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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:44 UTC

HMDB ID

HMDB0014751

Secondary Accession Numbers

HMDB14751

Metabolite Identification

Common Name

Amodiaquine

Description

Amodiaquine is only found in individuals that have used or taken this drug. It is a 4-aminoquinoquinoline compound with anti-inflammatory properties. [PubChem]The mechanism of plasmodicidal action of amodiaquine 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. The drug binds the free heme preventing the parasite from converting it to a form less toxic. This drug-heme complex is toxic and disrupts membrane function.

Structure

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

HMDB0014751
     RDKit          3D
Amodiaquine
 47 49  0  0  0  0  0  0  0  0999 V2000
   -4.1760    1.1772    1.8722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9325    0.9792    0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8062   -0.3277   -0.0734 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9678   -1.1815   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0010   -0.7702   -1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5826   -1.0179   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4522   -0.2657   -0.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434   -0.1799    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8994    0.3909   -0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0603    0.3953    0.3071 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457    0.0025   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5088   -0.5962   -1.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458   -1.0487   -1.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7783   -0.9164   -0.8741 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6936   -0.3502    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7826   -0.2452    1.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7090    0.3459    2.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1106    0.4223    3.4338 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4862    0.8235    2.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3906    0.7020    1.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4387    0.1218    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    0.8905   -1.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    0.8301   -2.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    0.2390   -1.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6862    0.2004   -2.7206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3652    0.9105    2.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464    0.7170    2.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401    2.2877    2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0431    1.6041    0.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8120    1.4623   -0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5871   -2.2032   -0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3890   -1.2501    1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9139   -1.3437   -2.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9639    0.2924   -1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0566   -0.9986   -0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135   -1.9487   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2845   -1.3925    0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2246   -0.5765    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9514    0.7024    1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599   -0.7112   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9267   -1.5319   -2.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7647   -0.6115    0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3765    1.3008    3.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250    1.1027    2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795    1.3711   -2.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    1.2357   -3.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080   -0.1946   -2.3414 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  7  1  0
 21 11  1  0
 21 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
 10 39  1  0
 12 40  1  0
 13 41  1  0
 16 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
M  END

613
  Mrv0541 02231214482D          

 25 27  0  0  0  0            999 V2000
    9.5637    2.3239    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.8210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.5835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6514   -0.1710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6514    2.3040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6514    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658    1.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3658    1.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    1.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1033    0.6254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1033    2.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369    1.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8509    1.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8509    1.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  1  0  0  0  0
  2 12  1  0  0  0  0
  3  6  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4 11  1  0  0  0  0
  4 16  1  0  0  0  0
  5 19  2  0  0  0  0
  5 23  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  2  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  2  0  0  0  0
 11 15  1  0  0  0  0
 12 17  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
 18 19  1  0  0  0  0
 18 21  1  0  0  0  0
 19 22  1  0  0  0  0
 20 23  2  0  0  0  0
 21 24  2  0  0  0  0
 22 25  2  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014751

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)

> <INCHI_KEY>
OVCDSSHSILBFBN-UHFFFAOYSA-N

> <FORMULA>
C20H22ClN3O

> <MOLECULAR_WEIGHT>
355.861

> <EXACT_MASS>
355.145140048

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.894067086153626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol

> <ALOGPS_LOGP>
4.83

> <JCHEM_LOGP>
3.7630057371844083

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.12454876031753

> <JCHEM_PKA_STRONGEST_BASIC>
10.227252328902408

> <JCHEM_POLAR_SURFACE_AREA>
48.39

> <JCHEM_REFRACTIVITY>
103.29110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amodiaquine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014751
     RDKit          3D
Amodiaquine
 47 49  0  0  0  0  0  0  0  0999 V2000
   -4.1760    1.1772    1.8722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9325    0.9792    0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8062   -0.3277   -0.0734 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9678   -1.1815   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0010   -0.7702   -1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5826   -1.0179   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4522   -0.2657   -0.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434   -0.1799    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8994    0.3909   -0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0603    0.3953    0.3071 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457    0.0025   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5088   -0.5962   -1.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458   -1.0487   -1.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7783   -0.9164   -0.8741 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6936   -0.3502    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7826   -0.2452    1.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7090    0.3459    2.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1106    0.4223    3.4338 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4862    0.8235    2.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3906    0.7020    1.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4387    0.1218    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    0.8905   -1.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    0.8301   -2.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    0.2390   -1.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6862    0.2004   -2.7206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3652    0.9105    2.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464    0.7170    2.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401    2.2877    2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0431    1.6041    0.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8120    1.4623   -0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5871   -2.2032   -0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3890   -1.2501    1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9139   -1.3437   -2.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9639    0.2924   -1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0566   -0.9986   -0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135   -1.9487   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2845   -1.3925    0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2246   -0.5765    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9514    0.7024    1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599   -0.7112   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9267   -1.5319   -2.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7647   -0.6115    0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3765    1.3008    3.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250    1.1027    2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795    1.3711   -2.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    1.2357   -3.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080   -0.1946   -2.3414 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  7  1  0
 21 11  1  0
 21 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
 10 39  1  0
 12 40  1  0
 13 41  1  0
 16 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 613                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      17.852   4.338   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0       7.081  -3.399   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.747  -1.089   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      12.416  -0.319   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      12.416   4.301   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.081  -0.319   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.415  -1.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.747  -2.629   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -0.319   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748  -0.319   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082  -1.089   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -2.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -3.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -1.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.082  -2.629   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.416   1.221   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748  -3.399   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.749   1.991   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.749   3.531   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.082   1.991   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.126   1.167   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.126   4.354   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.082   3.531   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.522   1.959   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.522   3.563   0.000  0.00  0.00           C+0
CONECT    1   25                                                            
CONECT    2   12                                                            
CONECT    3    6    8    9                                                  
CONECT    4   11   16                                                       
CONECT    5   19   23                                                       
CONECT    6    3    7                                                       
CONECT    7    6   10   12                                                  
CONECT    8    3   13                                                       
CONECT    9    3   14                                                       
CONECT   10    7   11                                                       
CONECT   11    4   10   15                                                  
CONECT   12    2    7   17                                                  
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15   11   17                                                       
CONECT   16    4   18   20                                                  
CONECT   17   12   15                                                       
CONECT   18   16   19   21                                                  
CONECT   19    5   18   22                                                  
CONECT   20   16   23                                                       
CONECT   21   18   24                                                       
CONECT   22   19   25                                                       
CONECT   23    5   20                                                       
CONECT   24   21   25                                                       
CONECT   25    1   22   24                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0014751
HETATM    1  C1  UNL     1      -4.176   1.177   1.872  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.933   0.979   0.403  1.00  0.00           C  
HETATM    3  N1  UNL     1      -3.806  -0.328  -0.073  1.00  0.00           N  
HETATM    4  C3  UNL     1      -4.968  -1.181  -0.031  1.00  0.00           C  
HETATM    5  C4  UNL     1      -6.001  -0.770  -1.023  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.583  -1.018  -0.092  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.452  -0.266  -0.698  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.243  -0.180   0.003  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.899   0.391  -0.517  1.00  0.00           C  
HETATM   10  N2  UNL     1       2.060   0.395   0.307  1.00  0.00           N  
HETATM   11  C9  UNL     1       3.346   0.003  -0.110  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.509  -0.596  -1.352  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.746  -1.049  -1.712  1.00  0.00           C  
HETATM   14  N3  UNL     1       5.778  -0.916  -0.874  1.00  0.00           N  
HETATM   15  C12 UNL     1       5.694  -0.350   0.331  1.00  0.00           C  
HETATM   16  C13 UNL     1       6.783  -0.245   1.138  1.00  0.00           C  
HETATM   17  C14 UNL     1       6.709   0.346   2.407  1.00  0.00           C  
HETATM   18 CL1  UNL     1       8.111   0.422   3.434  1.00  0.00          CL  
HETATM   19  C15 UNL     1       5.486   0.823   2.807  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.391   0.702   1.962  1.00  0.00           C  
HETATM   21  C17 UNL     1       4.439   0.122   0.718  1.00  0.00           C  
HETATM   22  C18 UNL     1       0.799   0.891  -1.785  1.00  0.00           C  
HETATM   23  C19 UNL     1      -0.364   0.830  -2.504  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.513   0.239  -1.955  1.00  0.00           C  
HETATM   25  O1  UNL     1      -2.686   0.200  -2.721  1.00  0.00           O  
HETATM   26  H1  UNL     1      -3.365   0.910   2.537  1.00  0.00           H  
HETATM   27  H2  UNL     1      -5.146   0.717   2.205  1.00  0.00           H  
HETATM   28  H3  UNL     1      -4.340   2.288   2.007  1.00  0.00           H  
HETATM   29  H4  UNL     1      -3.043   1.604   0.121  1.00  0.00           H  
HETATM   30  H5  UNL     1      -4.812   1.462  -0.126  1.00  0.00           H  
HETATM   31  H6  UNL     1      -4.587  -2.203  -0.323  1.00  0.00           H  
HETATM   32  H7  UNL     1      -5.389  -1.250   1.001  1.00  0.00           H  
HETATM   33  H8  UNL     1      -5.914  -1.344  -2.003  1.00  0.00           H  
HETATM   34  H9  UNL     1      -5.964   0.292  -1.329  1.00  0.00           H  
HETATM   35  H10 UNL     1      -7.057  -0.999  -0.697  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.714  -1.949  -0.734  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.285  -1.393   0.930  1.00  0.00           H  
HETATM   38  H13 UNL     1      -0.225  -0.577   0.988  1.00  0.00           H  
HETATM   39  H14 UNL     1       1.951   0.702   1.331  1.00  0.00           H  
HETATM   40  H15 UNL     1       2.660  -0.711  -2.026  1.00  0.00           H  
HETATM   41  H16 UNL     1       4.927  -1.532  -2.662  1.00  0.00           H  
HETATM   42  H17 UNL     1       7.765  -0.611   0.839  1.00  0.00           H  
HETATM   43  H18 UNL     1       5.377   1.301   3.761  1.00  0.00           H  
HETATM   44  H19 UNL     1       3.425   1.103   2.303  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.680   1.371  -2.197  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.460   1.236  -3.519  1.00  0.00           H  
HETATM   47  H22 UNL     1      -3.508  -0.195  -2.341  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    6
CONECT    4    5   31   32
CONECT    5   33   34   35
CONECT    6    7   36   37
CONECT    7    8    8   24
CONECT    8    9   38
CONECT    9   10   22   22
CONECT   10   11   39
CONECT   11   12   12   21
CONECT   12   13   40
CONECT   13   14   14   41
CONECT   14   15
CONECT   15   16   16   21
CONECT   16   17   42
CONECT   17   18   19   19
CONECT   19   20   43
CONECT   20   21   21   44
CONECT   22   23   45
CONECT   23   24   24   46
CONECT   24   25
CONECT   25   47
END

