Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:45:00 UTC

Update Date

2022-03-07 02:57:13 UTC

HMDB ID

HMDB0041870

Secondary Accession Numbers

HMDB41870

Metabolite Identification

Common Name

Desethylchloroquine

Description

Desethylchloroquine 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 a significant number of articles have been published on Desethylchloroquine.

Structure

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

HMDB0041870
     RDKit          3D
Desethylchloroquine
 42 43  0  0  0  0  0  0  0  0999 V2000
    5.3815   -1.7264    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811   -0.5554   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9076   -0.0860    1.1837 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1776    1.0843    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    1.2587    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5439    1.0829   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788    1.3569   -0.9652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155    2.7856   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8223    0.4233   -0.3415 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608    0.2933   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6138    0.9561   -1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8983    0.8229   -2.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7123    0.0194   -1.6822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3379   -0.6414   -0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2051   -1.4570    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680   -2.1508    1.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0062   -3.1865    2.1263 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5861   -2.0291    1.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6883   -1.2190    1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0317   -0.5195   -0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041   -2.4711    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885   -2.1596   -0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3401   -1.2882    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -1.0607   -0.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8927    0.1801   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6069   -0.8597    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406    1.3005    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7968    1.9771    0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1178    0.5996    1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302    2.3256    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    1.7565   -1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334    0.0231   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017    1.2674   -2.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4827    2.8729    0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9635    3.2525   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7393    3.3581   -0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509   -0.1483    0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592    1.5873   -2.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2143    1.3511   -3.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2171   -1.5475   -0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2627   -2.5525    2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827   -1.1296    1.4710 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 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  2  0
 18 19  1  0
 19 20  2  0
 20 10  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 11 38  1  0
 12 39  1  0
 15 40  1  0
 18 41  1  0
 19 42  1  0
M  END


  Mrv0541 09131211452D          

 20 21  0  0  0  0            999 V2000
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  9  4  1  0  0  0  0
 10  8  2  0  0  0  0
 12  2  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 14  2  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 18  3  1  0  0  0  0
 18  9  1  0  0  0  0
 19 10  1  0  0  0  0
 19 16  2  0  0  0  0
 20 12  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041870

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H22ClN3/c1-3-18-9-4-5-12(2)20-15-8-10-19-16-11-13(17)6-7-14(15)16/h6-8,10-12,18H,3-5,9H2,1-2H3,(H,19,20)

> <INCHI_KEY>
MCYUUUTUAAGOOT-UHFFFAOYSA-N

> <FORMULA>
C16H22ClN3

> <MOLECULAR_WEIGHT>
291.819

> <EXACT_MASS>
291.150225426

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.494570402646865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-N-[5-(ethylamino)pentan-2-yl]quinolin-4-amine

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
3.1940252493333325

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
10.620879562512721

> <JCHEM_POLAR_SURFACE_AREA>
36.95

> <JCHEM_REFRACTIVITY>
86.3797

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-chloro-N-[5-(ethylamino)pentan-2-yl]quinolin-4-amine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0041870
     RDKit          3D
Desethylchloroquine
 42 43  0  0  0  0  0  0  0  0999 V2000
    5.3815   -1.7264    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811   -0.5554   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9076   -0.0860    1.1837 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1776    1.0843    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    1.2587    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5439    1.0829   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788    1.3569   -0.9652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155    2.7856   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8223    0.4233   -0.3415 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608    0.2933   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6138    0.9561   -1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8983    0.8229   -2.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7123    0.0194   -1.6822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3379   -0.6414   -0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2051   -1.4570    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680   -2.1508    1.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0062   -3.1865    2.1263 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5861   -2.0291    1.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6883   -1.2190    1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0317   -0.5195   -0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041   -2.4711    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885   -2.1596   -0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3401   -1.2882    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -1.0607   -0.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8927    0.1801   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6069   -0.8597    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406    1.3005    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7968    1.9771    0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1178    0.5996    1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302    2.3256    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    1.7565   -1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334    0.0231   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017    1.2674   -2.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4827    2.8729    0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9635    3.2525   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7393    3.3581   -0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509   -0.1483    0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592    1.5873   -2.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2143    1.3511   -3.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2171   -1.5475   -0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2627   -2.5525    2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827   -1.1296    1.4710 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 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  2  0
 18 19  1  0
 19 20  2  0
 20 10  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 11 38  1  0
 12 39  1  0
 15 40  1  0
 18 41  1  0
 19 42  1  0
M  END

