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

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 01:47:03 UTC
Update Date2022-08-31 18:24:02 UTC
Metabolite IDMMDBc0031735
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
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007f920cd6fb78>

ChEBI
  Mrv0541 02241222362D          

 13 12  0  0  0  0            999 V2000
    5.8163   -3.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5295   -3.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427   -3.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427   -2.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9809   -2.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8163   -2.6634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -3.8907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9682   -1.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7195   -2.6726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9559   -3.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9559   -4.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6691   -3.4761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3989   -3.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  7  1  1  0  0  0  0
  6  1  2  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
 10  3  1  0  0  0  0
  5  4  1  0  0  0  0
  9  5  1  0  0  0  0
  8  5  2  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f920cd6fb78>

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3D SDF for #<Metabolite:0x00007f920cd6fb78>
ChEBI
  Mrv0541 02241222362D          

 13 12  0  0  0  0            999 V2000
    5.8163   -3.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5295   -3.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427   -3.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427   -2.6634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9809   -2.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8163   -2.6634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -3.8907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9682   -1.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7195   -2.6726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9559   -3.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9559   -4.7201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6691   -3.4761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3989   -3.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  7  1  1  0  0  0  0
  6  1  2  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
 10  3  1  0  0  0  0
  5  4  1  0  0  0  0
  9  5  1  0  0  0  0
  8  5  2  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031735

> <DATABASE_NAME>
MIME

> <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

> <FORMULA>
C7H8O6

> <MOLECULAR_WEIGHT>
188.1348

> <EXACT_MASS>
188.032087988

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
16.307944304698253

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(methoxycarbonyl)pent-2-enedioic acid

> <ALOGPS_LOGP>
-0.04

> <JCHEM_LOGP>
-0.1418095526666667

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.9323490324113575

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.006949353425346

> <JCHEM_PKA_STRONGEST_BASIC>
-6.913625151213809

> <JCHEM_POLAR_SURFACE_AREA>
100.89999999999999

> <JCHEM_REFRACTIVITY>
39.9996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(methoxycarbonyl)pent-2-enedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007f920cd6fb78>
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PDB for #<Metabolite:0x00007f920cd6fb78>
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

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3D PDB for #<Metabolite:0x00007f920cd6fb78>
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SMILES for #<Metabolite:0x00007f920cd6fb78>
COC(=O)C(\CC(O)=O)=C\C(O)=O
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INCHI for #<Metabolite:0x00007f920cd6fb78>
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+
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Synonyms
ValueSource
(e)-3-(Methoxycarbonyl)pent-2-enedioic acidGenerator
(e)-3-(Methoxycarbonyl)pent-2-enedioateChEBI
(2E)-3-(Methoxycarbonyl)pent-2-enedioateGenerator
Molecular FormulaC7H8O6
Average Mass188.1348
Monoisotopic Mass188.032087988
IUPAC Name(2E)-3-(methoxycarbonyl)pent-2-enedioic acid
Traditional Name(2E)-3-(methoxycarbonyl)pent-2-enedioic acid
CAS Registry NumberNot 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 KeyBRYKYSQCLNCYQW-DUXPYHPUSA-N