HMDB0014751
     RDKit          3D
Amodiaquine
 47 49  0  0  0  0  0  0  0  0999 V2000
   -4.1760    1.1772    1.8722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9325    0.9792    0.4026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8062   -0.3277   -0.0734 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9678   -1.1815   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0010   -0.7702   -1.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5826   -1.0179   -0.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4522   -0.2657   -0.6981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434   -0.1799    0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8994    0.3909   -0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0603    0.3953    0.3071 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457    0.0025   -0.1096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5088   -0.5962   -1.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458   -1.0487   -1.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7783   -0.9164   -0.8741 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6936   -0.3502    0.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7826   -0.2452    1.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7090    0.3459    2.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1106    0.4223    3.4338 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.4862    0.8235    2.8068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3906    0.7020    1.9618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4387    0.1218    0.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    0.8905   -1.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3642    0.8301   -2.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    0.2390   -1.9552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6862    0.2004   -2.7206 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3652    0.9105    2.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1464    0.7170    2.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3401    2.2877    2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0431    1.6041    0.1207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8120    1.4623   -0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5871   -2.2032   -0.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3890   -1.2501    1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9139   -1.3437   -2.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9639    0.2924   -1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0566   -0.9986   -0.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7135   -1.9487   -0.7343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2845   -1.3925    0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2246   -0.5765    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9514    0.7024    1.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6599   -0.7112   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9267   -1.5319   -2.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7647   -0.6115    0.8386 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3765    1.3008    3.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250    1.1027    2.3029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6795    1.3711   -2.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4597    1.2357   -3.5188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080   -0.1946   -2.3414 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24  7  1  0
 21 11  1  0
 21 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  5 35  1  0
  6 36  1  0
  6 37  1  0
  8 38  1  0
 10 39  1  0
 12 40  1  0
 13 41  1  0
 16 42  1  0
 19 43  1  0
 20 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Amodiaquina	ChEBI
Amodiaquinum	ChEBI
Amodiaquin	HMDB
Amodiaquine usp24	HMDB
Amodiaquine, ring-closed	HMDB
Camoquin	HMDB
Flavoquine	HMDB
Hydrochloride, amodiaquine	HMDB
Roussel brand OF amodiaquine hydrochloride	HMDB
Amodiachin	HMDB
Amodiaquine hydrochloride	HMDB
Camoquine	HMDB

