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Record Information

Version

2.0

Creation Date

2012-10-10 12:13:24 -0600

Update Date

2015-06-03 17:25:46 -0600

Secondary Accession Numbers

ECMDB23032

Identification

Name:

(E)-3-(Methoxycarbonyl)pent-2-enedioate

Description

(E)-3-(Methoxycarbonyl)pent-2-enedioate is an intermediate in the synthesis of S-adenosyl-homocysteine. It is a substrate for the enzyme trans-aconitate 2-methyltransferase which catalyzes the following reaction: S-adenosyl-L-methionine + trans-aconitate = S-adenosyl-L-homocysteine + (E)-3-(methoxycarbonyl)pent-2-enedioate.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

(2E)-3-(Methoxycarbonyl)-2-pentenedioate
(2E)-3-(Methoxycarbonyl)-2-pentenedioic acid
(e)-3-(Methoxycarbonyl)pent-2-enedioic acid
(e)-3-Methoxycarbonylpent-2-enedioate
(E)-3-methoxycarbonylpent-2-enedioic acid

Chemical Formula:

C₇H₈O₆

Weight:

Average: 188.1348
Monoisotopic: 188.032087988

InChI Key:

BRYKYSQCLNCYQW-DUXPYHPUSA-N

InChI:

InChI=1S/C7H8O6/c1-13-7(12)4(2-5(8)9)3-6(10)11/h2H,3H2,1H3,(H,8,9)(H,10,11)/b4-2+

CAS number:

Not Available

IUPAC Name:

(2E)-3-(methoxycarbonyl)pent-2-enedioic acid

Traditional IUPAC Name:

(2E)-3-(methoxycarbonyl)pent-2-enedioic acid

SMILES:

COC(=O)C(\CC(O)=O)=C\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 ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
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:15663 )
methyl ester (CHEBI:15663 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	6.22 g/L	ALOGPS
logP	-0.04	ALOGPS
logP	-0.14	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.01	ChemAxon
pKa (Strongest Basic)	-6.9	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	16.31 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

Reactions:

S-adenosyl-L-methionine + trans-Aconitic acid > S-Adenosylhomocysteine + (E)-3-(Methoxycarbonyl)pent-2-enedioate

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-2900000000-6379a9531abf5e2ab4b2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-de792f927b6e9e3b9bb0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00g0-1900000000-9c4d95ca18961b07eadd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ri-7900000000-78bb4fdb09c87da27492	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-8064594bd2f528217e46	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-1900000000-efd95865affda1bd0755	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9200000000-4fe14a0cdcb30b11abd1	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15663
HMDB ID	Not Available
Pubchem Compound ID	5281931
Kegg ID	C11514
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Trans-aconitate 2-methyltransferase

General function:: Involved in trans-aconitate 2-methyltransferase activity
Specific function:: Catalyzes the S-adenosylmethionine monomethyl esterification of trans-aconitate at high affinity and of cis- aconitate, isocitrate, and citrate at lower velocities and affinities
Gene Name:: tam
Uniprot ID:: P76145
Molecular weight:: 29006

Reactions

S-adenosyl-L-methionine + trans-aconitate = S-adenosyl-L-homocysteine + (E)-3-(methoxycarbonyl)pent-2-enedioate.

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(E)-3-(Methoxycarbonyl)pent-2-enedioate (M2MDB003422)

Structure for #<Compound:0x6e6c3324>

Enzymes

Reactions