Showing metabocard for 2-Methylglutaric acid (MMDBc0000816)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 22:03:40 UTC
Update Date2024-04-30 19:33:45 UTC
Metabolite IDMMDBc0000816
Metabolite Identification
Common Name2-Methylglutaric acid
Description2-Methylglutaric acid, also known as alpha-methylglutarate or 2-methylpentanedioate, 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. 2-Methylglutaric acid is also classified as an alpha,omega-dicarboxylic acid. It is glutaric acid substituted at position 2 by a methyl group. 2-Methylglutaric acid arises from the microbial metabolism of the isoprenoid alkaloid pristane (PMID: 4327007 ; PMID: 20143352 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f925123db98>


  Mrv1652305261923542D          

 10  9  0  0  0  0            999 V2000
   10.9938   -9.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2793   -8.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7068   -9.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4214   -8.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5648   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8503   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1358   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5648  -10.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2793   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4214   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3 10  1  0  0  0  0
  4 10  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f925123db98>

HMDB0000422
     RDKit          3D
2-Methylglutaric acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -1.2582   -1.4926   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1097   -0.2330    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1451    0.5332   -0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773   -0.2946    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5884    0.4956   -0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4746    1.6732   -0.7291 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8675    0.0081   -0.1309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2783    0.6224   -0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2057    0.2250   -0.8500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    1.8662    0.4891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5733   -2.2751   -0.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433   -1.2959   -1.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3232   -1.8369   -0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0575   -0.4779    1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1617    1.4189    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706    0.8615   -1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2933   -1.2211   -0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3896   -0.5453    1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -0.7656    0.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1826    2.7338    0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  7 19  1  0
 10 20  1  0
M  END
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3D SDF for #<Metabolite:0x00007f925123db98>


  Mrv1652305261923542D          

 10  9  0  0  0  0            999 V2000
   10.9938   -9.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2793   -8.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7068   -9.4604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4214   -8.2229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5648   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8503   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1358   -9.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5648  -10.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2793   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4214   -9.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3 10  1  0  0  0  0
  4 10  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000816

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O4/c1-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)

> <INCHI_KEY>
AQYCMVICBNBXNA-UHFFFAOYSA-N

> <FORMULA>
C6H10O4

> <MOLECULAR_WEIGHT>
146.1412

> <EXACT_MASS>
146.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
13.956525275740471

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylpentanedioic acid

> <ALOGPS_LOGP>
0.33

> <JCHEM_LOGP>
0.5890719759999997

> <ALOGPS_LOGS>
-0.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.676174036855366

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8942615644961274

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
32.7125

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-methylglutaric acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for #<Metabolite:0x00007f925123db98>

HMDB0000422
     RDKit          3D
2-Methylglutaric acid
 20 19  0  0  0  0  0  0  0  0999 V2000
   -1.2582   -1.4926   -0.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1097   -0.2330    0.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1451    0.5332   -0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773   -0.2946    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5884    0.4956   -0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4746    1.6732   -0.7291 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8675    0.0081   -0.1309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2783    0.6224   -0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2057    0.2250   -0.8500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    1.8662    0.4891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5733   -2.2751   -0.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433   -1.2959   -1.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3232   -1.8369   -0.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0575   -0.4779    1.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1617    1.4189    0.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706    0.8615   -1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2933   -1.2211   -0.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3896   -0.5453    1.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -0.7656    0.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1826    2.7338    0.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  4 18  1  0
  7 19  1  0
 10 20  1  0
M  END
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PDB for #<Metabolite:0x00007f925123db98>

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      20.522 -17.659   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      19.188 -15.349   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.519 -17.659   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.853 -15.349   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      17.854 -17.659   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.521 -16.889   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.187 -17.659   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.854 -19.199   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.188 -16.889   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.853 -16.889   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   10                                                            
CONECT    5    6    8    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6   10                                                       
CONECT    8    5                                                            
CONECT    9    1    2    5                                                  
CONECT   10    3    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for #<Metabolite:0x00007f925123db98>

COMPND    HMDB0000422
HETATM    1  C1  UNL     1      -1.258  -1.493  -0.685  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.110  -0.233   0.096  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.145   0.533  -0.231  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.377  -0.295   0.052  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.588   0.496  -0.282  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.475   1.673  -0.729  1.00  0.00           O  
HETATM    7  O2  UNL     1       3.867   0.008  -0.131  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.278   0.622  -0.100  1.00  0.00           C  
HETATM    9  O3  UNL     1      -3.206   0.225  -0.850  1.00  0.00           O  
HETATM   10  O4  UNL     1      -2.451   1.866   0.489  1.00  0.00           O  
HETATM   11  H1  UNL     1      -0.573  -2.275  -0.304  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.143  -1.296  -1.769  1.00  0.00           H  
HETATM   13  H3  UNL     1      -2.323  -1.837  -0.561  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.057  -0.478   1.195  1.00  0.00           H  
HETATM   15  H5  UNL     1       0.162   1.419   0.445  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.171   0.862  -1.273  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.293  -1.221  -0.545  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.390  -0.545   1.120  1.00  0.00           H  
HETATM   19  H9  UNL     1       4.115  -0.766   0.471  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.183   2.734   0.027  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    8   14
CONECT    3    4   15   16
CONECT    4    5   17   18
CONECT    5    6    6    7
CONECT    7   19
CONECT    8    9    9   10
CONECT   10   20
END
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SMILES for #<Metabolite:0x00007f925123db98>

CC(CCC(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007f925123db98>

InChI=1S/C6H10O4/c1-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)
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Synonyms
ValueSource
alpha-Methylglutaric acidChEBI
a-MethylglutarateGenerator
a-Methylglutaric acidGenerator
alpha-MethylglutarateGenerator
Α-methylglutarateGenerator
Α-methylglutaric acidGenerator
2-MethylglutarateGenerator
(+-)-2-Methylglutaric acidHMDB
2-MethylpentanedioateHMDB
2-Methylpentanedioic acidHMDB
2-Methyleneglutaric acidHMDB
2-MethyleneglutarateHMDB
alpha-Methylene glutarateHMDB
alpha-Methylene glutarate, ion(2-)HMDB
2-Methylene glutarateHMDB
2-Methyl-glutarateHMDB
Molecular FormulaC6H10O4
Average Mass146.1412
Monoisotopic Mass146.057908808
IUPAC Name2-methylpentanedioic acid
Traditional Nameα-methylglutaric acid
CAS Registry NumberNot Available
SMILES
CC(CCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O4/c1-4(6(9)10)2-3-5(7)8/h4H,2-3H2,1H3,(H,7,8)(H,9,10)
InChI KeyAQYCMVICBNBXNA-UHFFFAOYSA-N