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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8)transporters (1) Show 9 proteins XML

enzymes (8)transporters (1) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:43 UTC

HMDB ID

HMDB0014746

Secondary Accession Numbers

HMDB14746

Metabolite Identification

Common Name

Chloroquine

Description

Chloroquine is only found in individuals that have used or taken this drug. It is a prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses. [PubChem]The mechanism of plasmodicidal action of chloroquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites. nside red blood cells, the malarial parasite must degrade hemoglobin to acquire essential amino acids, which the parasite requires to construct its own protein and for energy metabolism. Digestion is carried out in a vacuole of the parasite cell.During this process, the parasite produces the toxic and soluble molecule heme. The heme moiety consists of a porphyrin ring called Fe(II)-protoporphyrin IX (FP). To avoid destruction by this molecule, the parasite biocrystallizes heme to form hemozoin, a non-toxic molecule. Hemozoin collects in the digestive vacuole as insoluble crystals.Chloroquine enters the red blood cell, inhabiting parasite cell, and digestive vacuole by simple diffusion. Chloroquine then becomes protonated (to CQ2+), as the digestive vacuole is known to be acidic (pH 4.7); chloroquine then cannot leave by diffusion. Chloroquine caps hemozoin molecules to prevent further biocrystallization of heme, thus leading to heme buildup. Chloroquine binds to heme (or FP) to form what is known as the FP-Chloroquine complex; this complex is highly toxic to the cell and disrupts membrane function. Action of the toxic FP-Chloroquine and FP results in cell lysis and ultimately parasite cell autodigestion. In essence, the parasite cell drowns in its own metabolic products.

Structure

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

HMDB0014746
     RDKit          3D
Chloroquine
 48 49  0  0  0  0  0  0  0  0999 V2000
   -3.3094   -1.5712   -1.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9510   -0.0947   -1.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    0.5721   -0.4469 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6155    0.7362   -0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3680   -0.5011    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5285    1.7532   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    1.6135    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    0.7278    1.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635    0.5735    1.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518   -0.3123    2.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5469    0.3514    0.6154 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107   -0.5639    0.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190   -1.7739    1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7777   -2.6241    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7118   -2.3123   -0.1270 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6521   -1.1333   -0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6607   -0.8463   -1.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5847    0.3687   -2.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8151    0.8325   -3.4834 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5849    1.2727   -2.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    0.9318   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6215   -0.2620   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8730   -2.1017   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3747   -1.7747   -1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7783   -2.0031   -2.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -0.0664   -1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    0.3299   -2.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1639    1.3743   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6256    1.3883    0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7582   -1.3657    0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0439   -0.3314    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1127   -0.6941   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800    2.1989    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6842    2.5339   -0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082    2.6418    0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4697    1.3826   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2452   -0.2838    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    1.2083    2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8895    1.6559    2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -0.4682    3.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277    0.2173    3.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1975   -1.2575    2.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3723    0.9700   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9803   -2.0983    1.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8034   -3.5863    1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4692   -1.5079   -1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177    2.2212   -2.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8367    1.6782   -0.9533 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
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 16 17  2  0
 17 18  1  0
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 18 20  2  0
 20 21  1  0
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 22 12  1  0
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  1 23  1  0
  1 24  1  0
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  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 14 45  1  0
 17 46  1  0
 20 47  1  0
 21 48  1  0
M  END

608
  Mrv0541 02231214482D          

 22 23  0  0  1  0            999 V2000
    8.1347    3.3056    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.0768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    0.8107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    3.2857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -1.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    2.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644   -3.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    2.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    1.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    3.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    2.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    2.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 22  1  0  0  0  0
  2  8  1  0  0  0  0
  2 10  1  0  0  0  0
  2 11  1  0  0  0  0
  3  7  1  0  0  0  0
  3 12  1  0  0  0  0
  4 17  2  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 13  2  0  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 16 19  2  0  0  0  0
 17 20  1  0  0  0  0
 18 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014746

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)

> <INCHI_KEY>
WHTVZRBIWZFKQO-UHFFFAOYSA-N

> <FORMULA>
C18H26ClN3

> <MOLECULAR_WEIGHT>
319.872

> <EXACT_MASS>
319.181525554

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.28790341691832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.28

> <JCHEM_LOGP>
3.933881141333334

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
10.324447273782475

> <JCHEM_POLAR_SURFACE_AREA>
28.16

> <JCHEM_REFRACTIVITY>
96.42300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.75e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014746
     RDKit          3D
Chloroquine
 48 49  0  0  0  0  0  0  0  0999 V2000
   -3.3094   -1.5712   -1.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9510   -0.0947   -1.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    0.5721   -0.4469 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6155    0.7362   -0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3680   -0.5011    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5285    1.7532   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    1.6135    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    0.7278    1.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635    0.5735    1.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518   -0.3123    2.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5469    0.3514    0.6154 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107   -0.5639    0.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190   -1.7739    1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7777   -2.6241    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7118   -2.3123   -0.1270 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6521   -1.1333   -0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6607   -0.8463   -1.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5847    0.3687   -2.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8151    0.8325   -3.4834 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5849    1.2727   -2.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    0.9318   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6215   -0.2620   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8730   -2.1017   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3747   -1.7747   -1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7783   -2.0031   -2.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -0.0664   -1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    0.3299   -2.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1639    1.3743   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6256    1.3883    0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7582   -1.3657    0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0439   -0.3314    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1127   -0.6941   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800    2.1989    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6842    2.5339   -0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082    2.6418    0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4697    1.3826   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2452   -0.2838    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    1.2083    2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8895    1.6559    2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -0.4682    3.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277    0.2173    3.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1975   -1.2575    2.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3723    0.9700   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9803   -2.0983    1.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8034   -3.5863    1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4692   -1.5079   -1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177    2.2212   -2.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8367    1.6782   -0.9533 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 12  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 14 45  1  0
 17 46  1  0
 20 47  1  0
 21 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 608                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      15.185   6.170   0.000  0.00  0.00          Cl+0
HETATM    2  N   UNK     0       5.747  -3.877   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.748   1.513   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.748   6.133   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.415  -0.797   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -1.567   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415   0.743   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -3.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   1.513   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -5.417   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -3.107   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.748   3.053   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.082   3.823   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -6.187   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -3.877   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   3.823   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   5.363   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.459   3.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415   5.363   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.459   6.187   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.854   3.791   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.854   5.395   0.000  0.00  0.00           C+0
CONECT    1   22                                                            
CONECT    2    8   10   11                                                  
CONECT    3    7   12                                                       
CONECT    4   17   19                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    3    5    9                                                  
CONECT    8    2    6                                                       
CONECT    9    7                                                            
CONECT   10    2   14                                                       
CONECT   11    2   15                                                       
CONECT   12    3   13   16                                                  
CONECT   13   12   17   18                                                  
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   12   19                                                       
CONECT   17    4   13   20                                                  
CONECT   18   13   21                                                       
CONECT   19    4   16                                                       
CONECT   20   17   22                                                       
CONECT   21   18   22                                                       
CONECT   22    1   20   21                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0014746
HETATM    1  C1  UNL     1      -3.309  -1.571  -1.625  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.951  -0.095  -1.656  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.241   0.572  -0.447  1.00  0.00           N  
HETATM    4  C3  UNL     1      -4.615   0.736  -0.104  1.00  0.00           C  
HETATM    5  C4  UNL     1      -5.368  -0.501   0.247  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.529   1.753  -0.158  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.053   1.613   0.132  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.802   0.728   1.320  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.663   0.574   1.681  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.752  -0.312   2.860  1.00  0.00           C  
HETATM   11  N2  UNL     1       1.547   0.351   0.615  1.00  0.00           N  
HETATM   12  C10 UNL     1       2.611  -0.564   0.459  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.719  -1.774   1.075  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.778  -2.624   0.762  1.00  0.00           C  
HETATM   15  N3  UNL     1       4.712  -2.312  -0.127  1.00  0.00           N  
HETATM   16  C13 UNL     1       4.652  -1.133  -0.762  1.00  0.00           C  
HETATM   17  C14 UNL     1       5.661  -0.846  -1.679  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.585   0.369  -2.304  1.00  0.00           C  
HETATM   19 CL1  UNL     1       6.815   0.833  -3.483  1.00  0.00          CL  
HETATM   20  C16 UNL     1       4.585   1.273  -2.062  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.598   0.932  -1.132  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.622  -0.262  -0.482  1.00  0.00           C  
HETATM   23  H1  UNL     1      -2.873  -2.102  -0.764  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.375  -1.775  -1.816  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.778  -2.003  -2.528  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.858  -0.066  -1.839  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.507   0.330  -2.542  1.00  0.00           H  
HETATM   28  H6  UNL     1      -5.164   1.374  -0.857  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.626   1.388   0.822  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.758  -1.366   0.503  1.00  0.00           H  
HETATM   31  H9  UNL     1      -6.044  -0.331   1.142  1.00  0.00           H  
HETATM   32  H10 UNL     1      -6.113  -0.694  -0.579  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.980   2.199   0.777  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.684   2.534  -0.937  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.708   2.642   0.450  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.470   1.383  -0.765  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.245  -0.284   1.238  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.303   1.208   2.187  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.889   1.656   2.108  1.00  0.00           H  
HETATM   40  H18 UNL     1       1.761  -0.468   3.269  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.228   0.217   3.759  1.00  0.00           H  
HETATM   42  H20 UNL     1       0.198  -1.257   2.793  1.00  0.00           H  
HETATM   43  H21 UNL     1       1.372   0.970  -0.271  1.00  0.00           H  
HETATM   44  H22 UNL     1       1.980  -2.098   1.778  1.00  0.00           H  
HETATM   45  H23 UNL     1       3.803  -3.586   1.299  1.00  0.00           H  
HETATM   46  H24 UNL     1       6.469  -1.508  -1.911  1.00  0.00           H  
HETATM   47  H25 UNL     1       4.518   2.221  -2.544  1.00  0.00           H  
HETATM   48  H26 UNL     1       2.837   1.678  -0.953  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4    6
CONECT    4    5   28   29
CONECT    5   30   31   32
CONECT    6    7   33   34
CONECT    7    8   35   36
CONECT    8    9   37   38
CONECT    9   10   11   39
CONECT   10   40   41   42
CONECT   11   12   43
CONECT   12   13   13   22
CONECT   13   14   44
CONECT   14   15   15   45
CONECT   15   16
CONECT   16   17   17   22
CONECT   17   18   46
CONECT   18   19   20   20
CONECT   20   21   47
CONECT   21   22   22   48
END

HMDB0014746
     RDKit          3D
Chloroquine
 48 49  0  0  0  0  0  0  0  0999 V2000
   -3.3094   -1.5712   -1.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9510   -0.0947   -1.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    0.5721   -0.4469 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6155    0.7362   -0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3680   -0.5011    0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5285    1.7532   -0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    1.6135    0.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8018    0.7278    1.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6635    0.5735    1.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7518   -0.3123    2.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5469    0.3514    0.6154 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107   -0.5639    0.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7190   -1.7739    1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7777   -2.6241    0.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7118   -2.3123   -0.1270 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6521   -1.1333   -0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6607   -0.8463   -1.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5847    0.3687   -2.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8151    0.8325   -3.4834 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5849    1.2727   -2.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5980    0.9318   -1.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6215   -0.2620   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8730   -2.1017   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3747   -1.7747   -1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7783   -2.0031   -2.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8584   -0.0664   -1.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    0.3299   -2.5418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1639    1.3743   -0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6256    1.3883    0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7582   -1.3657    0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0439   -0.3314    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1127   -0.6941   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800    2.1989    0.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6842    2.5339   -0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7082    2.6418    0.4504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4697    1.3826   -0.7648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2452   -0.2838    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    1.2083    2.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8895    1.6559    2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -0.4682    3.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2277    0.2173    3.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1975   -1.2575    2.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3723    0.9700   -0.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9803   -2.0983    1.7779 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8034   -3.5863    1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4692   -1.5079   -1.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5177    2.2212   -2.5443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8367    1.6782   -0.9533 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
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 12  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 13 44  1  0
 14 45  1  0
 17 46  1  0
 20 47  1  0
 21 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Aralen	ChEBI
Artrichin	ChEBI
Bemaphate	ChEBI
Capquin	ChEBI
Chlorochin	ChEBI
Chloroquinum	ChEBI
Cloroquina	ChEBI
N(4)-(7-Chloro-4-quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine	ChEBI
Nivaquine b	ChEBI
Resoquine	ChEBI
Reumachlor	ChEBI
Sanoquin	ChEBI
Bemaphic acid	Generator
Chloraquine	HMDB
Chlorochine	HMDB
Chloroquina	HMDB
Chloroquinium	HMDB
Chlorquin	HMDB
Clorochina	HMDB
Chingamin	HMDB
Arechine	HMDB
Khingamin	HMDB
Sulphate, chloroquine	HMDB
Arequin	HMDB
Chloroquine sulfate	HMDB
Chloroquine sulphate	HMDB
Nivaquine	HMDB
Sulfate, chloroquine	HMDB

