Showing metabocard for Mesaconic acid (MMDBc0047913)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-23 23:14:42 UTC
Update Date2024-04-30 20:32:23 UTC
Metabolite IDMMDBc0047913
Metabolite Identification
Common NameMesaconic acid
DescriptionMesaconic acid, also known as 2-methylfumarate or citronic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Mesaconic acid is a dicarboxylic butenoic acid, with a methyl group in position 2 and the double bound between carbons 2 and 3. Mesaconic acid was first studied for its physical properties in 1874 by Jacobus van ‘t Hoff (https://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van%27t-Hoff-1874.html). It is now known to be involved in the biosynthesis of vitamin B12 and it is also a competitor inhibitor of the reduction of fumarate.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fed080438d0>


  Mrv1652305271900202D          

  9  8  0  0  0  0            999 V2000
   -2.0087    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -0.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087    1.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5798    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.9589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491    0.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fed080438d0>

HMDB0000749
     RDKit          3D
Mesaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.0546    1.1373    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199    0.0960   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.6398   -0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.4114   -0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457   -1.1216   -1.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3062    0.5342    0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -0.1657   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659    0.5381    0.3320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4157   -1.1344   -1.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834    1.9793    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    1.6453    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4733    0.7713    1.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616   -1.4257   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003    0.3349    1.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2692   -2.1377   -1.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  6 14  1  0
  9 15  1  0
M  END
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3D SDF for #<Metabolite:0x00007fed080438d0>


  Mrv1652305271900202D          

  9  8  0  0  0  0            999 V2000
   -2.0087    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -0.1339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0087    1.1035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5798    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346   -0.9589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8491    0.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047913

> <DATABASE_NAME>
MIME

> <SMILES>
C\C(=C/C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+

> <INCHI_KEY>
HNEGQIOMVPPMNR-NSCUHMNNSA-N

> <FORMULA>
C5H6O4

> <MOLECULAR_WEIGHT>
130.0987

> <EXACT_MASS>
130.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.241128315164042

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-2-methylbut-2-enedioic acid

> <ALOGPS_LOGP>
0.21

> <JCHEM_LOGP>
0.35463615800000003

> <ALOGPS_LOGS>
-0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.568292663140774

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.722300394674801

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
28.964100000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mesaconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fed080438d0>

HMDB0000749
     RDKit          3D
Mesaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -0.0546    1.1373    0.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5199    0.0960   -0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -0.6398   -0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7898   -0.4114   -0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457   -1.1216   -1.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3062    0.5342    0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -0.1657   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7659    0.5381    0.3320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4157   -1.1344   -1.1488 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834    1.9793    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9778    1.6453    1.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4733    0.7713    1.7621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616   -1.4257   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8003    0.3349    1.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2692   -2.1377   -1.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  2  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  6 14  1  0
  9 15  1  0
M  END
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PDB for #<Metabolite:0x00007fed080438d0>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -3.750   0.520   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.083  -0.250   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -3.750   2.060   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.416  -0.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.416  -1.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.082   0.520   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.251  -0.250   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.251  -1.790   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.585   0.520   0.000  0.00  0.00           O+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for #<Metabolite:0x00007fed080438d0>

COMPND    HMDB0000749
HETATM    1  C1  UNL     1      -0.055   1.137   0.875  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.520   0.096  -0.050  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.379  -0.640  -0.699  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.790  -0.411  -0.490  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.646  -1.122  -1.116  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.306   0.534   0.350  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.936  -0.166  -0.288  1.00  0.00           C  
HETATM    8  O3  UNL     1      -2.766   0.538   0.332  1.00  0.00           O  
HETATM    9  O4  UNL     1      -2.416  -1.134  -1.149  1.00  0.00           O  
HETATM   10  H1  UNL     1       0.483   1.979   0.368  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.978   1.645   1.289  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.473   0.771   1.762  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.062  -1.426  -1.397  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.800   0.335   1.222  1.00  0.00           H  
HETATM   15  H6  UNL     1      -2.269  -2.138  -1.009  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    7
CONECT    3    4   13
CONECT    4    5    5    6
CONECT    6   14
CONECT    7    8    8    9
CONECT    9   15
END
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SMILES for #<Metabolite:0x00007fed080438d0>

C\C(=C/C(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007fed080438d0>

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
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Synonyms
ValueSource
(e)-2-Methyl-2-butenedioic acidChEBI
(e)-Citraconic acidChEBI
2-Methylfumaric acidChEBI
Citronic acidChEBI
Methylfumaric acidChEBI
trans-1-Propene-1,2-dicarboxylic acidChEBI
trans-2-Methyl-2-butenedioic acidChEBI
2-MethylfumarateKegg
(e)-2-Methyl-2-butenedioateGenerator
(e)-CitraconateGenerator
CitronateGenerator
MethylfumarateGenerator
trans-1-Propene-1,2-dicarboxylateGenerator
trans-2-Methyl-2-butenedioateGenerator
MesaconateGenerator
(Z)-2-Methyl-2-butenedioic acidHMDB
Citraconic acidHMDB
Citraconic acid, (e)-isomerHMDB
Citraconic acid, ammonium saltHMDB
Citraconic acid, calcium saltHMDB
Citraconic acid, sodium saltHMDB
Methylmaleic acidHMDB
MonomethylfumarateHMDB
(2E)-2-Methyl-2-butenedioateHMDB
(2E)-2-Methyl-2-butenedioic acidHMDB
Molecular FormulaC5H6O4
Average Mass130.0987
Monoisotopic Mass130.02660868
IUPAC Name(2E)-2-methylbut-2-enedioic acid
Traditional Namemesaconic acid
CAS Registry Number498-24-8
SMILES
C\C(=C/C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
InChI KeyHNEGQIOMVPPMNR-NSCUHMNNSA-N