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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-18 17:48:17 UTC

Update Date

2019-07-23 07:14:48 UTC

HMDB ID

HMDB0060663

Secondary Accession Numbers

HMDB60663

Metabolite Identification

Common Name

Isoniazid alpha-ketoglutaric acid

Description

Isoniazid alpha-ketoglutaric acid, also known as isoniazid α-ketoglutarate, belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. Pyridinecarboxylic acids and derivatives are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof. Isoniazid alpha-ketoglutaric acid is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0060663
     RDKit          3D
Isoniazid alpha-ketoglutaric acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.1379    0.5144    1.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    1.1440    0.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7478    1.5921   -0.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    1.3764    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235    0.3661   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8297   -1.0054   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -1.4859    0.4919 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3778   -0.6801    0.5924 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518   -1.1259   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061   -2.2151   -0.6631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7761   -0.3208    0.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7435    0.9784    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356    1.7057    0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000    1.1084    0.1731 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1478   -0.1880   -0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9943   -0.9123   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464   -1.7920   -0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0416   -1.3387   -0.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0849   -3.0460    0.4055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824    2.4413   -0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8611    1.3860    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    2.4125   -0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271    0.4453   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320    0.6116   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739    0.2163    1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8026    1.4831    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484    2.7320    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0931   -0.6764   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789   -1.9718   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815   -3.7552    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 16 11  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  8 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 19 30  1  0
M  END

 
  Mrv1652303111920362D          

 19 19  0  0  0  0            999 V2000
   23.5178  -20.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2327  -20.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8062  -20.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5178  -19.6169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9478  -20.4419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2327  -21.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0877  -20.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8062  -19.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6663  -20.8545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0877  -19.6169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.3718  -20.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0758  -20.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3698  -19.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7750  -20.4428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0778  -21.6716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0877  -19.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0856  -18.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3622  -17.9692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7901  -17.9752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  7 10  2  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  2  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060663

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC\C(=N/NC(=O)C1=CC=NC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H11N3O5/c15-9(16)2-1-8(11(18)19)13-14-10(17)7-3-5-12-6-4-7/h3-6H,1-2H2,(H,14,17)(H,15,16)(H,18,19)/b13-8+

> <INCHI_KEY>
CCBSJXHUMYNUKH-MDWZMJQESA-N

> <FORMULA>
C11H11N3O5

> <MOLECULAR_WEIGHT>
265.2221

> <EXACT_MASS>
265.069870477

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
24.201728603753793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-2-{[(pyridin-4-yl)formamido]imino}pentanedioic acid

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.9926946376538723

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.9381400012166274

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9342489814264767

> <JCHEM_PKA_STRONGEST_BASIC>
4.088766173590029

> <JCHEM_POLAR_SURFACE_AREA>
128.95

> <JCHEM_REFRACTIVITY>
62.31960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoniazid α-ketoglutaric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060663
     RDKit          3D
Isoniazid alpha-ketoglutaric acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.1379    0.5144    1.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    1.1440    0.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7478    1.5921   -0.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    1.3764    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235    0.3661   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8297   -1.0054   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -1.4859    0.4919 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3778   -0.6801    0.5924 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518   -1.1259   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061   -2.2151   -0.6631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7761   -0.3208    0.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7435    0.9784    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356    1.7057    0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000    1.1084    0.1731 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1478   -0.1880   -0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9943   -0.9123   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464   -1.7920   -0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0416   -1.3387   -0.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0849   -3.0460    0.4055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824    2.4413   -0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8611    1.3860    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    2.4125   -0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271    0.4453   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320    0.6116   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739    0.2163    1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8026    1.4831    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484    2.7320    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0931   -0.6764   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789   -1.9718   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815   -3.7552    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 16 11  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  8 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 19 30  1  0
M  END