Chemical Formula

C₁₈H₂₆ClN₃

Average Molecular Weight

319.872

Monoisotopic Molecular Weight

319.181525554

IUPAC Name

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

Traditional Name

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

CAS Registry Number

54-05-7

SMILES

CCN(CC)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1

InChI Identifier

InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21)

InChI Key

WHTVZRBIWZFKQO-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
Tertiary aliphatic amine
Tertiary amine
Azacycle
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

tertiary amino compound (CHEBI:3638 )
organochlorine compound (CHEBI:3638 )
secondary amino compound (CHEBI:3638 )
aminoquinoline (CHEBI:3638 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014746)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	289 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.018 g/L	Not Available
LogP	4.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	176.8	30932474
[M+H]+	Not Available	175.554	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000968

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	5.28	ALOGPS
logP	3.93	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	10.32	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	28.16 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	96.42 m³·mol⁻¹	ChemAxon
Polarizability	37.29 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]+	180.484	30932474
DeepCCS	[M-H]-	178.126	30932474
DeepCCS	[M-2H]-	211.012	30932474
DeepCCS	[M+Na]+	186.577	30932474
AllCCS	[M+H]+	178.3	32859911
AllCCS	[M+H-H2O]+	175.3	32859911
AllCCS	[M+NH4]+	181.1	32859911
AllCCS	[M+Na]+	181.9	32859911
AllCCS	[M-H]-	181.0	32859911
AllCCS	[M+Na-2H]-	181.4	32859911
AllCCS	[M+HCOO]-	182.1	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.	5.96 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3537 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.42 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	175.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1227.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	185.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	138.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	154.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	343.0 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	321.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	354.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	696.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	70.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	647.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	450.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	445.2 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	31.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chloroquine	CCN(CC)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1	3479.3	Standard polar	33892256
Chloroquine	CCN(CC)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1	2630.9	Standard non polar	33892256
Chloroquine	CCN(CC)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1	2631.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chloroquine,1TMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2501.8	Semi standard non polar	33892256
Chloroquine,1TMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2556.7	Standard non polar	33892256
Chloroquine,1TMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	3066.3	Standard polar	33892256
Chloroquine,1TBDMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2690.1	Semi standard non polar	33892256
Chloroquine,1TBDMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2787.2	Standard non polar	33892256
Chloroquine,1TBDMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	3150.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Chloroquine CI-B (Non-derivatized)	splash10-00di-0009000000-d54119d64cfc341cee7d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Chloroquine CI-B (Non-derivatized)	splash10-00di-0009000000-d54119d64cfc341cee7d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chloroquine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pbi-9242000000-6cd79ce1c8a9ada4550d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chloroquine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-9320000000-2663c398ede2e502ca34	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloroquine 40V, Positive-QTOF	splash10-002p-8920000000-552012cb889bf65320d8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloroquine 20V, Positive-QTOF	splash10-0002-0391000000-7360fd3b6728bd6574b8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Chloroquine 10V, Positive-QTOF	splash10-00di-0029000000-3ea9f3105801d7abf080	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 10V, Positive-QTOF	splash10-00di-0119000000-8f9d4513bf5993f3c9c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 20V, Positive-QTOF	splash10-00dl-3957000000-e533e26da609c9329dae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 40V, Positive-QTOF	splash10-00bc-9530000000-646244109f4c47e0c2a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 10V, Negative-QTOF	splash10-014i-0009000000-d45e56a4f82a2d58657d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 20V, Negative-QTOF	splash10-014i-1229000000-09769326d92e55dd78aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 40V, Negative-QTOF	splash10-00fu-9630000000-f2986e805921cc8d3a37	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 10V, Positive-QTOF	splash10-00di-0049000000-7e55e664b21e89ddbe44	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 20V, Positive-QTOF	splash10-00dj-0198000000-64a0ed0e3e428bf65cbb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 40V, Positive-QTOF	splash10-004r-6950000000-75bff8c32e9dcca35dbf	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 10V, Negative-QTOF	splash10-014i-0009000000-b550e787bd639403cc76	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 20V, Negative-QTOF	splash10-014i-0109000000-3494d09f71ff43a3ce73	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chloroquine 40V, Negative-QTOF	splash10-004i-2910000000-efba909b8046e2bf2c67	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00608	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00608	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00608

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2618

KEGG Compound ID

C07625

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chloroquine

METLIN ID

Not Available

PubChem Compound

2719

PDB ID

Not Available

ChEBI ID

3638

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

Enzymes

Enzyme Details

1. Glutathione S-transferase A2

General function:: Involved in glutathione transferase activity
Specific function:: Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:: GSTA2
Uniprot ID:: P09210
Molecular weight:: 25663.675

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Tumor necrosis factor

General function:: Involved in tumor necrosis factor receptor binding
Specific function:: Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation
Gene Name:: TNF
Uniprot ID:: P01375
Molecular weight:: 25644.1

References

Jang CH, Choi JH, Byun MS, Jue DM: Chloroquine inhibits production of TNF-alpha, IL-1beta and IL-6 from lipopolysaccharide-stimulated human monocytes/macrophages by different modes. Rheumatology (Oxford). 2006 Jun;45(6):703-10. Epub 2006 Jan 17. [PubMed:16418198 ]
Rachmilewitz D, Karmeli F, Shteingart S, Lee J, Takabayashi K, Raz E: Immunostimulatory oligonucleotides inhibit colonic proinflammatory cytokine production in ulcerative colitis. Inflamm Bowel Dis. 2006 May;12(5):339-45. [PubMed:16670522 ]
Wozniacka A, Lesiak A, Narbutt J, McCauliffe DP, Sysa-Jedrzejowska A: Chloroquine treatment influences proinflammatory cytokine levels in systemic lupus erythematosus patients. Lupus. 2006;15(5):268-75. [PubMed:16761500 ]
Lim EJ, Lee SH, Lee JG, Chin BR, Bae YS, Kim JR, Lee CH, Baek SH: Activation of toll-like receptor-9 induces matrix metalloproteinase-9 expression through Akt and tumor necrosis factor-alpha signaling. FEBS Lett. 2006 Aug 7;580(18):4533-8. Epub 2006 Jul 17. [PubMed:16870179 ]
Dias-Melicio LA, Calvi SA, Bordon AP, Golim MA, Peracoli MT, Soares AM: Chloroquine is therapeutic in murine experimental model of paracoccidioidomycosis. FEMS Immunol Med Microbiol. 2007 Jun;50(1):133-43. Epub 2007 Apr 23. [PubMed:17456179 ]

Enzyme Details

8. Toll-like receptor 9

General function:: Involved in protein binding
Specific function:: Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific of microorganisms. TLR9 is a nucleotide-sensing TLR which is activated by unmethylated cytidine-phosphate-guanosine (CpG) dinucleotides. Acts via MYD88 and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the inflammatory response
Gene Name:: TLR9
Uniprot ID:: Q9NR96
Molecular weight:: 115858.7

References

Trevani AS, Chorny A, Salamone G, Vermeulen M, Gamberale R, Schettini J, Raiden S, Geffner J: Bacterial DNA activates human neutrophils by a CpG-independent pathway. Eur J Immunol. 2003 Nov;33(11):3164-74. [PubMed:14579285 ]
Rutz M, Metzger J, Gellert T, Luppa P, Lipford GB, Wagner H, Bauer S: Toll-like receptor 9 binds single-stranded CpG-DNA in a sequence- and pH-dependent manner. Eur J Immunol. 2004 Sep;34(9):2541-50. [PubMed:15307186 ]
Lenert P: Inhibitory oligodeoxynucleotides - therapeutic promise for systemic autoimmune diseases? Clin Exp Immunol. 2005 Apr;140(1):1-10. [PubMed:15762869 ]
Huang LY, Ishii KJ, Akira S, Aliberti J, Golding B: Th1-like cytokine induction by heat-killed Brucella abortus is dependent on triggering of TLR9. J Immunol. 2005 Sep 15;175(6):3964-70. [PubMed:16148144 ]
Merrell MA, Ilvesaro JM, Lehtonen N, Sorsa T, Gehrs B, Rosenthal E, Chen D, Shackley B, Harris KW, Selander KS: Toll-like receptor 9 agonists promote cellular invasion by increasing matrix metalloproteinase activity. Mol Cancer Res. 2006 Jul;4(7):437-47. [PubMed:16849519 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]

Showing metabocard for Chloroquine (HMDB0014746)

MOL for HMDB0014746 (Chloroquine)

3D MOL for HMDB0014746 (Chloroquine)

3D SDF for HMDB0014746 (Chloroquine)

3D-SDF for HMDB0014746 (Chloroquine)

PDB for HMDB0014746 (Chloroquine)

3D PDB for HMDB0014746 (Chloroquine)

SMILES for HMDB0014746 (Chloroquine)

INCHI for HMDB0014746 (Chloroquine)

Structure for HMDB0014746 (Chloroquine)

3D Structure for HMDB0014746 (Chloroquine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References

Transporters

References