MiMeDB: Showing metabocard for (E)-3-(Methoxycarbonyl)pent-2-enedioate (MMDBc0031735)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:47:03 UTC

Update Date

2022-08-31 18:24:02 UTC

Metabolite ID

MMDBc0031735

Metabolite Identification

Common 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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      10.857  -6.489   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.188  -7.263   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.520  -6.489   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.520  -4.972   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.898  -4.262   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.857  -4.972   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.526  -7.263   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      14.874  -2.832   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      16.276  -4.989   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.851  -7.263   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      14.851  -8.811   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      16.182  -6.489   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      17.545  -7.263   0.000  0.00  0.00           C+0
CONECT    1    2    7    6                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    9    8                                                  
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    3   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
(e)-3-(Methoxycarbonyl)pent-2-enedioic acid	Generator
(e)-3-(Methoxycarbonyl)pent-2-enedioate	ChEBI
(2E)-3-(Methoxycarbonyl)pent-2-enedioate	Generator

Molecular Formula

C₇H₈O₆

Average Mass

188.1348

Monoisotopic Mass

188.032087988

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC(=O)C(\CC(O)=O)=C\C(O)=O

InChI Identifier

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+

InChI Key

BRYKYSQCLNCYQW-DUXPYHPUSA-N

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-2900000000-6379a9531abf5e2ab4b2	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-de792f927b6e9e3b9bb0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00g0-1900000000-9c4d95ca18961b07eadd	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ri-7900000000-78bb4fdb09c87da27492	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-8064594bd2f528217e46	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-1900000000-efd95865affda1bd0755	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9200000000-4fe14a0cdcb30b11abd1	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	72	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Sheep ; Pig	Unknown
Bacteria	Deinococcus-thermus	1
Bacteria	Actinobacteria	17	Human ; Cattle
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C11514

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281931

PDB ID

Not Available

ChEBI ID

15663

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (E)-3-(Methoxycarbonyl)pent-2-enedioate (MMDBc0031735)

MOL for #<Metabolite:0x00007fdb51e28158>

3D MOL for #<Metabolite:0x00007fdb51e28158>

3D SDF for #<Metabolite:0x00007fdb51e28158>

3D-SDF for #<Metabolite:0x00007fdb51e28158>

PDB for #<Metabolite:0x00007fdb51e28158>

3D PDB for #<Metabolite:0x00007fdb51e28158>

SMILES for #<Metabolite:0x00007fdb51e28158>

INCHI for #<Metabolite:0x00007fdb51e28158>

Structure for #<Metabolite:0x00007fdb51e28158>

3D Structure for #<Metabolite:0x00007fdb51e28158>