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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:46:21 UTC

Update Date

2021-09-26 23:00:00 UTC

HMDB ID

HMDB0249267

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Didesethyl Chloroquine

Description

Didesethyl Chloroquine, also known as CQMM, 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 Didesethyl Chloroquine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Didesethyl chloroquine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Didesethyl Chloroquine 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

HMDB0249267
     RDKit          3D
Didesethyl Chloroquine
 36 37  0  0  0  0  0  0  0  0999 V2000
   -0.8727   -2.3995    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9103   -1.0838    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2866   -0.4941    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870   -0.2461   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3541    0.3462   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    1.5917    0.6619 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110   -0.1334    0.1968 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103   -0.3522    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709   -1.4518    0.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3421   -1.6765    0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1361   -0.8020    0.2546 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6683    0.2750   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5332    1.1353   -1.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0868    2.2501   -1.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025    3.3318   -2.4617 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    2.5083   -1.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8583    1.6243   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914    0.5057   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -3.2110    0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -2.4464   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8523   -2.5868   -0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5187   -1.2222    1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250    0.4788    1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9137   -1.1488    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250   -1.1280   -0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    0.5095   -0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9485   -0.3925    0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9101    0.5270   -0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9893    1.4899    1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2352    2.0048    0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4098    0.6998   -0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097   -2.1280    1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402   -2.5416    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042    0.9355   -0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434    3.3731   -2.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016    1.8579   -1.1489 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
  2  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18  8  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 13 34  1  0
 16 35  1  0
 17 36  1  0
M  END


  Mrv1652309112105462D          

 18 19  0  0  0  0            999 V2000
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    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
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  8 17  1  0  0  0  0
 12 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249267

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H18ClN3/c1-10(3-2-7-16)18-13-6-8-17-14-9-11(15)4-5-12(13)14/h4-6,8-10H,2-3,7,16H2,1H3,(H,17,18)

> <INCHI_KEY>
GYEDIFVVTRKXHP-UHFFFAOYSA-N

> <FORMULA>
C14H18ClN3

> <MOLECULAR_WEIGHT>
263.77

> <EXACT_MASS>
263.1189253

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.16926224809312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N4-(7-chloroquinolin-4-yl)pentane-1,4-diamine