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       5.335   4.620   0.000  0.00  0.00          Cl+0
HETATM   18  N   UNK     0      -8.002   1.540   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
CONECT    1    3                                                            
CONECT    2   12                                                            
CONECT    3    1   18                                                       
CONECT    4    5    9                                                       
CONECT    5    4   12                                                       
CONECT    6    7   13                                                       
CONECT    7    6   14                                                       
CONECT    8   10   15                                                       
CONECT    9    4   18                                                       
CONECT   10    8   19                                                       
CONECT   11   13   16                                                       
CONECT   12    2    5   20                                                  
CONECT   13    6   11   17                                                  
CONECT   14    7   15   16                                                  
CONECT   15    8   14   20                                                  
CONECT   16   11   14   19                                                  
CONECT   17   13                                                            
CONECT   18    3    9                                                       
CONECT   19   10   16                                                       
CONECT   20   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0041870
HETATM    1  C1  UNL     1       5.381  -1.726   0.149  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.381  -0.555  -0.055  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.908  -0.086   1.184  1.00  0.00           N  
HETATM    4  C3  UNL     1       3.178   1.084   1.322  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.786   1.259   0.864  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.544   1.083  -0.593  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.079   1.357  -0.965  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.216   2.786  -0.568  1.00  0.00           C  
HETATM    9  N2  UNL     1      -0.822   0.423  -0.342  1.00  0.00           N  
HETATM   10  C8  UNL     1      -2.161   0.293  -0.762  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.614   0.956  -1.913  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.898   0.823  -2.381  1.00  0.00           C  
HETATM   13  N3  UNL     1      -4.712   0.019  -1.682  1.00  0.00           N  
HETATM   14  C11 UNL     1      -4.338  -0.641  -0.573  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.205  -1.457   0.122  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.868  -2.151   1.266  1.00  0.00           C  
HETATM   17 CL1  UNL     1      -6.006  -3.187   2.126  1.00  0.00          CL  
HETATM   18  C14 UNL     1      -3.586  -2.029   1.752  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.688  -1.219   1.078  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.032  -0.520  -0.075  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.004  -2.471   0.851  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.588  -2.160  -0.833  1.00  0.00           H  
HETATM   23  H3  UNL     1       6.340  -1.288   0.535  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.577  -1.061  -0.639  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.893   0.180  -0.680  1.00  0.00           H  
HETATM   26  H6  UNL     1       3.607  -0.860   1.840  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.141   1.300   2.460  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.797   1.977   0.946  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.118   0.600   1.488  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.430   2.326   1.123  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.154   1.756  -1.219  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.733   0.023  -0.861  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.002   1.267  -2.055  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.483   2.873   0.503  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.963   3.252  -1.195  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.739   3.358  -0.720  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.451  -0.148   0.425  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.959   1.587  -2.482  1.00  0.00           H  
HETATM   39  H19 UNL     1      -4.214   1.351  -3.278  1.00  0.00           H  
HETATM   40  H20 UNL     1      -6.217  -1.548  -0.277  1.00  0.00           H  
HETATM   41  H21 UNL     1      -3.263  -2.552   2.644  1.00  0.00           H  
HETATM   42  H22 UNL     1      -1.683  -1.130   1.471  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8    9   33
CONECT    8   34   35   36
CONECT    9   10   37
CONECT   10   11   11   20
CONECT   11   12   38
CONECT   12   13   13   39
CONECT   13   14
CONECT   14   15   15   20
CONECT   15   16   40
CONECT   16   17   18   18
CONECT   18   19   41
CONECT   19   20   20   42
END

