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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:19:30 UTC

Update Date

2021-09-26 23:01:43 UTC

HMDB ID

HMDB0250320

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cletoquine

Description

Cletoquine, also known as cletochina, belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system. Based on a literature review very few articles have been published on Cletoquine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Cletoquine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Cletoquine 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

HMDB0250320
     RDKit          3D
Cletoquine
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.6163   -2.8172    1.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502   -2.0193    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9837   -1.1763    0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -0.4021   -0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221    0.4658   -0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7157   -0.2491   -0.0566 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8324    0.6224    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2880    1.2806   -1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917    2.0897   -0.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3454   -1.3189   -0.0847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789   -0.3628    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.0686    1.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7880    0.8612    2.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7728    1.4736    1.8516 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0031    1.2182    0.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0321    1.8896   -0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2870    1.6432   -1.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5917    2.4771   -2.1879 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5166    0.7392   -2.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4795    0.0686   -1.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2067    0.2967   -0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278   -3.9297    1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0472   -2.5455    2.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7038   -2.7726    1.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1049   -2.8025   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7973   -1.9300    0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9521   -0.5315    1.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895   -1.1139   -1.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    0.2542   -0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3503    1.2593    0.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6796    0.9297   -1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385   -0.7916    0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447    1.4438    0.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6833    0.0469    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6709    0.5641   -1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5437    1.9868   -1.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9392    1.6684   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -1.5562   -1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -0.5052    2.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    1.0914    3.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6638    2.6109    0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7232    0.5525   -3.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8784   -0.6409   -1.9784 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 11  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 16 41  1  0
 19 42  1  0
 20 43  1  0
M  END

  Mrv1652309112109192D          

 21 22  0  0  0  0            999 V2000
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
 15 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250320

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCCNCCO)NC1=C2C=CC(Cl)=CC2=NC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H22ClN3O/c1-12(3-2-7-18-9-10-21)20-15-6-8-19-16-11-13(17)4-5-14(15)16/h4-6,8,11-12,18,21H,2-3,7,9-10H2,1H3,(H,19,20)

> <INCHI_KEY>
XFICNUNWUREFDP-UHFFFAOYSA-N

> <FORMULA>
C16H22ClN3O

> <MOLECULAR_WEIGHT>
307.82

> <EXACT_MASS>
307.14514

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.29957316027733

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}amino)ethan-1-ol

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
2.1471152826666655

> <ALOGPS_LOGS>
-4.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.602245415945024

> <JCHEM_PKA_STRONGEST_BASIC>
10.001550905933172

> <JCHEM_POLAR_SURFACE_AREA>
57.18

> <JCHEM_REFRACTIVITY>
87.9234

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}amino)ethanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0250320
     RDKit          3D
Cletoquine
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.6163   -2.8172    1.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502   -2.0193    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9837   -1.1763    0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -0.4021   -0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221    0.4658   -0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7157   -0.2491   -0.0566 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8324    0.6224    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2880    1.2806   -1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917    2.0897   -0.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3454   -1.3189   -0.0847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789   -0.3628    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.0686    1.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7880    0.8612    2.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7728    1.4736    1.8516 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0031    1.2182    0.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0321    1.8896   -0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2870    1.6432   -1.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5917    2.4771   -2.1879 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5166    0.7392   -2.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4795    0.0686   -1.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2067    0.2967   -0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278   -3.9297    1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0472   -2.5455    2.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7038   -2.7726    1.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1049   -2.8025   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7973   -1.9300    0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9521   -0.5315    1.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895   -1.1139   -1.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    0.2542   -0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3503    1.2593    0.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6796    0.9297   -1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385   -0.7916    0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447    1.4438    0.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6833    0.0469    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6709    0.5641   -1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5437    1.9868   -1.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9392    1.6684   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -1.5562   -1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -0.5052    2.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    1.0914    3.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6638    2.6109    0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7232    0.5525   -3.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8784   -0.6409   -1.9784 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 11  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 16 41  1  0
 19 42  1  0
 20 43  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.667 -10.780   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335 -10.780   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       4.001 -10.010   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       8.002 -12.320   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       6.668 -13.090   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0      10.669  -7.700   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    2   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   11                                                       
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0250320
HETATM    1  C1  UNL     1      -0.616  -2.817   1.748  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.250  -2.019   0.538  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.984  -1.176   0.754  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.302  -0.402  -0.498  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.522   0.466  -0.363  1.00  0.00           C  
HETATM    6  N1  UNL     1       3.716  -0.249  -0.057  1.00  0.00           N  
HETATM    7  C6  UNL     1       4.832   0.622   0.061  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.288   1.281  -1.191  1.00  0.00           C  
HETATM    9  O1  UNL     1       6.392   2.090  -0.850  1.00  0.00           O  
HETATM   10  N2  UNL     1      -1.345  -1.319  -0.085  1.00  0.00           N  
HETATM   11  C8  UNL     1      -2.179  -0.363   0.539  1.00  0.00           C  
HETATM   12  C9  UNL     1      -1.980  -0.069   1.867  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.788   0.861   2.528  1.00  0.00           C  
HETATM   14  N3  UNL     1      -3.773   1.474   1.852  1.00  0.00           N  
HETATM   15  C11 UNL     1      -4.003   1.218   0.557  1.00  0.00           C  
HETATM   16  C12 UNL     1      -5.032   1.890  -0.060  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.287   1.643  -1.386  1.00  0.00           C  
HETATM   18 CL1  UNL     1      -6.592   2.477  -2.188  1.00  0.00          CL  
HETATM   19  C14 UNL     1      -4.517   0.739  -2.065  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.479   0.069  -1.430  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.207   0.297  -0.110  1.00  0.00           C  
HETATM   22  H1  UNL     1      -0.428  -3.930   1.621  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.047  -2.545   2.672  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.704  -2.773   1.976  1.00  0.00           H  
HETATM   25  H4  UNL     1       0.105  -2.802  -0.220  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.797  -1.930   0.981  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.952  -0.532   1.646  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.389  -1.114  -1.339  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.438   0.254  -0.721  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.350   1.259   0.373  1.00  0.00           H  
HETATM   31  H10 UNL     1       2.680   0.930  -1.381  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.639  -0.792   0.836  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.645   1.444   0.816  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.683   0.047   0.473  1.00  0.00           H  
HETATM   35  H14 UNL     1       5.671   0.564  -1.948  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.544   1.987  -1.627  1.00  0.00           H  
HETATM   37  H16 UNL     1       6.939   1.668  -0.139  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.528  -1.556  -1.108  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.221  -0.505   2.493  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.626   1.091   3.570  1.00  0.00           H  
HETATM   41  H20 UNL     1      -5.664   2.611   0.443  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.723   0.553  -3.102  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.878  -0.641  -1.978  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   10   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   37
CONECT   10   11   38
CONECT   11   12   12   21
CONECT   12   13   39
CONECT   13   14   14   40
CONECT   14   15
CONECT   15   16   16   21
CONECT   16   17   41
CONECT   17   18   19   19
CONECT   19   20   42
CONECT   20   21   21   43
END

HMDB0250320
     RDKit          3D
Cletoquine
 43 44  0  0  0  0  0  0  0  0999 V2000
   -0.6163   -2.8172    1.7475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2502   -2.0193    0.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9837   -1.1763    0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -0.4021   -0.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221    0.4658   -0.3633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7157   -0.2491   -0.0566 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8324    0.6224    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2880    1.2806   -1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917    2.0897   -0.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3454   -1.3189   -0.0847 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1789   -0.3628    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.0686    1.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7880    0.8612    2.5284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7728    1.4736    1.8516 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0031    1.2182    0.5568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0321    1.8896   -0.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2870    1.6432   -1.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5917    2.4771   -2.1879 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.5166    0.7392   -2.0654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4795    0.0686   -1.4300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2067    0.2967   -0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4278   -3.9297    1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0472   -2.5455    2.6721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7038   -2.7726    1.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1049   -2.8025   -0.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7973   -1.9300    0.9812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9521   -0.5315    1.6463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3895   -1.1139   -1.3385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4380    0.2542   -0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3503    1.2593    0.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6796    0.9297   -1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385   -0.7916    0.8361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6447    1.4438    0.8155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6833    0.0469    0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6709    0.5641   -1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5437    1.9868   -1.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9392    1.6684   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5281   -1.5562   -1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2210   -0.5052    2.4927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    1.0914    3.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6638    2.6109    0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7232    0.5525   -3.1015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8784   -0.6409   -1.9784 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 11  1  0
 21 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 16 41  1  0
 19 42  1  0
 20 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Desethylhydroxychloroquine	HMDB
2-((4-((7-Chloro-4-quinolyl)amino)pentyl)amino)ethanol	MeSH
Cletochina	MeSH
Cletoquinum	MeSH

Chemical Formula

C₁₆H₂₂ClN₃O

Average Molecular Weight

307.82

Monoisotopic Molecular Weight

307.14514

IUPAC Name

2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}amino)ethan-1-ol

Traditional Name

2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}amino)ethanol

CAS Registry Number

Not Available

SMILES

CC(CCCNCCO)NC1=C2C=CC(Cl)=CC2=NC=C1

InChI Identifier

InChI=1S/C16H22ClN3O/c1-12(3-2-7-18-9-10-21)20-15-6-8-19-16-11-13(17)4-5-14(15)16/h4-6,8,11-12,18,21H,2-3,7,9-10H2,1H3,(H,19,20)

InChI Key

XFICNUNWUREFDP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Aminoquinolines and derivatives

Direct Parent

4-aminoquinolines

Alternative Parents

Substituents

4-aminoquinoline
Haloquinoline
Chloroquinoline
Aminopyridine
Secondary aliphatic/aromatic amine
Aryl chloride
Aryl halide
Pyridine
Benzenoid
Heteroaromatic compound
1,2-aminoalcohol
Alkanolamine
Secondary aliphatic amine
Azacycle
Secondary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Alcohol
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Primary alcohol
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

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	2.99	ALOGPS
logP	2.15	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	15.6	ChemAxon
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	57.18 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	87.92 m³·mol⁻¹	ChemAxon
Polarizability	34.3 Å³	ChemAxon
Number of Rings	2	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]+	171.236	30932474
DeepCCS	[M-H]-	168.878	30932474
DeepCCS	[M-2H]-	201.764	30932474
DeepCCS	[M+Na]+	177.329	30932474
AllCCS	[M+H]+	172.4	32859911
AllCCS	[M+H-H2O]+	169.4	32859911
AllCCS	[M+NH4]+	175.1	32859911
AllCCS	[M+Na]+	175.9	32859911
AllCCS	[M-H]-	173.3	32859911
AllCCS	[M+Na-2H]-	173.7	32859911
AllCCS	[M+HCOO]-	174.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cletoquine	CC(CCCNCCO)NC1=C2C=CC(Cl)=CC2=NC=C1	3740.8	Standard polar	33892256
Cletoquine	CC(CCCNCCO)NC1=C2C=CC(Cl)=CC2=NC=C1	2813.1	Standard non polar	33892256
Cletoquine	CC(CCCNCCO)NC1=C2C=CC(Cl)=CC2=NC=C1	2883.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cletoquine,2TMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	2808.9	Semi standard non polar	33892256
Cletoquine,2TMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	2731.7	Standard non polar	33892256
Cletoquine,2TMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	3421.9	Standard polar	33892256
Cletoquine,2TMS,isomer #2	CC(CCCNCCO[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2574.1	Semi standard non polar	33892256
Cletoquine,2TMS,isomer #2	CC(CCCNCCO[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2669.4	Standard non polar	33892256
Cletoquine,2TMS,isomer #2	CC(CCCNCCO[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	3213.0	Standard polar	33892256
Cletoquine,2TMS,isomer #3	CC(CCCN(CCO)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2749.1	Semi standard non polar	33892256
Cletoquine,2TMS,isomer #3	CC(CCCN(CCO)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2733.8	Standard non polar	33892256
Cletoquine,2TMS,isomer #3	CC(CCCN(CCO)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	3378.4	Standard polar	33892256
Cletoquine,3TMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2764.5	Semi standard non polar	33892256
Cletoquine,3TMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2761.5	Standard non polar	33892256
Cletoquine,3TMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	3129.4	Standard polar	33892256
Cletoquine,2TBDMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	3255.1	Semi standard non polar	33892256
Cletoquine,2TBDMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	3127.0	Standard non polar	33892256
Cletoquine,2TBDMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	3510.3	Standard polar	33892256
Cletoquine,2TBDMS,isomer #2	CC(CCCNCCO[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3040.6	Semi standard non polar	33892256
Cletoquine,2TBDMS,isomer #2	CC(CCCNCCO[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3080.9	Standard non polar	33892256
Cletoquine,2TBDMS,isomer #2	CC(CCCNCCO[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3337.8	Standard polar	33892256
Cletoquine,2TBDMS,isomer #3	CC(CCCN(CCO)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3223.3	Semi standard non polar	33892256
Cletoquine,2TBDMS,isomer #3	CC(CCCN(CCO)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3137.9	Standard non polar	33892256
Cletoquine,2TBDMS,isomer #3	CC(CCCN(CCO)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3467.2	Standard polar	33892256
Cletoquine,3TBDMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3424.0	Semi standard non polar	33892256
Cletoquine,3TBDMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3276.5	Standard non polar	33892256
Cletoquine,3TBDMS,isomer #1	CC(CCCN(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3337.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cletoquine GC-MS (Non-derivatized) - 70eV, Positive	splash10-055f-9150000000-7e101ec32b7d4d1187ab	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cletoquine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cletoquine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cletoquine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cletoquine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cletoquine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cletoquine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cletoquine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	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 - Cletoquine 10V, Positive-QTOF	splash10-0a4j-0069000000-92dc6716d7cc2a9649e3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cletoquine 20V, Positive-QTOF	splash10-054k-0293000000-251909fdb91536548efd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cletoquine 40V, Positive-QTOF	splash10-004i-3950000000-ef9cf1c30f4b9a13a851	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cletoquine 10V, Negative-QTOF	splash10-0a4i-0019000000-270c91a68c9714bb9140	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cletoquine 20V, Negative-QTOF	splash10-0a4i-1279000000-73457ec28255e20325ad	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cletoquine 40V, Negative-QTOF	splash10-004i-3911000000-a584e5bc5f46c2e887d5	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

64850

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71826

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 Cletoquine (HMDB0250320)

MOL for HMDB0250320 (Cletoquine)

3D MOL for HMDB0250320 (Cletoquine)

3D SDF for HMDB0250320 (Cletoquine)

3D-SDF for HMDB0250320 (Cletoquine)

PDB for HMDB0250320 (Cletoquine)

3D PDB for HMDB0250320 (Cletoquine)

SMILES for HMDB0250320 (Cletoquine)

INCHI for HMDB0250320 (Cletoquine)

Structure for HMDB0250320 (Cletoquine)

3D Structure for HMDB0250320 (Cletoquine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra