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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 12:53:47 UTC

Update Date

2021-09-26 23:07:38 UTC

HMDB ID

HMDB0253981

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Laquinimod

Description

Laquinimod belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group. Laquinimod is an extremely weak basic (essentially neutral) compound (based on its pKa). However, the response to a given dose was discrepant between both studies. Phase III studies for MS started in December 2007. On May 7, 2013 laquinimod was approved by the Russian Ministry of Health (the FDA analog) as a treatment for relapsing-remitting multiple sclerosis (RRMS) under the brand name Nerventra. The compound has been investigated in two Phase II trials using successive magnetic resonance scans (MRI). Laquinimod seems to be able to reduce the MS disease activity on MRI. In 2011, Teva announced its clinical trials involving laquinimod had failed, being unable to significantly reduce relapses in MS among patients beyond a placebo. It is being investigated as an oral treatment for multiple sclerosis (MS). Laquinimod is an experimental immunomodulator developed by Active Biotech and Teva. However, the final results of above-mentioned phase III trial proved oral laquinimod administered once daily slowed the progression of disability and reduced the rate of relapse in patients with relapsing–remitting multiple sclerosis. Laquinimod is the successor of Active Biotech's failed experimental immunomodulator linomide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Laquinimod is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Laquinimod is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253981
     RDKit          3D
Laquinimod
 42 44  0  0  0  0  0  0  0  0999 V2000
   -3.3329    2.3097   -1.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8780    2.3444   -0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9279    1.2122   -0.2289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949    1.4822   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624    2.6658   -1.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144    0.7432   -0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7745    1.0415   -0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076    1.9700   -1.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9768    0.3622   -0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232    0.6529   -1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876    1.8745   -2.6430 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3104   -0.0045   -1.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3666   -0.9735   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2138   -1.2718    0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0201   -0.6036    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -0.8946    0.9368 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9783   -1.9213    1.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384   -0.2305    0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2009   -0.5966    1.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5294    0.0199    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2623   -0.1091    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8937   -1.2685    1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8326   -2.3890    0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1219   -2.2983   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4877   -1.1423   -0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3516    2.7442   -1.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3844    1.2962   -2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7018    2.2523    0.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3470    3.2994   -0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948    2.6047   -2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2234    0.2158   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2976   -1.5119    0.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2762   -2.0400    1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1556   -2.8884    1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7652   -1.7183    2.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858   -2.0311    2.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    0.7917    1.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4436   -1.2770    2.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366   -3.3236    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -3.2021   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9240   -1.0776   -1.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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M  END


  Mrv1572004021604332D          

 25 27  0  0  0  0            999 V2000
   -0.3562   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3562    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0730   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0730    1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7856    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0730   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0730   -1.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5023   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562   -1.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0730    1.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5023    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5023   -1.4439    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0730    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2149    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2149   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856   -1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5023   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7856    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5023   -1.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  1  1  0  0  0  0
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  9  3  1  0  0  0  0
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 14  5  1  0  0  0  0
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 17  8  1  0  0  0  0
 18 15  2  0  0  0  0
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 25 23  1  0  0  0  0
  6  7  2  0  0  0  0
 19 18  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253981

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(C(=O)C1=C(O)C2=C(C=CC=C2Cl)N(C)C1=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H17ClN2O3/c1-3-22(12-8-5-4-6-9-12)19(25)16-17(23)15-13(20)10-7-11-14(15)21(2)18(16)24/h4-11,23H,3H2,1-2H3

> <INCHI_KEY>
GKWPCEFFIHSJOE-UHFFFAOYSA-N

> <FORMULA>
C19H17ClN2O3

> <MOLECULAR_WEIGHT>
356.81

> <EXACT_MASS>
356.0927701

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.310884082768645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
2.5541251969999994

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.02042797736329

> <JCHEM_PKA_STRONGEST_BASIC>
-2.20630380996822

> <JCHEM_POLAR_SURFACE_AREA>
60.85

> <JCHEM_REFRACTIVITY>
97.30830000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
laquinimod

