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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 00:55:30 UTC
Update Date2019-07-23 07:14:08 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). A 2-Maleylacetate with a Z-configuration.
Structure
Data?1563866048
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
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9200000000-6cbb9b4c6c7936d0cff9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-022i-9860000000-61befd7ba0403872d1aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-9f4bd73246c1ec182e88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vn-7900000000-eee90ce719bbc702b1c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9100000000-9e9070ad596a90e7503fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bti-3900000000-2025e2328c5b1fbdc64fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fs-9600000000-ae443a75a844ee0bd1daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-066v-9100000000-1414fa6f2dc1874da3ebSpectrum
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 ID
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