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
2.4046369010000004

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
10.204288724755303

> <JCHEM_POLAR_SURFACE_AREA>
50.94

> <JCHEM_REFRACTIVITY>
76.8565

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N4-(7-chloroquinolin-4-yl)pentane-1,4-diamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249267
     RDKit          3D
Didesethyl Chloroquine
 36 37  0  0  0  0  0  0  0  0999 V2000
   -0.8727   -2.3995    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9103   -1.0838    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2866   -0.4941    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870   -0.2461   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3541    0.3462   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    1.5917    0.6619 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110   -0.1334    0.1968 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103   -0.3522    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709   -1.4518    0.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3421   -1.6765    0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1361   -0.8020    0.2546 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6683    0.2750   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5332    1.1353   -1.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0868    2.2501   -1.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025    3.3318   -2.4617 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    2.5083   -1.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8583    1.6243   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914    0.5057   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -3.2110    0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -2.4464   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8523   -2.5868   -0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5187   -1.2222    1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250    0.4788    1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9137   -1.1488    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250   -1.1280   -0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    0.5095   -0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9485   -0.3925    0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9101    0.5270   -0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9893    1.4899    1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2352    2.0048    0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4098    0.6998   -0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097   -2.1280    1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402   -2.5416    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042    0.9355   -0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434    3.3731   -2.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016    1.8579   -1.1489 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
  2  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18  8  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 13 34  1  0
 16 35  1  0
 17 36  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       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -4.001  -8.470   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       2.667  -7.700   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       6.668 -10.010   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       9.336  -5.390   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8                                                       
CONECT   18   12                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0249267
HETATM    1  C1  UNL     1      -0.873  -2.400   0.125  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.910  -1.084   0.815  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.287  -0.494   0.963  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.987  -0.246  -0.338  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.354   0.346  -0.053  1.00  0.00           C  
HETATM    6  N1  UNL     1      -4.276   1.592   0.662  1.00  0.00           N  
HETATM    7  N2  UNL     1       0.011  -0.133   0.197  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.410  -0.352   0.203  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.971  -1.452   0.853  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.342  -1.677   0.877  1.00  0.00           C  
HETATM   11  N3  UNL     1       4.136  -0.802   0.255  1.00  0.00           N  
HETATM   12  C9  UNL     1       3.668   0.275  -0.389  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.533   1.135  -1.009  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.087   2.250  -1.679  1.00  0.00           C  
HETATM   15 CL1  UNL     1       5.203   3.332  -2.462  1.00  0.00          CL  
HETATM   16  C12 UNL     1       2.738   2.508  -1.727  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.858   1.624  -1.090  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.291   0.506  -0.417  1.00  0.00           C  
HETATM   19  H1  UNL     1      -0.752  -3.211   0.859  1.00  0.00           H  
HETATM   20  H2  UNL     1      -0.032  -2.446  -0.596  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.852  -2.587  -0.368  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.519  -1.222   1.852  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.225   0.479   1.490  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.914  -1.149   1.597  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.125  -1.128  -0.976  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.451   0.510  -0.958  1.00  0.00           H  
HETATM   27  H9  UNL     1      -4.948  -0.392   0.522  1.00  0.00           H  
HETATM   28  H10 UNL     1      -4.910   0.527  -0.996  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.989   1.490   1.659  1.00  0.00           H  
HETATM   30  H12 UNL     1      -5.235   2.005   0.666  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.410   0.700  -0.239  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.310  -2.128   1.345  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.740  -2.542   1.392  1.00  0.00           H  
HETATM   34  H16 UNL     1       5.604   0.935  -0.974  1.00  0.00           H  
HETATM   35  H17 UNL     1       2.343   3.373  -2.243  1.00  0.00           H  
HETATM   36  H18 UNL     1       0.802   1.858  -1.149  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    7   22
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6   27   28
CONECT    6   29   30
CONECT    7    8   31
CONECT    8    9    9   18
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   12
CONECT   12   13   13   18
CONECT   13   14   34
CONECT   14   15   16   16
CONECT   16   17   35
CONECT   17   18   18   36
END

HMDB0249267
     RDKit          3D
Didesethyl Chloroquine
 36 37  0  0  0  0  0  0  0  0999 V2000
   -0.8727   -2.3995    0.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9103   -1.0838    0.8148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2866   -0.4941    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9870   -0.2461   -0.3383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3541    0.3462   -0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756    1.5917    0.6619 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0110   -0.1334    0.1968 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4103   -0.3522    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709   -1.4518    0.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3421   -1.6765    0.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1361   -0.8020    0.2546 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6683    0.2750   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5332    1.1353   -1.0092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0868    2.2501   -1.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025    3.3318   -2.4617 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7383    2.5083   -1.7272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8583    1.6243   -1.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914    0.5057   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7521   -3.2110    0.8591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -2.4464   -0.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8523   -2.5868   -0.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5187   -1.2222    1.8521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2250    0.4788    1.4902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9137   -1.1488    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250   -1.1280   -0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4505    0.5095   -0.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9485   -0.3925    0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9101    0.5270   -0.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9893    1.4899    1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2352    2.0048    0.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4098    0.6998   -0.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097   -2.1280    1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402   -2.5416    1.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042    0.9355   -0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3434    3.3731   -2.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8016    1.8579   -1.1489 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
  2  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18  8  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 13 34  1  0
 16 35  1  0
 17 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
CQMM	MeSH
N,N-Dideethylchloroquine	MeSH
N,N-Dideethylchloroquine sulfate	MeSH
Bi(deethyl)chloroquine	MeSH
Bisdeethylchloroquine	MeSH
Bisdesethylchloroquine	MeSH
Didesethylchloroquine	MeSH

