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Identification
YMDB IDYMDB00122
Name(2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups (2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
Synonyms
  • (2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid
  • (E)-2-(Methoxycarbonylmethyl)butenedioate
  • (e)-2-(Methoxycarbonylmethyl)butenedioic acid
  • (2E)-2-(Methoxycarbonylmethyl)but-2-enedioate
CAS numberNot Available
WeightAverage: 188.1348
Monoisotopic: 188.032087988
InChI KeyMRNZYUAGJLJQAM-DUXPYHPUSA-N
InChIInChI=1S/C7H8O6/c1-13-6(10)3-4(7(11)12)2-5(8)9/h2H,3H2,1H3,(H,8,9)(H,11,12)/b4-2+
IUPAC Name(2E)-2-(2-methoxy-2-oxoethyl)but-2-enedioic acid
Traditional IUPAC Name(2E)-2-(2-methoxy-2-oxoethyl)but-2-enedioic acid
Chemical FormulaC7H8O6
SMILESCOC(=O)C\C(=C/C(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Fatty acid methyl ester
  • Fatty acid ester
  • Fatty acyl
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.22 g/LALOGPS
logP-0.02ALOGPS
logP-0.38ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.51ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40 m³·mol⁻¹ChemAxon
Polarizability16.28 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-4900000000-2037808c2faf5267c9a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059i-0900000000-b9b8172675fbf50735a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-78b5436c5203bf88bc63JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dj-6900000000-6e260e5c08d47dbaed5fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-0900000000-444fd352ebbd5fd620c5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01p6-1900000000-72f360f225bbf5c8b364JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9400000000-7c596ebd699a393d4851JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15661
HMDB IDNot Available
Pubchem Compound ID5281932
Kegg IDC11515
ChemSpider ID25057185
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in methyltransferase activity
Specific function:
Catalyzes the S-adenosylmethionine monomethyl esterification of trans-aconitate and 3-isopropylmalate at high affinity and of other molecules like cis-aconitate, isocitrate, and citrate at lower velocities and affinities. The function of trans-aconitate methylation appears to be in reducing the toxicity of this spontaneous breakdown product of cis-aconitate. The role of 3-isopropylmalate methylation is unclear but may represent a metabolic branch at 3-isopropylmalate, where some of the material is taken in the pathway leading to leucine and some is taken in a pathway to the 3-isopropylmalate methyl ester, a molecule that provides a signal to switch from vegetative to invasive growth in response to amino acid starvation
Gene Name:
TMT1
Uniprot ID:
P32643
Molecular weight:
34768.0
Reactions
S-adenosyl-L-methionine + trans-aconitate → S-adenosyl-L-homocysteine + (E)-2-(methoxycarbonylmethyl)butenedioate.