Showing metabocard for Citraconic acid (MMDBc0030355)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-18 00:04:59 UTC
Update Date2024-10-11 01:10:25 UTC
Metabolite IDMMDBc0030355
Metabolite Identification
Common NameCitraconic acid
DescriptionMesaconic acid is one of several isomeric carboxylic acids obtained from citric acid. Is used as a fire retardant, recent studies revealed this acid is a competitive inhibitor of fumarate reduction.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fdb6cd24ac0>


  Mrv1652309042000042D          

  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
   -0.5798    1.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942    1.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346    1.5160    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
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fdb6cd24ac0>

HMDB0000634
     RDKit          3D
Citraconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.6418   -1.2910    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457   -0.2449    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657   -0.4613   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    0.2920   -0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614    1.3498    0.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8088   -0.1972   -1.2591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    0.8988    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865    0.9739    1.5794 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837    1.9177    1.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -1.2208   -0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1290   -2.2655    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -1.1705    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5664   -1.4050   -1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389   -0.0846   -2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346    2.9087    1.2284 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
Download

3D SDF for #<Metabolite:0x00007fdb6cd24ac0>


  Mrv1652309042000042D          

  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
   -0.5798    1.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2942    1.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1346    1.5160    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
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030355

> <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-IHWYPQMZSA-N

> <FORMULA>
C5H6O4

> <MOLECULAR_WEIGHT>
130.0987

> <EXACT_MASS>
130.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.166206395628047

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-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>
5.792150443903295

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4984426139122826

> <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>
citraconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007fdb6cd24ac0>

HMDB0000634
     RDKit          3D
Citraconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.6418   -1.2910    0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5457   -0.2449    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5657   -0.4613   -0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7639    0.2920   -0.4819 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614    1.3498    0.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8088   -0.1972   -1.2591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    0.8988    1.0252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865    0.9739    1.5794 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837    1.9177    1.3021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0818   -1.2208   -0.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1290   -2.2655    0.1737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4189   -1.1705    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5664   -1.4050   -1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8389   -0.0846   -2.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1346    2.9087    1.2284 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
Download

PDB for #<Metabolite:0x00007fdb6cd24ac0>

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         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      -1.082   2.060   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.416   2.830   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.251   2.830   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
Download

3D PDB for #<Metabolite:0x00007fdb6cd24ac0>

COMPND    HMDB0000634
HETATM    1  C1  UNL     1      -1.642  -1.291   0.028  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.546  -0.245   0.206  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.566  -0.461  -0.427  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.764   0.292  -0.482  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.961   1.350   0.104  1.00  0.00           O  
HETATM    6  O2  UNL     1       2.809  -0.197  -1.259  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.751   0.899   1.025  1.00  0.00           C  
HETATM    8  O3  UNL     1      -1.887   0.974   1.579  1.00  0.00           O  
HETATM    9  O4  UNL     1       0.084   1.918   1.302  1.00  0.00           O  
HETATM   10  H1  UNL     1      -2.082  -1.221  -0.977  1.00  0.00           H  
HETATM   11  H2  UNL     1      -1.129  -2.265   0.174  1.00  0.00           H  
HETATM   12  H3  UNL     1      -2.419  -1.170   0.794  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.566  -1.405  -1.029  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.839  -0.085  -2.266  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.135   2.909   1.228  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
Download

SMILES for #<Metabolite:0x00007fdb6cd24ac0>

C\C(=C\C(O)=O)C(O)=O
Download

INCHI for #<Metabolite:0x00007fdb6cd24ac0>

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-
Download
Synonyms
ValueSource
(Z)-2-Methyl-2-butenedioic acidChEBI
2-Methyl-2-butenedioic acidChEBI
2-Methylmaleic acidChEBI
alpha-Methylmaleic acidChEBI
cis-2-Methylbutenedioic acidChEBI
cis-Methylbutenedioic acidChEBI
CitraconsaeureChEBI
Methyl-maleinsaeureChEBI
Methylmaleic acidChEBI
CitraconateKegg
(Z)-2-Methyl-2-butenedioateGenerator
2-Methyl-2-butenedioateGenerator
2-MethylmaleateGenerator
a-MethylmaleateGenerator
a-Methylmaleic acidGenerator
alpha-MethylmaleateGenerator
Α-methylmaleateGenerator
Α-methylmaleic acidGenerator
cis-2-MethylbutenedioateGenerator
cis-MethylbutenedioateGenerator
MethylmaleateGenerator
Citraconic acid, ammonium saltHMDB
Citraconic acid, calcium saltHMDB
Citraconic acid, sodium saltHMDB
Methylfumaric acidHMDB
(e)-2-Methyl-2-butenedioic acidHMDB
Citraconic acid, (e)-isomerHMDB
Mesaconic acidHMDB
MonomethylfumarateHMDB
Molecular FormulaC5H6O4
Average Mass130.0987
Monoisotopic Mass130.02660868
IUPAC Name(2Z)-2-methylbut-2-enedioic acid
Traditional Namecitraconic acid
CAS Registry Number498-23-7
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-IHWYPQMZSA-N