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253981
     RDKit          3D
Laquinimod
 42 44  0  0  0  0  0  0  0  0999 V2000
   -3.3329    2.3097   -1.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8780    2.3444   -0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9279    1.2122   -0.2289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949    1.4822   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624    2.6658   -1.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144    0.7432   -0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7745    1.0415   -0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076    1.9700   -1.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9768    0.3622   -0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232    0.6529   -1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876    1.8745   -2.6430 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3104   -0.0045   -1.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3666   -0.9735   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2138   -1.2718    0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0201   -0.6036    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -0.8946    0.9368 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9783   -1.9213    1.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384   -0.2305    0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2009   -0.5966    1.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5294    0.0199    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2623   -0.1091    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8937   -1.2685    1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8326   -2.3890    0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1219   -2.2983   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4877   -1.1423   -0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3516    2.7442   -1.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3844    1.2962   -2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6218    2.8908   -2.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018    2.2523    0.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3470    3.2994   -0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2234    0.2158   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1556   -2.8884    1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7652   -1.7183    2.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858   -2.0311    2.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    0.7917    1.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4436   -1.2770    2.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366   -3.3236    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -3.2021   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9240   -1.0776   -1.5652 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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  3 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18  6  1  0
 25 20  1  0
 15  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  8 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 21 38  1  0
 22 39  1  0
 23 40  1  0
 24 41  1  0
 25 42  1  0
M  END

HEADER    PROTEIN                                 02-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-16         0                                  
HETATM    1  C   UNK     0      -0.665  -0.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.665   1.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.003  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.665  -1.155   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.003   1.925   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -3.333  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.333   1.155   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.003  -0.385   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -2.003  -2.695   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.665   1.925   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.671  -1.155   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.665  -2.695   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.333  -1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.003   3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.671   1.925   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0      -4.671  -2.695   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       2.003   1.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.001   1.155   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.001  -0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.333  -2.695   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.671  -0.385   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.333   1.925   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.671  -3.465   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.001  -1.155   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.001  -2.695   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5   10                                                  
CONECT    3    1    6    9                                                  
CONECT    4    1    8   12                                                  
CONECT    5    2    7   14                                                  
CONECT    6    3   11    7                                                  
CONECT    7    5   15    6                                                  
CONECT    8    4   13   17                                                  
CONECT    9    3                                                            
CONECT   10    2                                                            
CONECT   11    6   16   19                                                  
CONECT   12    4                                                            
CONECT   13    8   20   21                                                  
CONECT   14    5                                                            
CONECT   15    7   18                                                       
CONECT   16   11                                                            
CONECT   17    8   22                                                       
CONECT   18   15   19                                                       
CONECT   19   11   18                                                       
CONECT   20   13   23                                                       
CONECT   21   13   24                                                       
CONECT   22   17                                                            
CONECT   23   20   25                                                       
CONECT   24   21   25                                                       
CONECT   25   23   24                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0253981
HETATM    1  C1  UNL     1      -3.333   2.310  -1.817  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.878   2.344  -0.387  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.928   1.212  -0.229  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.595   1.482  -0.479  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.362   2.666  -1.029  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.614   0.743  -0.271  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.774   1.041  -0.983  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.808   1.970  -1.944  1.00  0.00           O  
HETATM    9  C6  UNL     1       2.977   0.362  -0.716  1.00  0.00           C  
HETATM   10  C7  UNL     1       4.123   0.653  -1.415  1.00  0.00           C  
HETATM   11 CL1  UNL     1       4.088   1.875  -2.643  1.00  0.00          CL  
HETATM   12  C8  UNL     1       5.310  -0.005  -1.166  1.00  0.00           C  
HETATM   13  C9  UNL     1       5.367  -0.974  -0.201  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.214  -1.272   0.508  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.020  -0.604   0.250  1.00  0.00           C  
HETATM   16  N2  UNL     1       1.911  -0.895   0.937  1.00  0.00           N  
HETATM   17  C12 UNL     1       1.978  -1.921   1.954  1.00  0.00           C  
HETATM   18  C13 UNL     1       0.738  -0.231   0.676  1.00  0.00           C  
HETATM   19  O3  UNL     1      -0.201  -0.597   1.389  1.00  0.00           O  
HETATM   20  C14 UNL     1      -2.529   0.020   0.159  1.00  0.00           C  
HETATM   21  C15 UNL     1      -3.262  -0.109   1.348  1.00  0.00           C  
HETATM   22  C16 UNL     1      -3.894  -1.269   1.724  1.00  0.00           C  
HETATM   23  C17 UNL     1      -3.833  -2.389   0.926  1.00  0.00           C  
HETATM   24  C18 UNL     1      -3.122  -2.298  -0.247  1.00  0.00           C  
HETATM   25  C19 UNL     1      -2.488  -1.142  -0.630  1.00  0.00           C  
HETATM   26  H1  UNL     1      -4.352   2.744  -1.894  1.00  0.00           H  
HETATM   27  H2  UNL     1      -3.384   1.296  -2.247  1.00  0.00           H  
HETATM   28  H3  UNL     1      -2.622   2.891  -2.461  1.00  0.00           H  
HETATM   29  H4  UNL     1      -3.702   2.252   0.349  1.00  0.00           H  
HETATM   30  H5  UNL     1      -2.347   3.299  -0.182  1.00  0.00           H  
HETATM   31  H6  UNL     1       1.295   2.605  -2.423  1.00  0.00           H  
HETATM   32  H7  UNL     1       6.223   0.216  -1.711  1.00  0.00           H  
HETATM   33  H8  UNL     1       6.298  -1.512   0.018  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.276  -2.040   1.266  1.00  0.00           H  
HETATM   35  H10 UNL     1       2.156  -2.888   1.410  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.765  -1.718   2.709  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.986  -2.031   2.448  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.299   0.792   1.968  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.444  -1.277   2.670  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.337  -3.324   1.220  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.086  -3.202  -0.867  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.924  -1.078  -1.565  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   20
CONECT    4    5    5    6
CONECT    6    7    7   18
CONECT    7    8    9
CONECT    8   31
CONECT    9   10   10   15
CONECT   10   11   12
CONECT   12   13   13   32
CONECT   13   14   33
CONECT   14   15   15   34
CONECT   15   16
CONECT   16   17   18
CONECT   17   35   36   37
CONECT   18   19   19
CONECT   20   21   21   25
CONECT   21   22   38
CONECT   22   23   23   39
CONECT   23   24   40
CONECT   24   25   25   41
CONECT   25   42
END

HMDB0253981
     RDKit          3D
Laquinimod
 42 44  0  0  0  0  0  0  0  0999 V2000
   -3.3329    2.3097   -1.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8780    2.3444   -0.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9279    1.2122   -0.2289 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949    1.4822   -0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3624    2.6658   -1.0289 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144    0.7432   -0.2711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7745    1.0415   -0.9832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8076    1.9700   -1.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9768    0.3622   -0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1232    0.6529   -1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876    1.8745   -2.6430 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3104   -0.0045   -1.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3666   -0.9735   -0.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2138   -1.2718    0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0201   -0.6036    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9106   -0.8946    0.9368 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9783   -1.9213    1.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384   -0.2305    0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2009   -0.5966    1.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5294    0.0199    0.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2623   -0.1091    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8937   -1.2685    1.7238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8326   -2.3890    0.9262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1219   -2.2983   -0.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4877   -1.1423   -0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3516    2.7442   -1.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3844    1.2962   -2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6218    2.8908   -2.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7018    2.2523    0.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3470    3.2994   -0.1822 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2948    2.6047   -2.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2234    0.2158   -1.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2976   -1.5119    0.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2762   -2.0400    1.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1556   -2.8884    1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7652   -1.7183    2.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9858   -2.0311    2.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    0.7917    1.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4436   -1.2770    2.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3366   -3.3236    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863   -3.2021   -0.8667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9240   -1.0776   -1.5652 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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  3 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 18  6  1  0
 25 20  1  0
 15  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  8 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 21 38  1  0
 22 39  1  0
 23 40  1  0
 24 41  1  0
 25 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Laquinimod	MeSH

Chemical Formula

C₁₉H₁₇ClN₂O₃

Average Molecular Weight

356.81

Monoisotopic Molecular Weight

356.0927701

IUPAC Name

5-chloro-N-ethyl-4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide

Traditional Name

laquinimod

CAS Registry Number

Not Available

SMILES

CCN(C(=O)C1=C(O)C2=C(C=CC=C2Cl)N(C)C1=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H17ClN2O3/c1-3-22(12-8-5-4-6-9-12)19(25)16-17(23)15-13(20)10-7-11-14(15)21(2)18(16)24/h4-11,23H,3H2,1-2H3

InChI Key

GKWPCEFFIHSJOE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Aromatic anilides

Alternative Parents

Substituents

Aromatic anilide
Quinoline-3-carboxamide
Haloquinoline
Dihydroquinolone
Hydroxyquinoline
Chloroquinoline
Dihydroquinoline
Quinoline
Pyridine carboxylic acid or derivatives
Hydroxypyridine
Pyridinone
Aryl chloride
Aryl halide
Pyridine
Heteroaromatic compound
Vinylogous amide
Tertiary carboxylic acid amide
Vinylogous acid
Lactam
Carboxamide group
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0253981)

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
logP	2.77	ALOGPS
logP	2.55	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	5.02	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.85 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.31 m³·mol⁻¹	ChemAxon
Polarizability	35.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	186.02	30932474
DeepCCS	[M-H]-	183.662	30932474
DeepCCS	[M-2H]-	217.887	30932474
DeepCCS	[M+Na]+	193.114	30932474
AllCCS	[M+H]+	181.1	32859911
AllCCS	[M+H-H2O]+	178.0	32859911
AllCCS	[M+NH4]+	184.0	32859911
AllCCS	[M+Na]+	184.8	32859911
AllCCS	[M-H]-	182.4	32859911
AllCCS	[M+Na-2H]-	181.8	32859911
AllCCS	[M+HCOO]-	181.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	18.8666 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.39 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3064.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	560.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	211.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	308.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	785.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	818.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	96.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1676.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	614.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1816.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	557.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	521.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	466.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	235.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Laquinimod	CCN(C(=O)C1=C(O)C2=C(C=CC=C2Cl)N(C)C1=O)C1=CC=CC=C1	3884.9	Standard polar	33892256
Laquinimod	CCN(C(=O)C1=C(O)C2=C(C=CC=C2Cl)N(C)C1=O)C1=CC=CC=C1	2831.0	Standard non polar	33892256
Laquinimod	CCN(C(=O)C1=C(O)C2=C(C=CC=C2Cl)N(C)C1=O)C1=CC=CC=C1	2983.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Laquinimod GC-MS (Non-derivatized) - 70eV, Positive	splash10-002u-4769000000-ba48e04fdbcae687b02d	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laquinimod GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laquinimod GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Laquinimod GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	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 - Laquinimod 10V, Positive-QTOF	splash10-0a4i-0019000000-6da9532401f720034532	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laquinimod 20V, Positive-QTOF	splash10-052r-0196000000-6b66e60245cd26bd71df	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laquinimod 40V, Positive-QTOF	splash10-052r-2980000000-d71fda13dfd6db23a46a	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laquinimod 10V, Negative-QTOF	splash10-0a4i-0059000000-a5394a4f4836947e9019	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laquinimod 20V, Negative-QTOF	splash10-0a4i-1395000000-d1da2ec9b5ba36212fd0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laquinimod 40V, Negative-QTOF	splash10-0c00-2910000000-3a625d8bae29b8d0d176	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laquinimod 10V, Positive-QTOF	splash10-0a4r-0059000000-320c8fba478e8dc8a1b2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laquinimod 20V, Positive-QTOF	splash10-000i-0194000000-e98d561a2b084be50b83	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laquinimod 40V, Positive-QTOF	splash10-000i-1390000000-5aba097cf2b15d51f404	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laquinimod 10V, Negative-QTOF	splash10-0a4i-0009000000-f281a2e503abace86d62	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laquinimod 20V, Negative-QTOF	splash10-0a4i-3295000000-9db6a44f01c32b259f4e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laquinimod 40V, Negative-QTOF	splash10-001l-9312000000-35292d9dfbd3df1cdfaf	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB06685

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Laquinimod

METLIN ID

Not Available

PubChem Compound

54677946

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Laquinimod (HMDB0253981)

MOL for HMDB0253981 (Laquinimod)

3D MOL for HMDB0253981 (Laquinimod)

3D SDF for HMDB0253981 (Laquinimod)

3D-SDF for HMDB0253981 (Laquinimod)

PDB for HMDB0253981 (Laquinimod)

3D PDB for HMDB0253981 (Laquinimod)

SMILES for HMDB0253981 (Laquinimod)

INCHI for HMDB0253981 (Laquinimod)

Structure for HMDB0253981 (Laquinimod)

3D Structure for HMDB0253981 (Laquinimod)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra