Showing metabocard for Itaconic acid (MMDBc0000212)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-10-27 23:39:57 UTC
Update Date2024-10-09 15:39:16 UTC
Metabolite IDMMDBc0000212
Metabolite Identification
Common NameItaconic acid
DescriptionItaconic acid is an intermediate in the C5-Branched dibasic acid metabolism, a substrate for the enzyme Succinate-CoA ligase (ADP-forming) (EC:6.2.1.5)(Kegg). It has been found to be a metabolite in Aspergillus, Escherichia and Saccharomyces (PMID: 26360870 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00005645c65c73f0>


  Mrv1652305201900032D          

  9  8  0  0  0  0            999 V2000
   18.0688  -11.8270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6413  -12.2396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7833  -13.0646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9267  -11.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4978  -11.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7833  -12.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9267  -11.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2123  -12.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2123  -13.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00005645c65c73f0>

HMDB0002092
     RDKit          3D
Itaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    0.4939    1.7886    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291    0.4933   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5857   -0.4208   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289    0.0801   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2986    1.2535   -0.2507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600   -0.8639   -0.5964 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8757   -0.1248   -0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596    0.6209    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9630   -1.4864   -0.2929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139    2.3336    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150    2.3415    0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082   -1.2217    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041   -0.9627   -1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473   -1.8376   -0.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8126   -1.9936   -0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  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
  3 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:0x00005645c65c73f0>


  Mrv1652305201900032D          

  9  8  0  0  0  0            999 V2000
   18.0688  -11.8270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6413  -12.2396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7833  -13.0646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9267  -11.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4978  -11.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7833  -12.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9267  -11.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2123  -12.2396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2123  -13.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000212

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)CC(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)

> <INCHI_KEY>
LVHBHZANLOWSRM-UHFFFAOYSA-N

> <FORMULA>
C5H6O4

> <MOLECULAR_WEIGHT>
130.0987

> <EXACT_MASS>
130.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.058996822042474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylidenebutanedioic acid

> <ALOGPS_LOGP>
0.00

> <JCHEM_LOGP>
0.052824681999999894

> <ALOGPS_LOGS>
-0.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.492219330986345

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6521044530966424

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
27.9149

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
itaconic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00005645c65c73f0>

HMDB0002092
     RDKit          3D
Itaconic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    0.4939    1.7886    0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291    0.4933   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5857   -0.4208   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9289    0.0801   -0.3840 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2986    1.2535   -0.2507 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600   -0.8639   -0.5964 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8757   -0.1248   -0.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8596    0.6209    0.0700 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9630   -1.4864   -0.2929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4139    2.3336    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150    2.3415    0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5082   -1.2217    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4041   -0.9627   -1.3343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473   -1.8376   -0.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8126   -1.9936   -0.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  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
  3 12  1  0
  3 13  1  0
  6 14  1  0
  9 15  1  0
M  END
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PDB for #<Metabolite:0x00005645c65c73f0>

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  O   UNK     0      33.728 -22.077   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      40.397 -22.847   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.062 -24.387   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      39.063 -20.537   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      36.396 -22.077   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.062 -22.847   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      39.063 -22.077   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      37.730 -22.847   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.730 -24.387   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    6                                                            
CONECT    4    7                                                            
CONECT    5    6    8                                                       
CONECT    6    1    3    5                                                  
CONECT    7    2    4    8                                                  
CONECT    8    5    7    9                                                  
CONECT    9    8                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for #<Metabolite:0x00005645c65c73f0>

COMPND    HMDB0002092
HETATM    1  C1  UNL     1       0.494   1.789   0.045  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.529   0.493  -0.132  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.586  -0.421  -0.347  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.929   0.080  -0.384  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.299   1.254  -0.251  1.00  0.00           O  
HETATM    6  O2  UNL     1      -2.960  -0.864  -0.596  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.876  -0.125  -0.111  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.860   0.621   0.070  1.00  0.00           O  
HETATM    9  O4  UNL     1       1.963  -1.486  -0.293  1.00  0.00           O  
HETATM   10  H1  UNL     1       1.414   2.334   0.193  1.00  0.00           H  
HETATM   11  H2  UNL     1      -0.415   2.342   0.049  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.508  -1.222   0.461  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.404  -0.963  -1.334  1.00  0.00           H  
HETATM   14  H5  UNL     1      -2.847  -1.838  -0.339  1.00  0.00           H  
HETATM   15  H6  UNL     1       2.813  -1.994  -0.226  1.00  0.00           H  
CONECT    1    2    2   10   11
CONECT    2    3    7
CONECT    3    4   12   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:0x00005645c65c73f0>

OC(=O)CC(=C)C(O)=O
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INCHI for #<Metabolite:0x00005645c65c73f0>

InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
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Synonyms
ValueSource
2-Methylenesuccinic acidChEBI
2-Propene-1,2-dicarboxylic acidChEBI
Methylenebutanedioic acidChEBI
Methylenesuccinic acidChEBI
Propylenedicarboxylic acidChEBI
2-MethylenesuccinateGenerator
2-Propene-1,2-dicarboxylateGenerator
MethylenebutanedioateGenerator
MethylenesuccinateGenerator
PropylenedicarboxylateGenerator
ItaconateGenerator
2-Hydroxy-3-naphthoyl-2-naphthylamineHMDB
Itaconic acid, copper saltHMDB
Itaconic acid, disodium saltHMDB
Itaconic acid, calcium saltHMDB
Itaconic acid, sodium saltHMDB
Molecular FormulaC5H6O4
Average Mass130.0987
Monoisotopic Mass130.02660868
IUPAC Name2-methylidenebutanedioic acid
Traditional Nameitaconic acid
CAS Registry Number97-65-4
SMILES
OC(=O)CC(=C)C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h1-2H2,(H,6,7)(H,8,9)
InChI KeyLVHBHZANLOWSRM-UHFFFAOYSA-N