Chemical Formula

C₁₄H₁₈ClN₃

Average Molecular Weight

263.77

Monoisotopic Molecular Weight

263.1189253

IUPAC Name

N4-(7-chloroquinolin-4-yl)pentane-1,4-diamine

Traditional Name

N4-(7-chloroquinolin-4-yl)pentane-1,4-diamine

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C14H18ClN3/c1-10(3-2-7-16)18-13-6-8-17-14-9-11(15)4-5-12(13)14/h4-6,8-10H,2-3,7,16H2,1H3,(H,17,18)

InChI Key

GYEDIFVVTRKXHP-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
Azacycle
Secondary amine
Amine
Primary amine
Organonitrogen compound
Organochloride
Organohalogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen 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)

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	3.52	ALOGPS
logP	2.4	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.94 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	76.86 m³·mol⁻¹	ChemAxon
Polarizability	29.17 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]+	159.977	30932474
DeepCCS	[M-H]-	157.619	30932474
DeepCCS	[M-2H]-	190.505	30932474
DeepCCS	[M+Na]+	166.07	30932474
AllCCS	[M+H]+	161.5	32859911
AllCCS	[M+H-H2O]+	158.0	32859911
AllCCS	[M+NH4]+	164.8	32859911
AllCCS	[M+Na]+	165.7	32859911
AllCCS	[M-H]-	164.3	32859911
AllCCS	[M+Na-2H]-	164.6	32859911
AllCCS	[M+HCOO]-	165.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Didesethyl Chloroquine	CC(CCCN)NC1=C2C=CC(Cl)=CC2=NC=C1	3295.0	Standard polar	33892256
Didesethyl Chloroquine	CC(CCCN)NC1=C2C=CC(Cl)=CC2=NC=C1	2494.3	Standard non polar	33892256
Didesethyl Chloroquine	CC(CCCN)NC1=C2C=CC(Cl)=CC2=NC=C1	2480.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Didesethyl Chloroquine,1TMS,isomer #1	CC(CCCN[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	2490.9	Semi standard non polar	33892256
Didesethyl Chloroquine,1TMS,isomer #1	CC(CCCN[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	2367.8	Standard non polar	33892256
Didesethyl Chloroquine,1TMS,isomer #1	CC(CCCN[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	3227.5	Standard polar	33892256
Didesethyl Chloroquine,1TMS,isomer #2	CC(CCCN)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2330.3	Semi standard non polar	33892256
Didesethyl Chloroquine,1TMS,isomer #2	CC(CCCN)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2395.8	Standard non polar	33892256
Didesethyl Chloroquine,1TMS,isomer #2	CC(CCCN)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	3308.9	Standard polar	33892256
Didesethyl Chloroquine,2TMS,isomer #1	CC(CCCN([Si](C)(C)C)[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	2630.9	Semi standard non polar	33892256
Didesethyl Chloroquine,2TMS,isomer #1	CC(CCCN([Si](C)(C)C)[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	2608.8	Standard non polar	33892256
Didesethyl Chloroquine,2TMS,isomer #1	CC(CCCN([Si](C)(C)C)[Si](C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	3089.9	Standard polar	33892256
Didesethyl Chloroquine,2TMS,isomer #2	CC(CCCN[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2390.0	Semi standard non polar	33892256
Didesethyl Chloroquine,2TMS,isomer #2	CC(CCCN[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2493.9	Standard non polar	33892256
Didesethyl Chloroquine,2TMS,isomer #2	CC(CCCN[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2895.3	Standard polar	33892256
Didesethyl Chloroquine,3TMS,isomer #1	CC(CCCN([Si](C)(C)C)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2616.7	Semi standard non polar	33892256
Didesethyl Chloroquine,3TMS,isomer #1	CC(CCCN([Si](C)(C)C)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2666.8	Standard non polar	33892256
Didesethyl Chloroquine,3TMS,isomer #1	CC(CCCN([Si](C)(C)C)[Si](C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2812.5	Standard polar	33892256
Didesethyl Chloroquine,1TBDMS,isomer #1	CC(CCCN[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	2702.8	Semi standard non polar	33892256
Didesethyl Chloroquine,1TBDMS,isomer #1	CC(CCCN[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	2579.9	Standard non polar	33892256
Didesethyl Chloroquine,1TBDMS,isomer #1	CC(CCCN[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	3257.1	Standard polar	33892256
Didesethyl Chloroquine,1TBDMS,isomer #2	CC(CCCN)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2560.6	Semi standard non polar	33892256
Didesethyl Chloroquine,1TBDMS,isomer #2	CC(CCCN)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2616.3	Standard non polar	33892256
Didesethyl Chloroquine,1TBDMS,isomer #2	CC(CCCN)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3330.2	Standard polar	33892256
Didesethyl Chloroquine,2TBDMS,isomer #1	CC(CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	3068.0	Semi standard non polar	33892256
Didesethyl Chloroquine,2TBDMS,isomer #1	CC(CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	2957.5	Standard non polar	33892256
Didesethyl Chloroquine,2TBDMS,isomer #1	CC(CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)NC1=CC=NC2=CC(Cl)=CC=C12	3159.8	Standard polar	33892256
Didesethyl Chloroquine,2TBDMS,isomer #2	CC(CCCN[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2837.9	Semi standard non polar	33892256
Didesethyl Chloroquine,2TBDMS,isomer #2	CC(CCCN[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2917.2	Standard non polar	33892256
Didesethyl Chloroquine,2TBDMS,isomer #2	CC(CCCN[Si](C)(C)C(C)(C)C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3048.7	Standard polar	33892256
Didesethyl Chloroquine,3TBDMS,isomer #1	CC(CCCN([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	3266.0	Semi standard non polar	33892256
Didesethyl Chloroquine,3TBDMS,isomer #1	CC(CCCN([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	3182.7	Standard non polar	33892256
Didesethyl Chloroquine,3TBDMS,isomer #1	CC(CCCN([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	3036.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Didesethyl Chloroquine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9140000000-043ce222df186feded66	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Didesethyl Chloroquine 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 - Didesethyl Chloroquine 10V, Positive-QTOF	splash10-03di-0090000000-efa7b3b98a3eb9a5fae6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesethyl Chloroquine 20V, Positive-QTOF	splash10-0002-0190000000-95756c1a840d6a8456f3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesethyl Chloroquine 40V, Positive-QTOF	splash10-004i-2930000000-6fcf0fed654eba1aa598	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesethyl Chloroquine 10V, Negative-QTOF	splash10-03fr-0590000000-93e690ffc3e38a3bf746	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesethyl Chloroquine 20V, Negative-QTOF	splash10-03di-0590000000-deab124fe759f43b1395	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Didesethyl Chloroquine 40V, Negative-QTOF	splash10-0059-4910000000-d6ad74cdd8a8f22bbc2a	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

109371

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122672

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 Didesethyl Chloroquine (HMDB0249267)

MOL for HMDB0249267 (Didesethyl Chloroquine)

3D MOL for HMDB0249267 (Didesethyl Chloroquine)

3D SDF for HMDB0249267 (Didesethyl Chloroquine)

3D-SDF for HMDB0249267 (Didesethyl Chloroquine)

PDB for HMDB0249267 (Didesethyl Chloroquine)

3D PDB for HMDB0249267 (Didesethyl Chloroquine)

SMILES for HMDB0249267 (Didesethyl Chloroquine)

INCHI for HMDB0249267 (Didesethyl Chloroquine)

Structure for HMDB0249267 (Didesethyl Chloroquine)

3D Structure for HMDB0249267 (Didesethyl Chloroquine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra