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enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:01 UTC

HMDB ID

HMDB0015549

Secondary Accession Numbers

HMDB15549

Metabolite Identification

Common Name

Hydroxychloroquine

Description

Hydroxychloroquine is only found in individuals that have used or taken this drug. It is a chemotherapeutic agent that acts against erythrocytic forms of malarial parasites.Although the exact mechanism of action is unknown, it may be based on ability of hydroxychloroquine to bind to and alter DNA. Hydroxychloroquine has also has been found to be taken up into the acidic food vacuoles of the parasite in the erythrocyte. This increases the pH of the acid vesicles, interfering with vesicle functions and possibly inhibiting phospholipid metabolism. In suppressive treatment, hydroxychloroquine inhibits the erythrocytic stage of development of plasmodia. In acute attacks of malaria, it interrupts erythrocytic schizogony of the parasite. Its ability to concentrate in parasitized erythrocytes may account for their selective toxicity against the erythrocytic stages of plasmodial infection. As an antirheumatic, hydroxychloroquine is thought to act as a mild immunosuppressant, inhibiting the production of rheumatoid factor and acute phase reactants. It also accumulates in white blood cells, stabilizing lysosomal membranes and inhibiting the activity of many enzymes, including collagenase and the proteases that cause cartilage breakdown.

Structure

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

HMDB0015549
     RDKit          3D
Hydroxychloroquine
 49 50  0  0  0  0  0  0  0  0999 V2000
   -3.5953   -2.5737   -0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5228   -1.1287   -1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9653   -0.2651   -0.1796 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9048   -0.2096    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895    0.6815    2.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197    1.9966    1.6930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849   -0.7977    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7201   -0.6725   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    0.7715   -1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305    1.5583   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539    3.0139   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    0.8812    0.3669 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3857    0.7245   -0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833    1.4020   -1.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9191    1.2777   -1.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8428    0.4915   -1.4417 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5662   -0.1867   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5248   -1.0113    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3116   -1.7290    1.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6172   -2.7426    2.0480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0913   -1.6362    2.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1126   -0.8184    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382   -0.0946    0.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -3.1116   -0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1865   -2.7970    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1798   -3.0609   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0377   -0.9870   -2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6021   -0.8044   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8425    0.2442    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2098   -1.2045    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3026    0.6520    2.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771    0.3407    2.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569    2.1459    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8154   -1.8894    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523   -0.3432    1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970   -1.2617   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2760   -1.1179   -0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713    1.2056   -1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0547    0.8715   -2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412    1.5286    0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313    3.3028   -1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260    3.5893    0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    3.4134   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9901    0.4602    1.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9505    2.0793   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244    1.8427   -2.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716   -1.0586   -0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9116   -2.2026    2.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1833   -0.7699    1.9911 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
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 13  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 14 45  1  0
 15 46  1  0
 18 47  1  0
 21 48  1  0
 22 49  1  0
M  END

1611
  Mrv0541 02231215352D          

 23 24  0  0  1  0            999 V2000
    8.1347    3.8460    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.5989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.5364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    1.3511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    3.8261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -1.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223    2.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.7739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    2.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    2.5886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    3.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    2.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    3.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6743    3.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    2.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4219    3.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 14  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  0  0  0  0
  3 12  1  0  0  0  0
  4  8  1  0  0  0  0
  4 13  1  0  0  0  0
  5 18  2  0  0  0  0
  5 20  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
 10 14  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 20  2  0  0  0  0
 18 21  1  0  0  0  0
 19 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015549

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)

> <INCHI_KEY>
XXSMGPRMXLTPCZ-UHFFFAOYSA-N

> <FORMULA>
C18H26ClN3O

> <MOLECULAR_WEIGHT>
335.872

> <EXACT_MASS>
335.176440176

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.30186921343052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.87

> <JCHEM_LOGP>
2.8869711746666673

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.59329056231384

> <JCHEM_PKA_STRONGEST_BASIC>
9.757020259065293

> <JCHEM_POLAR_SURFACE_AREA>
48.39

> <JCHEM_REFRACTIVITY>
97.96670000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxychloroquine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015549
     RDKit          3D
Hydroxychloroquine
 49 50  0  0  0  0  0  0  0  0999 V2000
   -3.5953   -2.5737   -0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5228   -1.1287   -1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9653   -0.2651   -0.1796 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9048   -0.2096    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895    0.6815    2.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197    1.9966    1.6930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849   -0.7977    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7201   -0.6725   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    0.7715   -1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305    1.5583   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539    3.0139   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    0.8812    0.3669 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3857    0.7245   -0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833    1.4020   -1.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9191    1.2777   -1.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8428    0.4915   -1.4417 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5662   -0.1867   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5248   -1.0113    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3116   -1.7290    1.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6172   -2.7426    2.0480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0913   -1.6362    2.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1126   -0.8184    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382   -0.0946    0.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -3.1116   -0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1865   -2.7970    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1798   -3.0609   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0377   -0.9870   -2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6021   -0.8044   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8425    0.2442    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2098   -1.2045    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3026    0.6520    2.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771    0.3407    2.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569    2.1459    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8154   -1.8894    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523   -0.3432    1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970   -1.2617   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2760   -1.1179   -0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713    1.2056   -1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0547    0.8715   -2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412    1.5286    0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313    3.3028   -1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260    3.5893    0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    3.4134   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9901    0.4602    1.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9505    2.0793   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244    1.8427   -2.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716   -1.0586   -0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9116   -2.2026    2.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1833   -0.7699    1.9911 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
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 13  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 14 45  1  0
 15 46  1  0
 18 47  1  0
 21 48  1  0
 22 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1611                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      15.185   7.179   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       4.414  -6.718   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.747  -2.868   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       9.748   2.522   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       9.748   7.142   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       8.415   0.212   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081  -0.558   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   1.752   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -2.098   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -4.408   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   2.522   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -2.098   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748   4.062   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -5.178   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -2.868   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082   4.832   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   4.832   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.082   6.372   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.459   4.009   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   6.372   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.459   7.195   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.854   4.800   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.854   6.404   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   14                                                            
CONECT    3    9   10   12                                                  
CONECT    4    8   13                                                       
CONECT    5   18   20                                                       
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    4    6   11                                                  
CONECT    9    3    7                                                       
CONECT   10    3   14                                                       
CONECT   11    8                                                            
CONECT   12    3   15                                                       
CONECT   13    4   16   17                                                  
CONECT   14    2   10                                                       
CONECT   15   12                                                            
CONECT   16   13   18   19                                                  
CONECT   17   13   20                                                       
CONECT   18    5   16   21                                                  
CONECT   19   16   22                                                       
CONECT   20    5   17                                                       
CONECT   21   18   23                                                       
CONECT   22   19   23                                                       
CONECT   23    1   21   22                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0015549
HETATM    1  C1  UNL     1      -3.595  -2.574  -0.842  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.523  -1.129  -1.196  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.965  -0.265  -0.180  1.00  0.00           N  
HETATM    4  C3  UNL     1      -3.905  -0.210   0.928  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.489   0.681   2.048  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.320   1.997   1.693  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.685  -0.798   0.237  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.720  -0.673  -0.908  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.580   0.772  -1.306  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.030   1.558  -0.136  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.154   3.014  -0.440  1.00  0.00           C  
HETATM   12  N2  UNL     1       1.125   0.881   0.367  1.00  0.00           N  
HETATM   13  C10 UNL     1       2.386   0.724  -0.249  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.683   1.402  -1.399  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.919   1.278  -1.989  1.00  0.00           C  
HETATM   16  N3  UNL     1       4.843   0.491  -1.442  1.00  0.00           N  
HETATM   17  C13 UNL     1       4.566  -0.187  -0.303  1.00  0.00           C  
HETATM   18  C14 UNL     1       5.525  -1.011   0.272  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.312  -1.729   1.420  1.00  0.00           C  
HETATM   20 CL1  UNL     1       6.617  -2.743   2.048  1.00  0.00          CL  
HETATM   21  C16 UNL     1       4.091  -1.636   2.044  1.00  0.00           C  
HETATM   22  C17 UNL     1       3.113  -0.818   1.492  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.338  -0.095   0.327  1.00  0.00           C  
HETATM   24  H1  UNL     1      -2.617  -3.112  -0.881  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.186  -2.797   0.053  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.180  -3.061  -1.684  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.038  -0.987  -2.158  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.602  -0.804  -1.327  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.842   0.244   0.488  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.210  -1.204   1.282  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.303   0.652   2.814  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.577   0.341   2.577  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.157   2.146   0.738  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.815  -1.889   0.517  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.252  -0.343   1.124  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.097  -1.262  -1.795  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.276  -1.118  -0.657  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.571   1.206  -1.606  1.00  0.00           H  
HETATM   39  H16 UNL     1       0.055   0.872  -2.200  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.841   1.529   0.662  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.031   3.303  -1.488  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.626   3.589   0.142  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.125   3.413  -0.115  1.00  0.00           H  
HETATM   44  H21 UNL     1       0.990   0.460   1.335  1.00  0.00           H  
HETATM   45  H22 UNL     1       1.950   2.079  -1.884  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.124   1.843  -2.922  1.00  0.00           H  
HETATM   47  H24 UNL     1       6.472  -1.059  -0.249  1.00  0.00           H  
HETATM   48  H25 UNL     1       3.912  -2.203   2.959  1.00  0.00           H  
HETATM   49  H26 UNL     1       2.183  -0.770   1.991  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    7
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6   33
CONECT    7    8   34   35
CONECT    8    9   36   37
CONECT    9   10   38   39
CONECT   10   11   12   40
CONECT   11   41   42   43
CONECT   12   13   44
CONECT   13   14   14   23
CONECT   14   15   45
CONECT   15   16   16   46
CONECT   16   17
CONECT   17   18   18   23
CONECT   18   19   47
CONECT   19   20   21   21
CONECT   21   22   48
CONECT   22   23   23   49
END

HMDB0015549
     RDKit          3D
Hydroxychloroquine
 49 50  0  0  0  0  0  0  0  0999 V2000
   -3.5953   -2.5737   -0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5228   -1.1287   -1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9653   -0.2651   -0.1796 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9048   -0.2096    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4895    0.6815    2.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197    1.9966    1.6930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6849   -0.7977    0.2367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7201   -0.6725   -0.9078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    0.7715   -1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0305    1.5583   -0.1364 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539    3.0139   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    0.8812    0.3669 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3857    0.7245   -0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833    1.4020   -1.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9191    1.2777   -1.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8428    0.4915   -1.4417 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5662   -0.1867   -0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5248   -1.0113    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3116   -1.7290    1.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6172   -2.7426    2.0480 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0913   -1.6362    2.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1126   -0.8184    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3382   -0.0946    0.3272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6169   -3.1116   -0.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1865   -2.7970    0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1798   -3.0609   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0377   -0.9870   -2.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6021   -0.8044   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8425    0.2442    0.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2098   -1.2045    1.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3026    0.6520    2.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5771    0.3407    2.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1569    2.1459    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8154   -1.8894    0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523   -0.3432    1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0970   -1.2617   -1.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2760   -1.1179   -0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5713    1.2056   -1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0547    0.8715   -2.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8412    1.5286    0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313    3.3028   -1.4877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6260    3.5893    0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1253    3.4134   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9901    0.4602    1.3350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9505    2.0793   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244    1.8427   -2.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716   -1.0586   -0.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9116   -2.2026    2.9591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1833   -0.7699    1.9911 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
  3  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 13  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 14 45  1  0
 15 46  1  0
 18 47  1  0
 21 48  1  0
 22 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Hydroxychloroquine	ChEBI
2-((4-((7-Chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol	ChEBI
2-(N-(4-(7-Chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol	ChEBI
7-Chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline	ChEBI
7-Chloro-4-(4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino)quinoline	ChEBI
7-Chloro-4-[4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino]quinoline	ChEBI
7-Chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline	ChEBI
Hidroxicloroquina	ChEBI
Hydroxychloroquinum	ChEBI
NSC4375	ChEBI
Oxichlorochine	ChEBI
Oxichloroquine	ChEBI
Polirreumin	ChEBI
7-Chloro-4-(4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino)quinoline	Generator
7-Chloro-4-(4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino)quinoline	Generator
7-Chloro-4-[4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino]quinoline	Generator
7-Chloro-4-[4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino]quinoline	Generator
HCQ	HMDB
Oxychlorochin	HMDB
Hydroxychloroquine sulfate (1:1) salt	HMDB
Oxychloroquine	HMDB
Hydroxychlorochin	HMDB
Hydroxychloroquine sulfate	HMDB
Plaquenil	HMDB

Chemical Formula

C₁₈H₂₆ClN₃O

Average Molecular Weight

335.872

Monoisotopic Molecular Weight

335.176440176

IUPAC Name

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

Traditional Name

hydroxychloroquine

CAS Registry Number

118-42-3

SMILES

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

InChI Identifier

InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)

InChI Key

XXSMGPRMXLTPCZ-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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:5801 )
organochlorine compound (CHEBI:5801 )
secondary amino compound (CHEBI:5801 )
primary alcohol (CHEBI:5801 )
aminoquinoline (CHEBI:5801 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015549)
Membrane (HMDB: HMDB0015549)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

antirheumatic drug (HMDB: HMDB0015549)
dermatologic drug (HMDB: HMDB0015549)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antimalarial (HMDB: HMDB0015549)

Biological role

antimalarial (HMDB: HMDB0015549)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	90 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.026 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	180.2	30932474
[M+H]+	Not Available	178.427	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000934

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.026 g/L	ALOGPS
logP	3.87	ALOGPS
logP	2.89	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.59	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.39 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	97.97 m³·mol⁻¹	ChemAxon
Polarizability	38.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	180.45	30932474
DeepCCS	[M-H]-	178.092	30932474
DeepCCS	[M-2H]-	210.977	30932474
DeepCCS	[M+Na]+	186.547	30932474
AllCCS	[M+H]+	181.0	32859911
AllCCS	[M+H-H2O]+	178.2	32859911
AllCCS	[M+NH4]+	183.6	32859911
AllCCS	[M+Na]+	184.4	32859911
AllCCS	[M-H]-	182.1	32859911
AllCCS	[M+Na-2H]-	182.7	32859911
AllCCS	[M+HCOO]-	183.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxychloroquine	CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1	3812.3	Standard polar	33892256
Hydroxychloroquine	CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1	2862.3	Standard non polar	33892256
Hydroxychloroquine	CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1	2896.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxychloroquine,1TMS,isomer #1	CCN(CCCC(C)NC1=CC=NC2=CC(Cl)=CC=C12)CCO[Si](C)(C)C	2784.9	Semi standard non polar	33892256
Hydroxychloroquine,1TMS,isomer #2	CCN(CCO)CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C	2703.6	Semi standard non polar	33892256
Hydroxychloroquine,2TMS,isomer #1	CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C)CCO[Si](C)(C)C	2715.5	Semi standard non polar	33892256
Hydroxychloroquine,2TMS,isomer #1	CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C)CCO[Si](C)(C)C	2740.5	Standard non polar	33892256
Hydroxychloroquine,2TMS,isomer #1	CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C)CCO[Si](C)(C)C	3242.2	Standard polar	33892256
Hydroxychloroquine,1TBDMS,isomer #1	CCN(CCCC(C)NC1=CC=NC2=CC(Cl)=CC=C12)CCO[Si](C)(C)C(C)(C)C	3010.8	Semi standard non polar	33892256
Hydroxychloroquine,1TBDMS,isomer #2	CCN(CCO)CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C	2946.8	Semi standard non polar	33892256
Hydroxychloroquine,2TBDMS,isomer #1	CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C	3130.1	Semi standard non polar	33892256
Hydroxychloroquine,2TBDMS,isomer #1	CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C	3120.3	Standard non polar	33892256
Hydroxychloroquine,2TBDMS,isomer #1	CCN(CCCC(C)N(C1=CC=NC2=CC(Cl)=CC=C12)[Si](C)(C)C(C)(C)C)CCO[Si](C)(C)C(C)(C)C	3379.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxychloroquine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-9262000000-58dde1657b5d6098be9b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxychloroquine GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-9266000000-ea4f93631dd2ecfd327c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hydroxychloroquine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f6t-3972000000-7c193125680c0c9e276f	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 - Hydroxychloroquine 40V, Positive-QTOF	splash10-0002-0970000000-727b5fa0ccae5ed8e353	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxychloroquine 50V, Positive-QTOF	splash10-004l-0920000000-7ac7ca483022df09c0af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxychloroquine 10V, Positive-QTOF	splash10-000i-0009000000-4ef780743e3f6b698679	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxychloroquine 20V, Positive-QTOF	splash10-000j-0179000000-2cc295a00cfa8b906a76	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxychloroquine 40V, Positive-QTOF	splash10-0002-0970000000-7083c4ae0b9ffd9bdd65	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hydroxychloroquine 30V, Positive-QTOF	splash10-0002-0390000000-5a80b772bbcf76126d36	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 10V, Positive-QTOF	splash10-000i-0009000000-3ad87c8e6d06353b69a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 20V, Positive-QTOF	splash10-069a-3849000000-89ef84bf56d7c636c87a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 40V, Positive-QTOF	splash10-054n-9460000000-09312fdaefa09ffd4066	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 10V, Negative-QTOF	splash10-001i-0009000000-7d2e379f85931a4c8042	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 20V, Negative-QTOF	splash10-001i-1229000000-f952822a37d6efa233af	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 40V, Negative-QTOF	splash10-002f-9641000000-8b6d466c2c58b3345281	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 10V, Positive-QTOF	splash10-000i-0039000000-ef94af670ab631c9aa96	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 20V, Positive-QTOF	splash10-000b-0094000000-a09f3e2ffce0834eeb4d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 40V, Positive-QTOF	splash10-004i-6960000000-4349c6d77ff753227523	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 10V, Negative-QTOF	splash10-001i-0019000000-e3a3afc02d61a6461805	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 20V, Negative-QTOF	splash10-0fsl-0129000000-7fba6200eea5e933699f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxychloroquine 40V, Negative-QTOF	splash10-004i-1940000000-c48ff4523d2ef3631ba7	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB01611	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01611	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

DB01611

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3526

KEGG Compound ID

C07043

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hydroxychloroquine

METLIN ID

Not Available

PubChem Compound

3652

PDB ID

Not Available

ChEBI ID

5801

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. 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 ]
Somer M, Kallio J, Pesonen U, Pyykko K, Huupponen R, Scheinin M: Influence of hydroxychloroquine on the bioavailability of oral metoprolol. Br J Clin Pharmacol. 2000 Jun;49(6):549-54. [PubMed:10848718 ]

Enzyme Details

2. 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

Sun S, Rao NL, Venable J, Thurmond R, Karlsson L: TLR7/9 antagonists as therapeutics for immune-mediated inflammatory disorders. Inflamm Allergy Drug Targets. 2007 Dec;6(4):223-35. [PubMed:18220957 ]
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 ]

Showing metabocard for Hydroxychloroquine (HMDB0015549)

MOL for HMDB0015549 (Hydroxychloroquine)

3D MOL for HMDB0015549 (Hydroxychloroquine)

3D SDF for HMDB0015549 (Hydroxychloroquine)

3D-SDF for HMDB0015549 (Hydroxychloroquine)

PDB for HMDB0015549 (Hydroxychloroquine)

3D PDB for HMDB0015549 (Hydroxychloroquine)

SMILES for HMDB0015549 (Hydroxychloroquine)

INCHI for HMDB0015549 (Hydroxychloroquine)

Structure for HMDB0015549 (Hydroxychloroquine)

3D Structure for HMDB0015549 (Hydroxychloroquine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References