HMDB0041870
     RDKit          3D
Desethylchloroquine
 42 43  0  0  0  0  0  0  0  0999 V2000
    5.3815   -1.7264    0.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811   -0.5554   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9076   -0.0860    1.1837 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1776    1.0843    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    1.2587    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5439    1.0829   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788    1.3569   -0.9652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155    2.7856   -0.5677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8223    0.4233   -0.3415 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608    0.2933   -0.7623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6138    0.9561   -1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8983    0.8229   -2.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7123    0.0194   -1.6822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3379   -0.6414   -0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2051   -1.4570    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8680   -2.1508    1.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0062   -3.1865    2.1263 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5861   -2.0291    1.7519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6883   -1.2190    1.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0317   -0.5195   -0.0747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0041   -2.4711    0.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5885   -2.1596   -0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3401   -1.2882    0.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -1.0607   -0.6389 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8927    0.1801   -0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6069   -0.8597    1.8400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1406    1.3005    2.4601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7968    1.9771    0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1178    0.5996    1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302    2.3256    1.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    1.7565   -1.2189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334    0.0231   -0.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017    1.2674   -2.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4827    2.8729    0.5035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9635    3.2525   -1.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7393    3.3581   -0.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4509   -0.1483    0.4248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592    1.5873   -2.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2143    1.3511   -3.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2171   -1.5475   -0.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2627   -2.5525    2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6827   -1.1296    1.4710 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
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 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  2  0
 18 19  1  0
 19 20  2  0
 20 10  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 11 38  1  0
 12 39  1  0
 15 40  1  0
 18 41  1  0
 19 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Desethyl chloroquine	HMDB
Chloroquine m (des-ethyl)	HMDB
N4-(7-Chloro-4-quinolinyl)-N1-ethyl-1,4-pentanediamine	HMDB
Deethylchloroquine	HMDB
Desethylchloroquine dihydrochloride	HMDB
Desethylchloroquine hydrochloride	HMDB
Desethylchloroquine oxalate (1:2)	HMDB
Monodesethylchloroquine	HMDB
Desethylchloroquine	MeSH

Chemical Formula

C₁₆H₂₂ClN₃

Average Molecular Weight

291.819

Monoisotopic Molecular Weight

291.150225426

IUPAC Name

7-chloro-N-[5-(ethylamino)pentan-2-yl]quinolin-4-amine

Traditional Name

7-chloro-N-[5-(ethylamino)pentan-2-yl]quinolin-4-amine

CAS Registry Number

1476-52-4

SMILES

CCNCCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1

InChI Identifier

InChI=1S/C16H22ClN3/c1-3-18-9-4-5-12(2)20-15-8-10-19-16-11-13(17)6-7-14(15)16/h6-8,10-12,18H,3-5,9H2,1-2H3,(H,19,20)

InChI Key

MCYUUUTUAAGOOT-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 aliphatic amine
Secondary amine
Amine
Organonitrogen compound
Organochloride
Organohalogen compound
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

Cellular substructure

Membrane (HMDB: HMDB0041870)

