Showing metabocard for Cis-2-Methylaconitate (MMDBc0029828)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:43:22 UTC
Update Date2024-04-30 19:42:36 UTC
Metabolite IDMMDBc0029828
Metabolite Identification
Common NameCis-2-Methylaconitate
Descriptioncis-2-Methylaconitate is produced due to the dehydration of 2-methylcitrate in 2-methylcitric acid cycle. The cycle is catalyzed by a cofactor-less (PrpD) enzyme or by an aconitase-like (AcnD) enzyme. (PMID: 17567742 )
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9209b51808>


  Mrv0541 02231220382D          

 13 12  0  0  0  0            999 V2000
   16.1042   -5.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -7.1405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622   -3.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -3.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1042   -5.9028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -3.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -5.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2478   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -6.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2478   -3.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4 11  2  0  0  0  0
  5 12  2  0  0  0  0
  6 13  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007f9209b51808>

HMDB0006357
     RDKit          3D
cis-2-Methylaconitate
 21 20  0  0  0  0  0  0  0  0999 V2000
   -0.7361   -1.6688   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -0.2207   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792    0.1819   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1797   -0.7695   -0.5221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0256    1.3138    0.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0580    0.4695    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4539    0.0651    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581   -1.2255    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8490   -2.1916    0.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6319   -1.5215   -1.1786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353    1.8952    0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286    2.4335    0.5833 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917    2.6629    0.9732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875   -2.0069   -1.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248   -2.3126    0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0180   -1.7550   -1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8454    1.4580    0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972    0.7888   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8676    0.4824    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994   -1.2059   -1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092    3.1270    0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 13 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f9209b51808>


  Mrv0541 02231220382D          

 13 12  0  0  0  0            999 V2000
   16.1042   -5.0778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -7.1405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622   -3.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -3.8403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1042   -5.9028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -3.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5332   -5.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2478   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9622   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -4.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8188   -6.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2478   -3.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4 11  2  0  0  0  0
  5 12  2  0  0  0  0
  6 13  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029828

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O6/c1-3(6(10)11)4(7(12)13)2-5(8)9/h2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/b4-3-

> <INCHI_KEY>
NUZLRKBHOBPTQV-ARJAWSKDSA-N

> <FORMULA>
C7H8O6

> <MOLECULAR_WEIGHT>
188.1348

> <EXACT_MASS>
188.032087988

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
15.548107198906383

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1Z)-1-methylprop-1-ene-1,2,3-tricarboxylic acid

> <ALOGPS_LOGP>
-0.33

> <JCHEM_LOGP>
-0.12548645266666678

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.8670232852737367

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.2458676878407497

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999998

> <JCHEM_REFRACTIVITY>
39.58760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-methylaconitate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9209b51808>

HMDB0006357
     RDKit          3D
cis-2-Methylaconitate
 21 20  0  0  0  0  0  0  0  0999 V2000
   -0.7361   -1.6688   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9918   -0.2207   -0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792    0.1819   -0.1189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1797   -0.7695   -0.5221 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0256    1.3138    0.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0580    0.4695    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4539    0.0651    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581   -1.2255    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8490   -2.1916    0.8139 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6319   -1.5215   -1.1786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353    1.8952    0.5995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2286    2.4335    0.5833 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917    2.6629    0.9732 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6875   -2.0069   -1.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248   -2.3126    0.3832 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0180   -1.7550   -1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8454    1.4580    0.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972    0.7888   -0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8676    0.4824    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994   -1.2059   -1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5092    3.1270    0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  6 11  1  0
 11 12  2  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  5 17  1  0
  7 18  1  0
  7 19  1  0
 10 20  1  0
 13 21  1  0
M  END
Download

