(2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid (YMDB00122)

Identification

YMDB ID

YMDB00122

Name

(2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid

Species

Saccharomyces cerevisiae

Strain

Baker'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

MOL SDF PDB SMILES InChI

Synonyms

(2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid
(E)-2-(Methoxycarbonylmethyl)butenedioate
(e)-2-(Methoxycarbonylmethyl)butenedioic acid
(2E)-2-(Methoxycarbonylmethyl)but-2-enedioate

CAS number

Not Available

Weight

Average: 188.1348
Monoisotopic: 188.032087988

InChI Key

MRNZYUAGJLJQAM-DUXPYHPUSA-N

InChI

InChI=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 Formula

C₇H₈O₆

SMILES

COC(=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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:15661 )
methyl ester (CHEBI:15661 )

Physical Properties

State

Not Available

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	6.22 g/L	ALOGPS
logP	-0.02	ALOGPS
logP	-0.38	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.51	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40 m³·mol⁻¹	ChemAxon
Polarizability	16.28 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-4900000000-2037808c2faf5267c9a3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-059i-0900000000-b9b8172675fbf50735a4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-2900000000-78b5436c5203bf88bc63	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dj-6900000000-6e260e5c08d47dbaed5f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000l-0900000000-444fd352ebbd5fd620c5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01p6-1900000000-72f360f225bbf5c8b364	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9400000000-7c596ebd699a393d4851	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	15661
HMDB ID	Not Available
Pubchem Compound ID	5281932
Kegg ID	C11515
ChemSpider ID	25057185
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Trans-aconitate 3-methyltransferase

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.

(2E)-2-(methoxycarbonylmethyl)but-2-enedioic acid (YMDB00122)

Structure for #<Compound:0xa3aad20c>

Enzymes

Reactions