Chemical Formula

C₂₀H₂₂ClN₃O

Average Molecular Weight

355.861

Monoisotopic Molecular Weight

355.145140048

IUPAC Name

4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol

Traditional Name

amodiaquine

CAS Registry Number

86-42-0

SMILES

CCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1

InChI Identifier

InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)

InChI Key

OVCDSSHSILBFBN-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
Haloquinoline
4-aminoquinoline
Aminophenol
P-aminophenol
Phenylmethylamine
Benzylamine
Aniline or substituted anilines
Aminopyridine
Phenol
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Aryl chloride
Monocyclic benzene moiety
Aryl halide
Pyridine
Benzenoid
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Secondary amine
Azacycle
Amine
Organochloride
Organohalogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

quinolines (CHEBI:2674 )
phenols (CHEBI:2674 )
a small molecule (CPD-10889 )

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

Cytoplasm (HMDB: HMDB0014751)
Membrane (HMDB: HMDB0014751)

Source

Exogenous

Exogenous (HMDB: HMDB0014751)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	208 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0088 g/L	Not Available
LogP	3.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	191.937	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000940

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0088 g/L	ALOGPS
logP	4.83	ALOGPS
logP	3.76	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.12	ChemAxon
pKa (Strongest Basic)	10.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	48.39 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.29 m³·mol⁻¹	ChemAxon
Polarizability	38.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	191.545	30932474
DeepCCS	[M-H]-	189.115	30932474
DeepCCS	[M-2H]-	223.619	30932474
DeepCCS	[M+Na]+	199.909	30932474
AllCCS	[M+H]+	184.2	32859911
AllCCS	[M+H-H2O]+	181.2	32859911
AllCCS	[M+NH4]+	187.0	32859911
AllCCS	[M+Na]+	187.8	32859911
AllCCS	[M-H]-	186.2	32859911
AllCCS	[M+Na-2H]-	185.7	32859911
AllCCS	[M+HCOO]-	185.4	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.	5.33 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6704 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.99 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	66.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1188.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	196.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	110.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	148.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	57.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	348.5 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	355.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	206.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	668.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	49.5 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	709.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	169.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	245.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	425.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	405.0 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	51.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Amodiaquine	CCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1	4392.0	Standard polar	33892256
Amodiaquine	CCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1	3077.9	Standard non polar	33892256
Amodiaquine	CCN(CC)CC1=C(O)C=CC(NC2=C3C=CC(Cl)=CC3=NC=C2)=C1	3384.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Amodiaquine,1TMS,isomer #1	CCN(CC)CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C	3190.0	Semi standard non polar	33892256
Amodiaquine,1TMS,isomer #2	CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O	3023.9	Semi standard non polar	33892256
Amodiaquine,2TMS,isomer #1	CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3024.2	Semi standard non polar	33892256
Amodiaquine,2TMS,isomer #1	CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	2938.5	Standard non polar	33892256
Amodiaquine,2TMS,isomer #1	CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3483.6	Standard polar	33892256
Amodiaquine,1TBDMS,isomer #1	CCN(CC)CC1=CC(NC2=CC=NC3=CC(Cl)=CC=C23)=CC=C1O[Si](C)(C)C(C)(C)C	3389.3	Semi standard non polar	33892256
Amodiaquine,1TBDMS,isomer #2	CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O	3230.9	Semi standard non polar	33892256
Amodiaquine,2TBDMS,isomer #1	CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3397.2	Semi standard non polar	33892256
Amodiaquine,2TBDMS,isomer #1	CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3353.8	Standard non polar	33892256
Amodiaquine,2TBDMS,isomer #1	CCN(CC)CC1=CC(N(C2=CC=NC3=CC(Cl)=CC=C23)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3619.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Amodiaquine GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-5039000000-deb48fd096e8eab87805	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amodiaquine GC-MS (1 TMS) - 70eV, Positive	splash10-03di-7009800000-7089f4eec8e0b64bba2c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Amodiaquine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amodiaquine LC-ESI-qTof , Positive-QTOF	splash10-0570-3940000000-2d4500c74767ebc68cf0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amodiaquine LC-ESI-qTof , Positive-QTOF	splash10-001i-1390000000-e476bc93f0f2236bccdc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amodiaquine , positive-QTOF	splash10-0570-3940000000-2d4500c74767ebc68cf0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Amodiaquine , positive-QTOF	splash10-001i-1390000000-e476bc93f0f2236bccdc	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 10V, Positive-QTOF	splash10-0a4i-0039000000-62adbcf1b80da6582ca1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 20V, Positive-QTOF	splash10-001i-1393000000-c73e48e7cfd7d390ddfa	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 40V, Positive-QTOF	splash10-0kcs-2190000000-8de404d259f2e431ba08	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 10V, Negative-QTOF	splash10-0udi-1009000000-c665029b31d3d0ae731b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 20V, Negative-QTOF	splash10-0udi-4119000000-d9ade9d08becc9d7fe95	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 40V, Negative-QTOF	splash10-00dl-9111000000-e7bdd6a9f825f1429a1e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 10V, Positive-QTOF	splash10-0a59-0089000000-228889052bdf8049fae3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 20V, Positive-QTOF	splash10-001i-0090000000-d45ee7ba1c5cd27865fa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 40V, Positive-QTOF	splash10-053r-0290000000-333fe4ea622efd6132be	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 10V, Negative-QTOF	splash10-0udi-0019000000-398809cbbc619aca8878	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 20V, Negative-QTOF	splash10-0f89-1089000000-3e1ecc2c9b62f8073845	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Amodiaquine 40V, Negative-QTOF	splash10-00lr-2290000000-6c33a84366a5268dd9dd	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 DB00613	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00613	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00613

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2080

KEGG Compound ID

C07626

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Amodiaquine

METLIN ID

Not Available

PubChem Compound

2165

PDB ID

CQA

ChEBI ID

2674

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

Harrison AC, Kitteringham NR, Clarke JB, Park BK: The mechanism of bioactivation and antigen formation of amodiaquine in the rat. Biochem Pharmacol. 1992 Apr 1;43(7):1421-30. [PubMed:1567466 ]
Jewell H, Maggs JL, Harrison AC, O'Neill PM, Ruscoe JE, Park BK: Role of hepatic metabolism in the bioactivation and detoxication of amodiaquine. Xenobiotica. 1995 Feb;25(2):199-217. [PubMed:7618347 ]

Enzymes

Enzyme Details

1. Histamine N-methyltransferase

General function:: Involved in histamine N-methyltransferase activity
Specific function:: Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name:: HNMT
Uniprot ID:: P50135
Molecular weight:: 6045.9

References

Yokoyama A, Mori S, Takahashi HK, Kanke T, Wake H, Nishibori M: Effect of amodiaquine, a histamine N-methyltransferase inhibitor, on, Propionibacterium acnes and lipopolysaccharide-induced hepatitis in mice. Eur J Pharmacol. 2007 Mar 8;558(1-3):179-84. Epub 2006 Nov 22. [PubMed:17222819 ]
Nowak JZ, Zandarowska E: Effect of amodiaquine on histamine level and histamine-methyltransferase activity in the rat brain. Arch Immunol Ther Exp (Warsz). 1980;28(6):927-30. [PubMed:6789797 ]
Barth H, Lorenz W, Troidl H: Effect of amodiaquine on gastric histamine methyltransferase and on histamine-stimulated gastric secretion. Br J Pharmacol. 1975 Nov;55(3):321-7. [PubMed:1203620 ]
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 2C9

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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

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 1B1

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. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

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 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

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 ]
Li XQ, Bjorkman A, Andersson TB, Ridderstrom M, Masimirembwa CM: Amodiaquine clearance and its metabolism to N-desethylamodiaquine is mediated by CYP2C8: a new high affinity and turnover enzyme-specific probe substrate. J Pharmacol Exp Ther. 2002 Feb;300(2):399-407. [PubMed:11805197 ]
Walsky RL, Obach RS: Validated assays for human cytochrome P450 activities. Drug Metab Dispos. 2004 Jun;32(6):647-60. [PubMed:15155557 ]

Showing metabocard for Amodiaquine (HMDB0014751)

MOL for HMDB0014751 (Amodiaquine)

3D MOL for HMDB0014751 (Amodiaquine)

3D SDF for HMDB0014751 (Amodiaquine)

3D-SDF for HMDB0014751 (Amodiaquine)

PDB for HMDB0014751 (Amodiaquine)

3D PDB for HMDB0014751 (Amodiaquine)

SMILES for HMDB0014751 (Amodiaquine)

INCHI for HMDB0014751 (Amodiaquine)

Structure for HMDB0014751 (Amodiaquine)

3D Structure for HMDB0014751 (Amodiaquine)

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