You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-17 01:26:38 UTC
Update Date2019-07-23 07:14:30 UTC
HMDB IDHMDB0060518
Secondary Accession Numbers
  • HMDB60518
Metabolite Identification
Common Nametrans-4-Carboxymethylenebut-2-en-4-olide
DescriptionThis compound belongs to the family of Butenolides. These are dihydrofurans with a carbonyk group at the C2 carbon atom.
Structure
Data?1563866070
SynonymsNot Available
Chemical FormulaC6H4O4
Average Molecular Weight140.0936
Monoisotopic Molecular Weight140.010958616
IUPAC Name2-(5-oxo-2,5-dihydrofuran-2-ylidene)acetic acid
Traditional Name(5-oxofuran-2-ylidene)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C=C1OC(=O)C=C1
InChI Identifier
InChI=1S/C6H4O4/c7-5(8)3-4-1-2-6(9)10-4/h1-3H,(H,7,8)
InChI KeyAYFXPGXAZMFWNH-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Dicarboxylic acid or derivatives
  • Enol ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Lactone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 Solubility23.1 g/LALOGPS
logP0.72ALOGPS
logP0.18ChemAxon
logS-0.78ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.33 m³·mol⁻¹ChemAxon
Polarizability11.76 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-9100000000-212490d563858022fe2fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9600000000-40562b3dbdce53cefdb4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-4da24f4d3150d4cb0d9cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-285620f88db9e73b5eadJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-9300000000-c40d20cf666aab67a491JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-5900000000-34a6a177544dbc512389JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0072-9600000000-42a684d27e1e540b3b12JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f95-9000000000-ff8b053604593c0325bbJSpectraViewer | MoNA
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound120
PDB IDNot Available
ChEBI ID11972
Food Biomarker OntologyNot Available
VMH 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
trans-4-Carboxymethylenebut-2-en-4-olide + Water → 2-Maleylacetatedetails