Source

Exogenous

Exogenous (HMDB: HMDB0041870)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	3.96	ALOGPS
logP	3.19	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	10.62	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	36.95 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	86.38 m³·mol⁻¹	ChemAxon
Polarizability	33.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	172.587	30932474
DeepCCS	[M-H]-	170.229	30932474
DeepCCS	[M-2H]-	203.115	30932474
DeepCCS	[M+Na]+	178.68	30932474
AllCCS	[M+H]+	170.2	32859911
AllCCS	[M+H-H2O]+	167.0	32859911
AllCCS	[M+NH4]+	173.2	32859911
AllCCS	[M+Na]+	174.1	32859911
AllCCS	[M-H]-	173.0	32859911
AllCCS	[M+Na-2H]-	173.4	32859911
AllCCS	[M+HCOO]-	173.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.2 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1796 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.21 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	228.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1206.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	198.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	112.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	327.1 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	306.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	515.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	669.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	87.7 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	678.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	178.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	498.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	398.1 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	40.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Desethylchloroquine	CCNCCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1	3429.0	Standard polar	33892256
Desethylchloroquine	CCNCCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1	2587.0	Standard non polar	33892256
Desethylchloroquine	CCNCCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1	2595.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Desethylchloroquine,1TMS,isomer #1	CCN(CCCC(C)NC1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2623.5	Semi standard non polar	33892256
Desethylchloroquine,1TMS,isomer #1	CCN(CCCC(C)NC1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2509.2	Standard non polar	33892256
Desethylchloroquine,1TMS,isomer #2	CCNCCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2389.5	Semi standard non polar	33892256
Desethylchloroquine,1TMS,isomer #2	CCNCCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2483.7	Standard non polar	33892256
Desethylchloroquine,2TMS,isomer #1	CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C)[Si](C)(C)C	2558.4	Semi standard non polar	33892256
Desethylchloroquine,2TMS,isomer #1	CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C)[Si](C)(C)C	2608.5	Standard non polar	33892256
Desethylchloroquine,1TBDMS,isomer #1	CCN(CCCC(C)NC1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2829.0	Semi standard non polar	33892256
Desethylchloroquine,1TBDMS,isomer #1	CCN(CCCC(C)NC1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2725.3	Standard non polar	33892256
Desethylchloroquine,1TBDMS,isomer #2	CCNCCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2610.4	Semi standard non polar	33892256
Desethylchloroquine,1TBDMS,isomer #2	CCNCCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2712.9	Standard non polar	33892256
Desethylchloroquine,2TBDMS,isomer #1	CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3019.8	Semi standard non polar	33892256
Desethylchloroquine,2TBDMS,isomer #1	CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3022.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Desethylchloroquine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4090000000-3879be297fda50cde013	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desethylchloroquine 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 - Desethylchloroquine 10V, Positive-QTOF	splash10-0006-0090000000-7c64baaac576471d18ce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethylchloroquine 20V, Positive-QTOF	splash10-00mn-5390000000-fd8d91933968198e8c6b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethylchloroquine 40V, Positive-QTOF	splash10-056u-9330000000-58165c6c781995b726a1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethylchloroquine 10V, Negative-QTOF	splash10-0006-0090000000-f122e3d86f59f798f533	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethylchloroquine 20V, Negative-QTOF	splash10-0006-1190000000-1c4f708b4bb2710c8834	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethylchloroquine 40V, Negative-QTOF	splash10-002f-9530000000-cab937cd113276e8e69b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethylchloroquine 10V, Negative-QTOF	splash10-0006-0290000000-9b49adc17ce7947c92d5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethylchloroquine 20V, Negative-QTOF	splash10-0006-0290000000-184156387174893a4aea	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethylchloroquine 40V, Negative-QTOF	splash10-004i-2920000000-2f8c174cd942e44f6544	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethylchloroquine 10V, Positive-QTOF	splash10-0006-0090000000-b60dba4d0aae1b30835c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethylchloroquine 20V, Positive-QTOF	splash10-0005-0090000000-7108a75cf5babbba2460	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desethylchloroquine 40V, Positive-QTOF	splash10-004i-6950000000-c0dbbb8a3642435ae351	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

86173

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

95478

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

Not Available

Showing metabocard for Desethylchloroquine (HMDB0041870)

MOL for HMDB0041870 (Desethylchloroquine)

3D MOL for HMDB0041870 (Desethylchloroquine)

3D SDF for HMDB0041870 (Desethylchloroquine)

3D-SDF for HMDB0041870 (Desethylchloroquine)

PDB for HMDB0041870 (Desethylchloroquine)

3D PDB for HMDB0041870 (Desethylchloroquine)

SMILES for HMDB0041870 (Desethylchloroquine)

INCHI for HMDB0041870 (Desethylchloroquine)

Structure for HMDB0041870 (Desethylchloroquine)

3D Structure for HMDB0041870 (Desethylchloroquine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra