143.632859911
AllCCS[M+HCOO]-144.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,3,5-TrichloromaleylacetateOC(=O)C(Cl)C(=O)C(\Cl)=C(\Cl)C(O)=O2837.5Standard polar33892256
2,3,5-TrichloromaleylacetateOC(=O)C(Cl)C(=O)C(\Cl)=C(\Cl)C(O)=O1587.4Standard non polar33892256
2,3,5-TrichloromaleylacetateOC(=O)C(Cl)C(=O)C(\Cl)=C(\Cl)C(O)=O1896.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,3,5-Trichloromaleylacetate,1TMS,isomer #1C[Si](C)(C)OC(=O)C(Cl)C(=O)/C(Cl)=C(/Cl)C(=O)O1841.0Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,1TMS,isomer #2C[Si](C)(C)OC(=O)/C(Cl)=C(/Cl)C(=O)C(Cl)C(=O)O1802.2Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,1TMS,isomer #3C[Si](C)(C)OC(=C(Cl)C(=O)O)/C(Cl)=C(/Cl)C(=O)O1920.1Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,2TMS,isomer #1C[Si](C)(C)OC(=O)/C(Cl)=C(/Cl)C(=O)C(Cl)C(=O)O[Si](C)(C)C1868.3Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,2TMS,isomer #2C[Si](C)(C)OC(=O)C(Cl)=C(O[Si](C)(C)C)/C(Cl)=C(/Cl)C(=O)O1907.8Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,2TMS,isomer #3C[Si](C)(C)OC(=O)/C(Cl)=C(/Cl)C(O[Si](C)(C)C)=C(Cl)C(=O)O1895.9Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,3TMS,isomer #1C[Si](C)(C)OC(=O)C(Cl)=C(O[Si](C)(C)C)/C(Cl)=C(/Cl)C(=O)O[Si](C)(C)C1862.7Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,3TMS,isomer #1C[Si](C)(C)OC(=O)C(Cl)=C(O[Si](C)(C)C)/C(Cl)=C(/Cl)C(=O)O[Si](C)(C)C1844.1Standard non polar33892256
2,3,5-Trichloromaleylacetate,3TMS,isomer #1C[Si](C)(C)OC(=O)C(Cl)=C(O[Si](C)(C)C)/C(Cl)=C(/Cl)C(=O)O[Si](C)(C)C2063.6Standard polar33892256
2,3,5-Trichloromaleylacetate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(Cl)C(=O)/C(Cl)=C(/Cl)C(=O)O2084.0Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)/C(Cl)=C(/Cl)C(=O)C(Cl)C(=O)O2034.4Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=C(Cl)C(=O)O)/C(Cl)=C(/Cl)C(=O)O2167.1Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C(Cl)=C(/Cl)C(=O)C(Cl)C(=O)O[Si](C)(C)C(C)(C)C2329.1Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(Cl)=C(O[Si](C)(C)C(C)(C)C)/C(Cl)=C(/Cl)C(=O)O2374.1Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)/C(Cl)=C(/Cl)C(O[Si](C)(C)C(C)(C)C)=C(Cl)C(=O)O2368.0Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(Cl)=C(O[Si](C)(C)C(C)(C)C)/C(Cl)=C(/Cl)C(=O)O[Si](C)(C)C(C)(C)C2591.8Semi standard non polar33892256
2,3,5-Trichloromaleylacetate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(Cl)=C(O[Si](C)(C)C(C)(C)C)/C(Cl)=C(/Cl)C(=O)O[Si](C)(C)C(C)(C)C2464.3Standard non polar33892256
2,3,5-Trichloromaleylacetate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(Cl)=C(O[Si](C)(C)C(C)(C)C)/C(Cl)=C(/Cl)C(=O)O[Si](C)(C)C(C)(C)C2456.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,3,5-Trichloromaleylacetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ku-2930000000-64fbe07abac2e4eb86ae2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3,5-Trichloromaleylacetate GC-MS (2 TMS) - 70eV, Positivesplash10-00rl-9124000000-5c52c8a722bdf006d9e12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3,5-Trichloromaleylacetate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,3,5-Trichloromaleylacetate 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 - 2,3,5-Trichloromaleylacetate 10V, Positive-QTOFsplash10-03dl-1190000000-d03650aa455e2fd02f2a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,5-Trichloromaleylacetate 20V, Positive-QTOFsplash10-03di-0090000000-8de4d599b4d70f2eb0412017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,5-Trichloromaleylacetate 40V, Positive-QTOFsplash10-0006-9100000000-9584c99c08b848b3491b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,5-Trichloromaleylacetate 10V, Negative-QTOFsplash10-08g0-0590000000-531ea6d394d893ca85eb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,5-Trichloromaleylacetate 20V, Negative-QTOFsplash10-01ox-0390000000-9fb78f60140d1ed6bfcd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,3,5-Trichloromaleylacetate 40V, Negative-QTOFsplash10-00di-4920000000-9fc0a17364aa7a8199502017-10-06Wishart 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 IDC18243
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543107
PDB IDNot Available
ChEBI ID19297
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 hydrolase activity
Specific function:
Cysteine hydrolase. Can convert the prodrug olmesartan medoxomil into its pharmacologically active metabolite olmerstatan, an angiotensin receptor blocker, in liver and intestine. May also activate beta-lactam antibiotics faropenem medoxomil and lenampicillin.
Gene Name:
CMBL
Uniprot ID:
Q96DG6
Molecular weight:
Not Available
Reactions
2,3,5-Trichlorodienelactone + Water → 2,3,5-Trichloromaleylacetatedetails