HEADER    PROTEIN                                 11-MAR-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-MAR-19         0                                  
HETATM    1  C   UNK     0      43.900 -38.158   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      45.234 -38.928   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      42.571 -38.928   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      43.900 -36.618   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      46.569 -38.158   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0      45.234 -40.468   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      41.230 -38.158   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      42.571 -35.842   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      47.911 -38.928   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      41.230 -36.618   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      49.227 -38.163   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      50.542 -38.918   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      49.224 -36.617   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      51.847 -38.160   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      50.545 -40.454   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      50.564 -35.838   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      50.560 -34.318   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      49.209 -33.543   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      51.875 -33.554   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2                                                            
CONECT    7    3   10                                                       
CONECT    8    4   10                                                       
CONECT    9    5   11                                                       
CONECT   10    7    8                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11   14   15                                                  
CONECT   13   11   16                                                       
CONECT   14   12                                                            
CONECT   15   12                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0060663
HETATM    1  O1  UNL     1      -4.138   0.514   1.541  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.772   1.144   0.514  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.748   1.592  -0.353  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.350   1.376   0.281  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.724   0.366  -0.621  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.830  -1.005  -0.102  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.766  -1.486   0.492  1.00  0.00           N  
HETATM    8  N2  UNL     1       0.378  -0.680   0.592  1.00  0.00           N  
HETATM    9  C5  UNL     1       1.552  -1.126  -0.029  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.606  -2.215  -0.663  1.00  0.00           O  
HETATM   11  C6  UNL     1       2.776  -0.321   0.045  1.00  0.00           C  
HETATM   12  C7  UNL     1       2.743   0.978   0.419  1.00  0.00           C  
HETATM   13  C8  UNL     1       3.936   1.706   0.483  1.00  0.00           C  
HETATM   14  N3  UNL     1       5.100   1.108   0.173  1.00  0.00           N  
HETATM   15  C9  UNL     1       5.148  -0.188  -0.202  1.00  0.00           C  
HETATM   16  C10 UNL     1       3.994  -0.912  -0.270  1.00  0.00           C  
HETATM   17  C11 UNL     1      -3.046  -1.792  -0.182  1.00  0.00           C  
HETATM   18  O4  UNL     1      -4.042  -1.339  -0.774  1.00  0.00           O  
HETATM   19  O5  UNL     1      -3.085  -3.046   0.405  1.00  0.00           O  
HETATM   20  H1  UNL     1      -4.682   2.441  -0.905  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.861   1.386   1.296  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.146   2.413  -0.109  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.127   0.445  -1.667  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.632   0.612  -0.767  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.374   0.216   1.108  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.803   1.483   0.671  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.848   2.732   0.787  1.00  0.00           H  
HETATM   28  H9  UNL     1       6.093  -0.676  -0.455  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.979  -1.972  -0.570  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.382  -3.755   0.152  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7    7   17
CONECT    7    8
CONECT    8    9   25
CONECT    9   10   10   11
CONECT   11   12   12   16
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   14   15
CONECT   15   16   16   28
CONECT   16   29
CONECT   17   18   18   19
CONECT   19   30
END

HMDB0060663
     RDKit          3D
Isoniazid alpha-ketoglutaric acid
 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.1379    0.5144    1.5412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7719    1.1440    0.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7478    1.5921   -0.3526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    1.3764    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7235    0.3661   -0.6213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8297   -1.0054   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -1.4859    0.4919 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3778   -0.6801    0.5924 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518   -1.1259   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061   -2.2151   -0.6631 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7761   -0.3208    0.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7435    0.9784    0.4191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356    1.7057    0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000    1.1084    0.1731 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1478   -0.1880   -0.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9943   -0.9123   -0.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464   -1.7920   -0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0416   -1.3387   -0.7743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0849   -3.0460    0.4055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824    2.4413   -0.9048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8611    1.3860    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1462    2.4125   -0.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271    0.4453   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320    0.6116   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739    0.2163    1.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8026    1.4831    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484    2.7320    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0931   -0.6764   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9789   -1.9718   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3815   -3.7552    0.1523 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 16 11  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  8 25  1  0
 12 26  1  0
 13 27  1  0
 15 28  1  0
 16 29  1  0
 19 30  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Isoniazid a-ketoglutarate	Generator
Isoniazid a-ketoglutaric acid	Generator
Isoniazid alpha-ketoglutarate	Generator
Isoniazid α-ketoglutarate	Generator
Isoniazid α-ketoglutaric acid	Generator

Chemical Formula

C₁₁H₁₁N₃O₅

Average Molecular Weight

265.2221

Monoisotopic Molecular Weight

265.069870477

IUPAC Name

(2E)-2-{[(pyridin-4-yl)formamido]imino}pentanedioic acid

Traditional Name

isoniazid α-ketoglutaric acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC\C(=N/NC(=O)C1=CC=NC=C1)C(O)=O

InChI Identifier

InChI=1S/C11H11N3O5/c15-9(16)2-1-8(11(18)19)13-14-10(17)7-3-5-12-6-4-7/h3-6H,1-2H2,(H,14,17)(H,15,16)(H,18,19)/b13-8+

InChI Key

CCBSJXHUMYNUKH-MDWZMJQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. Pyridinecarboxylic acids and derivatives are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids and derivatives

Alternative Parents

Substituents

Pyridine carboxylic acid or derivatives
Dicarboxylic acid or derivatives
Heteroaromatic compound
Azacycle
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:80619 )

