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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:55:30 UTC
Update Date2023-02-21 17:29:53 UTC
HMDB IDHMDB0060348
Secondary Accession Numbers
  • HMDB60348
Metabolite Identification
Common Name2-Maleylacetate
Description2-Maleylacetate, also known as maleylacetic acid, 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-Maleylacetate is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1677000593
Synonyms
ValueSource
(Z)-4-oxo-2-Hexenedioic acidChEBI
4-Oxohex-2-enedioateChEBI
MaleylacetateChEBI
(Z)-4-oxo-2-HexenedioateGenerator
4-Oxohex-2-enedioic acidGenerator
Maleylacetic acidGenerator
2-Maleylacetic acidGenerator
Maleoylacetic acidMeSH
Chemical FormulaC6H6O5
Average Molecular Weight158.1088
Monoisotopic Molecular Weight158.021523302
IUPAC Name(2Z)-4-oxohex-2-enedioic acid
Traditional Namemaleylacetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CC(=O)\C=C/C(O)=O
InChI Identifier
InChI=1S/C6H6O5/c7-4(3-6(10)11)1-2-5(8)9/h1-2H,3H2,(H,8,9)(H,10,11)/b2-1-
InChI KeySOXXPQLIZIPMIZ-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
  • B'-hydroxy-alpha,beta-unsaturated-ketone
  • Fatty acyl
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • 1,3-dicarbonyl compound
  • Unsaturated fatty acid
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Enone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen 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 Solubility7.25 g/LALOGPS
logP-0.06ALOGPS
logP0.18ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)2.71ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.5 m³·mol⁻¹ChemAxon
Polarizability13.16 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]+129.44830932474
DeepCCS[M-H]-125.61830932474
DeepCCS[M-2H]-162.84330932474
DeepCCS[M+Na]+138.38330932474
AllCCS[M+H]+134.232859911
AllCCS[M+H-H2O]+130.132859911
AllCCS[M+NH4]+137.932859911
AllCCS[M+Na]+139.032859911
AllCCS[M-H]-128.532859911
AllCCS[M+Na-2H]-130.232859911
AllCCS[M+HCOO]-132.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-MaleylacetateOC(=O)CC(=O)\C=C/C(O)=O2725.0Standard polar33892256
2-MaleylacetateOC(=O)CC(=O)\C=C/C(O)=O1200.5Standard non polar33892256
2-MaleylacetateOC(=O)CC(=O)\C=C/C(O)=O1588.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Maleylacetate,1TMS,isomer #1C[Si](C)(C)OC(=O)CC(=O)/C=C\C(=O)O1585.1Semi standard non polar33892256
2-Maleylacetate,1TMS,isomer #2C[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)O1551.7Semi standard non polar33892256
2-Maleylacetate,1TMS,isomer #3C[Si](C)(C)OC(=CC(=O)O)/C=C\C(=O)O1750.3Semi standard non polar33892256
2-Maleylacetate,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)O[Si](C)(C)C1641.9Semi standard non polar33892256
2-Maleylacetate,2TMS,isomer #2C[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O)O[Si](C)(C)C1813.0Semi standard non polar33892256
2-Maleylacetate,2TMS,isomer #3C[Si](C)(C)OC(=O)/C=C\C(=CC(=O)O)O[Si](C)(C)C1809.0Semi standard non polar33892256
2-Maleylacetate,3TMS,isomer #1C[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C1821.5Semi standard non polar33892256
2-Maleylacetate,3TMS,isomer #1C[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C1741.0Standard non polar33892256
2-Maleylacetate,3TMS,isomer #1C[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C)O[Si](C)(C)C1792.3Standard polar33892256
2-Maleylacetate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CC(=O)/C=C\C(=O)O1820.8Semi standard non polar33892256
2-Maleylacetate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)O1786.9Semi standard non polar33892256
2-Maleylacetate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC(=O)O)/C=C\C(=O)O1980.6Semi standard non polar33892256
2-Maleylacetate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=O)CC(=O)O[Si](C)(C)C(C)(C)C2093.7Semi standard non polar33892256
2-Maleylacetate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O)O[Si](C)(C)C(C)(C)C2273.6Semi standard non polar33892256
2-Maleylacetate,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)/C=C\C(=CC(=O)O)O[Si](C)(C)C(C)(C)C2314.1Semi standard non polar33892256
2-Maleylacetate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2506.6Semi standard non polar33892256
2-Maleylacetate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2350.8Standard non polar33892256
2-Maleylacetate,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2148.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Maleylacetate GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9200000000-6cbb9b4c6c7936d0cff92016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Maleylacetate GC-MS (2 TMS) - 70eV, Positivesplash10-022i-9860000000-61befd7ba0403872d1ae2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Maleylacetate 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-Maleylacetate 10V, Negative-QTOFsplash10-0bti-3900000000-2025e2328c5b1fbdc64f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Maleylacetate 20V, Negative-QTOFsplash10-08fs-9600000000-ae443a75a844ee0bd1da2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Maleylacetate 40V, Negative-QTOFsplash10-066v-9100000000-1414fa6f2dc1874da3eb2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Maleylacetate 10V, Negative-QTOFsplash10-02t9-9600000000-c53bd6320b75c2dc69092021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Maleylacetate 20V, Negative-QTOFsplash10-014i-9100000000-36a3c561086be0ee94d32021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Maleylacetate 40V, Negative-QTOFsplash10-014i-9000000000-862eaff8183941aa3ff22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Maleylacetate 10V, Positive-QTOFsplash10-0006-1900000000-9f4bd73246c1ec182e882015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Maleylacetate 20V, Positive-QTOFsplash10-01vn-7900000000-eee90ce719bbc702b1c32015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Maleylacetate 40V, Positive-QTOFsplash10-006t-9100000000-9e9070ad596a90e7503f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Maleylacetate 10V, Positive-QTOFsplash10-0005-9600000000-9039551339c09bdfdca52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Maleylacetate 20V, Positive-QTOFsplash10-05mk-9000000000-1355e25670468c555e842021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Maleylacetate 40V, Positive-QTOFsplash10-00kf-9000000000-a445bad55c5cecfc7f5a2021-10-12Wishart 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 IDC00013593
Chemspider ID4444140
KEGG Compound IDC02222
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMaleylacetic acid
METLIN IDNot Available
PubChem Compound5280500
PDB IDNot Available
ChEBI ID1184
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
cis-4-Carboxymethylenebut-2-en-4-olide + Water → 2-Maleylacetatedetails
trans-4-Carboxymethylenebut-2-en-4-olide + Water → 2-Maleylacetatedetails
5-Fluoromuconolactone + Water → 2-Maleylacetate + Fluoridedetails
4-Fluoromuconolactone + Water → 2-Maleylacetate + Fluoridedetails