MiMeDB: Showing metabocard for E-3-Carboxy-2-pentenedioate 6-methyl ester (MMDBc0031609)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:41:16 UTC

Update Date

2022-08-31 18:22:28 UTC

Metabolite ID

MMDBc0031609

Metabolite Identification

Common Name

E-3-Carboxy-2-pentenedioate 6-methyl ester

Description

E-3-carboxy-2-pentenedioate 6-methyl ester is catalyzed by trans-aconitate methyltransferase. The trans-aconitate methyltransferase from the bacterium Escherichia coli catalyzes the monomethyl esterification of trans-aconitate and related compounds. Using two-dimensional (1)H/(13)C nuclear magnetic resonance spectroscopy, we show that the methylation is specific to one of the three carboxyl groups and further demonstrate that the product is the 6-methyl ester of trans-aconitate (E-3-carboxy-2-pentenedioate 6-methyl ester). (PMID 11329290 )

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 08141218152D          

 14 13  0  0  0  0            999 V2000
    0.8250    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184   -1.2375    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.6039    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3184    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  1  1  0  0  0  0
 13  7  1  0  0  0  0
 14  2  1  0  0  0  0
M  CHG  2   9  -1  11  -1
M  END
> <DATABASE_ID>
MMDBc0031609

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(C([O-])=O)=C(\CC([O-])=O)C(=O)OC

> <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)/p-2/b4-2+

> <INCHI_KEY>
BRYKYSQCLNCYQW-DUXPYHPUSA-L

> <FORMULA>
C7H6O6

> <MOLECULAR_WEIGHT>
186.1189

> <EXACT_MASS>
186.016437924

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
15.546301083713221

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(methoxycarbonyl)pent-2-enedioate

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
-0.1418095526666667

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.9323490324113575

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.006949353425347

> <JCHEM_PKA_STRONGEST_BASIC>
-6.913625151213809

> <JCHEM_POLAR_SURFACE_AREA>
106.55999999999999

> <JCHEM_REFRACTIVITY>
61.6738

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(methoxycarbonyl)pent-2-enedioate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-AUG-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-AUG-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2    4    5   14                                                  
CONECT    3    4    6                                                       
CONECT    4    2    3    7                                                  
CONECT    5    2    8    9                                                  
CONECT    6    3   10   11                                                  
CONECT    7    4   12   13                                                  
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    1    7                                                       
CONECT   14    2                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

Synonyms

Value	Source
(2E)-3-(Methoxycarbonyl)pent-2-enedioate dianion	ChEBI
(e)-3-(Methoxycarbonyl)pent-2-enedioate	ChEBI
(2E)-3-(Methoxycarbonyl)pent-2-enedioic acid dianion	Generator
(e)-3-(Methoxycarbonyl)pent-2-enedioic acid	Generator
e-3-Carboxy-2-pentenedioic acid 6-methyl ester	Generator
(2E)-3-(Methoxycarbonyl)pent-2-enedioic acid(2-)	Generator

Molecular Formula

C₇H₆O₆

Average Mass

186.1189

Monoisotopic Mass

186.016437924

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]\C(C([O-])=O)=C(\CC([O-])=O)C(=O)OC

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)/p-2/b4-2+

InChI Key

BRYKYSQCLNCYQW-DUXPYHPUSA-L

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
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

dicarboxylic acid dianion (CHEBI:57470 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	13 g/L	ALOGPS
logP	0.21	ALOGPS
logP	-0.14	ChemAxon
logS	-1.2	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	0	ChemAxon
Polar Surface Area	106.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	61.67 m³·mol⁻¹	ChemAxon
Polarizability	15.55 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-29cf6db631c4e5fb8bd6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002r-0900000000-54941234d0e303e3472f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02bk-1900000000-c8645cf8508af43e465c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-da67d4e803c2ed35d157	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-e86dd93cf5da87063ef7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-9800000000-2413ebf49261aab9a389	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

Feces

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

Not Available

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	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23615417

PDB ID

Not Available

ChEBI ID

57470

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Cai H, Strouse J, Dumlao D, Jung ME, Clarke S: Distinct reactions catalyzed by bacterial and yeast trans-aconitate methyltransferases. Biochemistry. 2001 Feb 20;40(7):2210-9. doi: 10.1021/bi0022902. [PubMed:11329290 ]
van der Werf MJ, Overkamp KM, Muilwijk B, Coulier L, Hankemeier T: Microbial metabolomics: toward a platform with full metabolome coverage. Anal Biochem. 2007 Nov 1;370(1):17-25. doi: 10.1016/j.ab.2007.07.022. Epub 2007 Aug 1. [PubMed:17765195 ]

Showing metabocard for E-3-Carboxy-2-pentenedioate 6-methyl ester (MMDBc0031609)

MOL for #<Metabolite:0x00007f46ec904ef0>

3D MOL for #<Metabolite:0x00007f46ec904ef0>

3D SDF for #<Metabolite:0x00007f46ec904ef0>

3D-SDF for #<Metabolite:0x00007f46ec904ef0>

PDB for #<Metabolite:0x00007f46ec904ef0>

3D PDB for #<Metabolite:0x00007f46ec904ef0>

SMILES for #<Metabolite:0x00007f46ec904ef0>

INCHI for #<Metabolite:0x00007f46ec904ef0>

Structure for #<Metabolite:0x00007f46ec904ef0>

3D Structure for #<Metabolite:0x00007f46ec904ef0>