PDB for #<Metabolite:0x00007f9209b51808>

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      30.061  -9.479   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      31.395 -13.329   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.396  -6.399   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      31.395  -7.169   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.061 -11.019   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      32.729  -6.399   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      32.729  -9.479   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.729 -11.019   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.063  -8.709   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.396  -9.479   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.395  -8.709   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.395 -11.789   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.063  -7.169   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6   13                                                            
CONECT    7    8    9   11                                                  
CONECT    8    7   12                                                       
CONECT    9    7   10   13                                                  
CONECT   10    9                                                            
CONECT   11    1    4    7                                                  
CONECT   12    2    5    8                                                  
CONECT   13    3    6    9                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END
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3D PDB for #<Metabolite:0x00007f9209b51808>

COMPND    HMDB0006357
HETATM    1  C1  UNL     1      -0.736  -1.669  -0.485  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.992  -0.221  -0.092  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.379   0.182  -0.119  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.180  -0.770  -0.522  1.00  0.00           O  
HETATM    5  O2  UNL     1      -3.026   1.314   0.180  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.058   0.470   0.242  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.454   0.065   0.305  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.958  -1.225   0.024  1.00  0.00           C  
HETATM    9  O3  UNL     1       1.849  -2.192   0.814  1.00  0.00           O  
HETATM   10  O4  UNL     1       2.632  -1.522  -1.179  1.00  0.00           O  
HETATM   11  C7  UNL     1      -0.135   1.895   0.600  1.00  0.00           C  
HETATM   12  O5  UNL     1      -1.229   2.433   0.583  1.00  0.00           O  
HETATM   13  O6  UNL     1       0.992   2.663   0.973  1.00  0.00           O  
HETATM   14  H1  UNL     1      -1.687  -2.007  -1.043  1.00  0.00           H  
HETATM   15  H2  UNL     1      -0.725  -2.313   0.383  1.00  0.00           H  
HETATM   16  H3  UNL     1       0.018  -1.755  -1.251  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.845   1.458   0.720  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.997   0.789  -0.417  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.868   0.482   1.304  1.00  0.00           H  
HETATM   20  H7  UNL     1       3.599  -1.206  -1.284  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.509   3.127   0.263  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    6    6
CONECT    3    4    4    5
CONECT    5   17
CONECT    6    7   11
CONECT    7    8   18   19
CONECT    8    9    9   10
CONECT   10   20
CONECT   11   12   12   13
CONECT   13   21
END
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SMILES for #<Metabolite:0x00007f9209b51808>

C\C(C(O)=O)=C(/CC(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007f9209b51808>

InChI=1S/C7H8O6/c1-3(6(10)11)4(7(12)13)2-5(8)9/h2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/b4-3-
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Synonyms
ValueSource
(Z)-But-2-ene-1,2,3-tricarboxylateChEBI
alpha-Methyl-cis-aconitateChEBI
alpha-MethylaconitateChEBI
cis-2-Butene-1,2,3-tricarboxylic acidChEBI
(Z)-But-2-ene-1,2,3-tricarboxylic acidGenerator
a-Methyl-cis-aconitateGenerator
a-Methyl-cis-aconitic acidGenerator
alpha-Methyl-cis-aconitic acidGenerator
Α-methyl-cis-aconitateGenerator
Α-methyl-cis-aconitic acidGenerator
a-MethylaconitateGenerator
a-Methylaconitic acidGenerator
alpha-Methylaconitic acidGenerator
Α-methylaconitateGenerator
Α-methylaconitic acidGenerator
cis-2-Butene-1,2,3-tricarboxylateGenerator
cis-2-Methylaconitic acidGenerator
(2Z)-But-2-ene-1,2,3-tricarboxylic acidHMDB
(Z)-2-Butene-1,2,3-tricarboxylic acidHMDB
Molecular FormulaC7H8O6
Average Mass188.1348
Monoisotopic Mass188.032087988
IUPAC Name(1Z)-1-methylprop-1-ene-1,2,3-tricarboxylic acid
Traditional Nameα-methylaconitate
CAS Registry Number6061-93-4
SMILES
C\C(C(O)=O)=C(/CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H8O6/c1-3(6(10)11)4(7(12)13)2-5(8)9/h2H2,1H3,(H,8,9)(H,10,11)(H,12,13)/b4-3-
InChI KeyNUZLRKBHOBPTQV-ARJAWSKDSA-N