Ontology

Not Available

Liver (HMDB: HMDB0060663)
Kidney (HMDB: HMDB0060663)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060663)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060663)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	-0.44	ALOGPS
logP	-0.99	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	1.93	ChemAxon
pKa (Strongest Basic)	4.09	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	128.95 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	62.32 m³·mol⁻¹	ChemAxon
Polarizability	24.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	163.173	30932474
DeepCCS	[M-H]-	160.815	30932474
DeepCCS	[M-2H]-	193.701	30932474
DeepCCS	[M+Na]+	169.266	30932474
AllCCS	[M+H]+	157.2	32859911
AllCCS	[M+H-H2O]+	153.8	32859911
AllCCS	[M+NH4]+	160.3	32859911
AllCCS	[M+Na]+	161.2	32859911
AllCCS	[M-H]-	157.7	32859911
AllCCS	[M+Na-2H]-	157.8	32859911
AllCCS	[M+HCOO]-	157.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoniazid alpha-ketoglutaric acid	OC(=O)CC\C(=N/NC(=O)C1=CC=NC=C1)C(O)=O	3072.4	Standard polar	33892256
Isoniazid alpha-ketoglutaric acid	OC(=O)CC\C(=N/NC(=O)C1=CC=NC=C1)C(O)=O	1588.5	Standard non polar	33892256
Isoniazid alpha-ketoglutaric acid	OC(=O)CC\C(=N/NC(=O)C1=CC=NC=C1)C(O)=O	2473.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoniazid alpha-ketoglutaric acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC/C(=N\NC(=O)C1=CC=NC=C1)C(=O)O	2595.3	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)/C(CCC(=O)O)=N/NC(=O)C1=CC=NC=C1	2485.4	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,1TMS,isomer #3	C[Si](C)(C)N(/N=C(\CCC(=O)O)C(=O)O)C(=O)C1=CC=NC=C1	2549.7	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC/C(=N\NC(=O)C1=CC=NC=C1)C(=O)O[Si](C)(C)C	2442.2	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)CC/C(=N\N(C(=O)C1=CC=NC=C1)[Si](C)(C)C)C(=O)O	2484.5	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)/C(CCC(=O)O)=N/N(C(=O)C1=CC=NC=C1)[Si](C)(C)C	2435.7	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC/C(=N\N(C(=O)C1=CC=NC=C1)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2403.6	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC/C(=N\N(C(=O)C1=CC=NC=C1)[Si](C)(C)C)C(=O)O[Si](C)(C)C	2264.0	Standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC/C(=N\N(C(=O)C1=CC=NC=C1)[Si](C)(C)C)C(=O)O[Si](C)(C)C	3106.7	Standard polar	33892256
Isoniazid alpha-ketoglutaric acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC/C(=N\NC(=O)C1=CC=NC=C1)C(=O)O	2829.5	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)/C(CCC(=O)O)=N/NC(=O)C1=CC=NC=C1	2725.9	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(/N=C(\CCC(=O)O)C(=O)O)C(=O)C1=CC=NC=C1	2768.0	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC/C(=N\NC(=O)C1=CC=NC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2862.2	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC/C(=N\N(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)C(=O)O	2918.4	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)/C(CCC(=O)O)=N/N(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C	2876.5	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC/C(=N\N(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3003.0	Semi standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC/C(=N\N(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2771.2	Standard non polar	33892256
Isoniazid alpha-ketoglutaric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC/C(=N\N(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3334.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoniazid alpha-ketoglutaric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0avm-5980000000-2d2e5e2030d38c582913	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoniazid alpha-ketoglutaric acid GC-MS (2 TMS) - 70eV, Positive	splash10-05fu-8976000000-3198c6f799643371a12e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoniazid alpha-ketoglutaric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoniazid alpha-ketoglutaric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 10V, Positive-QTOF	splash10-052b-0390000000-046e495b2091100c28e8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 20V, Positive-QTOF	splash10-0ab9-1890000000-4d20806ed33521cf139b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 40V, Positive-QTOF	splash10-0a4i-8900000000-f62766039d8b6a2fc3f8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 10V, Negative-QTOF	splash10-03fs-0490000000-bf7471b5b08f4831141b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 20V, Negative-QTOF	splash10-00ca-1950000000-06f000bb1cc49174dc77	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 40V, Negative-QTOF	splash10-002f-9400000000-621a4ddea170f73ac950	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 10V, Positive-QTOF	splash10-066s-0490000000-1efa0b38204208e180b1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 20V, Positive-QTOF	splash10-0a4i-1910000000-1cb2eab137fc01381f64	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 40V, Positive-QTOF	splash10-053r-9700000000-633e6ba5cb0edcab1f86	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 10V, Negative-QTOF	splash10-0229-0960000000-1ea40cc4a468eee94534	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 20V, Negative-QTOF	splash10-00di-6930000000-284d85ecc1107a976e3c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoniazid alpha-ketoglutaric acid 40V, Negative-QTOF	splash10-0007-9300000000-2e9610773a22ee6a1123	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16625

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9576951

PDB ID

Not Available

ChEBI ID

80619

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Isoniazid alpha-ketoglutaric acid (HMDB0060663)

MOL for HMDB0060663 (Isoniazid alpha-ketoglutaric acid)

3D MOL for HMDB0060663 (Isoniazid alpha-ketoglutaric acid)

3D SDF for HMDB0060663 (Isoniazid alpha-ketoglutaric acid)

3D-SDF for HMDB0060663 (Isoniazid alpha-ketoglutaric acid)

PDB for HMDB0060663 (Isoniazid alpha-ketoglutaric acid)

3D PDB for HMDB0060663 (Isoniazid alpha-ketoglutaric acid)

SMILES for HMDB0060663 (Isoniazid alpha-ketoglutaric acid)

INCHI for HMDB0060663 (Isoniazid alpha-ketoglutaric acid)

Structure for HMDB0060663 (Isoniazid alpha-ketoglutaric acid)

3D Structure for HMDB0060663 (Isoniazid alpha-ketoglutaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra