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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 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015219

Secondary Accession Numbers

HMDB15219

Metabolite Identification

Common Name

Primaquine

Description

An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404)

Structure

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

HMDB0015219
     RDKit          3D
Primaquine
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.0692    2.3923   -2.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609    1.6022   -1.7590 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6830    0.6384   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3621    0.3822   -0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0215   -0.5822    0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279   -0.8042    0.7308 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4316   -0.0881    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4675   -0.4173   -1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6821   -0.4289    0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9112    0.2418    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7659    1.7484    0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451    2.4035   -0.1260 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0158   -1.3156    0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608   -2.2855    1.9056 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344   -3.0046    2.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -2.8036    2.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3480   -1.8221    1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3279   -1.0784    0.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621   -0.1095   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5320    1.7265   -3.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5252    3.2263   -2.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3636    2.8479   -1.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167    0.9875   -0.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259   -1.5430    1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792    1.0040    0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -0.9873   -1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3163   -1.0862   -1.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719    0.4825   -2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8345   -1.5264    0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5385   -0.1136    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7750   -0.0157    0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1742   -0.0571   -0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7017    2.0058    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8575    2.1108   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6298    3.2647   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5319    1.7700   -0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132   -3.7899    3.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8706   -3.3817    2.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3795   -1.6377    1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139    0.0443   -0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  5 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  2  0
 19  3  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
M  END

1087
  Mrv0541 02231215142D          

 19 20  0  0  1  0            999 V2000
    2.8075    2.5246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.0495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930   -2.8381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885    0.8459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -2.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6885    2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4360    1.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    3.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 19  1  0  0  0  0
  2  5  1  0  0  0  0
  2  9  1  0  0  0  0
  3 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 18  2  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  7 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015219

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3

> <INCHI_KEY>
INDBQLZJXZLFIT-UHFFFAOYSA-N

> <FORMULA>
C15H21N3O

> <MOLECULAR_WEIGHT>
259.3467

> <EXACT_MASS>
259.168462309

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.92487918268025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
1.6429209590000005

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.109150282593124

> <JCHEM_PKA_STRONGEST_BASIC>
10.203764938153093

> <JCHEM_POLAR_SURFACE_AREA>
60.17

> <JCHEM_REFRACTIVITY>
78.51490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015219
     RDKit          3D
Primaquine
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.0692    2.3923   -2.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609    1.6022   -1.7590 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6830    0.6384   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3621    0.3822   -0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0215   -0.5822    0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279   -0.8042    0.7308 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4316   -0.0881    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4675   -0.4173   -1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6821   -0.4289    0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9112    0.2418    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7659    1.7484    0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451    2.4035   -0.1260 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0158   -1.3156    0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608   -2.2855    1.9056 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344   -3.0046    2.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -2.8036    2.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3480   -1.8221    1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3279   -1.0784    0.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621   -0.1095   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5320    1.7265   -3.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5252    3.2263   -2.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3636    2.8479   -1.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167    0.9875   -0.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259   -1.5430    1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792    1.0040    0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -0.9873   -1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3163   -1.0862   -1.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719    0.4825   -2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8345   -1.5264    0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5385   -0.1136    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7750   -0.0157    0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1742   -0.0571   -0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7017    2.0058    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8575    2.1108   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6298    3.2647   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5319    1.7700   -0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132   -3.7899    3.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8706   -3.3817    2.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3795   -1.6377    1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139    0.0443   -0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  5 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  2  0
 19  3  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1087                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.241   4.713   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       7.908   0.092   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       3.907  -5.298   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      10.619   1.579   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.574  -0.678   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574  -2.218   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.241  -2.988   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241   0.092   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908   1.632   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.241  -4.528   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.242   2.402   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574   2.402   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.242   3.942   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574   3.942   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.908   4.713   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.619   4.766   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.014   3.975   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.014   2.370   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.241   6.253   0.000  0.00  0.00           C+0
CONECT    1   14   19                                                       
CONECT    2    5    9                                                       
CONECT    3   10                                                            
CONECT    4   11   18                                                       
CONECT    5    2    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6   10                                                       
CONECT    8    5                                                            
CONECT    9    2   11   12                                                  
CONECT   10    3    7                                                       
CONECT   11    4    9   13                                                  
CONECT   12    9   14                                                       
CONECT   13   11   15   16                                                  
CONECT   14    1   12   15                                                  
CONECT   15   13   14                                                       
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18    4   17                                                       
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0015219
HETATM    1  C1  UNL     1       2.069   2.392  -2.401  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.061   1.602  -1.759  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.683   0.638  -0.846  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.362   0.382  -0.504  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.021  -0.582   0.407  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.328  -0.804   0.731  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.432  -0.088   0.108  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.467  -0.417  -1.339  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.682  -0.429   0.859  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.911   0.242   0.324  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.766   1.748   0.386  1.00  0.00           C  
HETATM   12  N2  UNL     1      -4.945   2.403  -0.126  1.00  0.00           N  
HETATM   13  C10 UNL     1       2.016  -1.316   0.997  1.00  0.00           C  
HETATM   14  N3  UNL     1       1.761  -2.286   1.906  1.00  0.00           N  
HETATM   15  C11 UNL     1       2.734  -3.005   2.484  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.066  -2.804   2.192  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.348  -1.822   1.270  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.328  -1.078   0.673  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.662  -0.109  -0.241  1.00  0.00           C  
HETATM   20  H1  UNL     1       1.532   1.727  -3.097  1.00  0.00           H  
HETATM   21  H2  UNL     1       2.525   3.226  -2.957  1.00  0.00           H  
HETATM   22  H3  UNL     1       1.364   2.848  -1.670  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.617   0.987  -0.990  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.526  -1.543   1.476  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.179   1.004   0.191  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.559  -0.987  -1.611  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.316  -1.086  -1.615  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.472   0.482  -2.020  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.834  -1.526   0.886  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.539  -0.114   1.913  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.775  -0.016   0.970  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.174  -0.057  -0.695  1.00  0.00           H  
HETATM   33  H14 UNL     1      -3.702   2.006   1.477  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.858   2.111  -0.140  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.630   3.265  -0.628  1.00  0.00           H  
HETATM   36  H17 UNL     1      -5.532   1.770  -0.684  1.00  0.00           H  
HETATM   37  H18 UNL     1       2.513  -3.790   3.221  1.00  0.00           H  
HETATM   38  H19 UNL     1       4.871  -3.382   2.655  1.00  0.00           H  
HETATM   39  H20 UNL     1       5.380  -1.638   1.017  1.00  0.00           H  
HETATM   40  H21 UNL     1       4.714   0.044  -0.468  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   23
CONECT    5    6   13   13
CONECT    6    7   24
CONECT    7    8    9   25
CONECT    8   26   27   28
CONECT    9   10   29   30
CONECT   10   11   31   32
CONECT   11   12   33   34
CONECT   12   35   36
CONECT   13   14   18
CONECT   14   15   15
CONECT   15   16   37
CONECT   16   17   17   38
CONECT   17   18   39
CONECT   18   19   19
CONECT   19   40
END

HMDB0015219
     RDKit          3D
Primaquine
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.0692    2.3923   -2.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0609    1.6022   -1.7590 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6830    0.6384   -0.8460 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3621    0.3822   -0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0215   -0.5822    0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279   -0.8042    0.7308 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4316   -0.0881    0.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4675   -0.4173   -1.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6821   -0.4289    0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9112    0.2418    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7659    1.7484    0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9451    2.4035   -0.1260 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0158   -1.3156    0.9969 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608   -2.2855    1.9056 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7344   -3.0046    2.4845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -2.8036    2.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3480   -1.8221    1.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3279   -1.0784    0.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621   -0.1095   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5320    1.7265   -3.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5252    3.2263   -2.9573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3636    2.8479   -1.6696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167    0.9875   -0.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259   -1.5430    1.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792    1.0040    0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586   -0.9873   -1.6107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3163   -1.0862   -1.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719    0.4825   -2.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8345   -1.5264    0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5385   -0.1136    1.9132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7750   -0.0157    0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1742   -0.0571   -0.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7017    2.0058    1.4774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8575    2.1108   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6298    3.2647   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5319    1.7700   -0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5132   -3.7899    3.2214 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8706   -3.3817    2.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3795   -1.6377    1.0175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139    0.0443   -0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  5 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  2  0
 19  3  1  0
 18 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 19 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Methoxy-8-(4-amino-1-methylbutylamino)quinoline	ChEBI
8-((4-Amino-1-methylbutyl)amino)-6-methoxyquinoline	ChEBI
8-(4-Amino-1-methylbutylamino)-6-methoxyquinoline	ChEBI
Neo-quipenyl	ChEBI
Primachin	ChEBI
Primachinum	ChEBI
Primaquin	ChEBI
Primaquina	ChEBI
Primaquinum	ChEBI
Kanaprim	Kegg
Diphosphate, primaquine	MeSH
Phosphate, primaquine	MeSH
Primacin	MeSH
Primaquine diphosphate	MeSH
Primaquine phosphate	MeSH
Boucher and muir brand OF primaquine phosphate	MeSH, HMDB

Chemical Formula

C₁₅H₂₁N₃O

Average Molecular Weight

259.3467

Monoisotopic Molecular Weight

259.168462309

IUPAC Name

N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine

Traditional Name

N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine

CAS Registry Number

90-34-6

SMILES

COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1

InChI Identifier

InChI=1S/C15H21N3O/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14/h4,6,8-11,18H,3,5,7,16H2,1-2H3

InChI Key

INDBQLZJXZLFIT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoquinolines and derivatives. These are organic compounds containing an amino group attached to a quinoline ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Aminoquinolines and derivatives

Direct Parent

Aminoquinolines and derivatives

Alternative Parents

Substituents

Aminoquinoline
Methoxyaniline
Anisole
Alkyl aryl ether
Secondary aliphatic/aromatic amine
Pyridine
Benzenoid
Heteroaromatic compound
Ether
Azacycle
Secondary amine
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:8405 )
N-substituted diamine (CHEBI:8405 )
aminoquinoline (CHEBI:8405 )

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: HMDB0015219)
Membrane (HMDB: HMDB0015219)

Source

Exogenous

Exogenous (HMDB: HMDB0015219)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.056 g/L	Not Available
LogP	2.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	161.335	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000982

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.056 g/L	ALOGPS
logP	2.76	ALOGPS
logP	1.64	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	17.11	ChemAxon
pKa (Strongest Basic)	10.2	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.17 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	78.51 m³·mol⁻¹	ChemAxon
Polarizability	29.92 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
DarkChem	[M+H]+	162.241	31661259
DarkChem	[M-H]-	163.825	31661259
DeepCCS	[M+H]+	164.758	30932474
DeepCCS	[M-H]-	162.4	30932474
DeepCCS	[M-2H]-	195.299	30932474
DeepCCS	[M+Na]+	170.851	30932474
AllCCS	[M+H]+	163.2	32859911
AllCCS	[M+H-H2O]+	159.6	32859911
AllCCS	[M+NH4]+	166.5	32859911
AllCCS	[M+Na]+	167.4	32859911
AllCCS	[M-H]-	166.2	32859911
AllCCS	[M+Na-2H]-	166.5	32859911
AllCCS	[M+HCOO]-	166.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.04 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0124 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.2 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	159.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Primaquine	COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1	3296.2	Standard polar	33892256
Primaquine	COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1	2331.7	Standard non polar	33892256
Primaquine	COC1=CC(NC(C)CCCN)=C2N=CC=CC2=C1	2442.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Primaquine,1TMS,isomer #1	COC1=CC(NC(C)CCCN[Si](C)(C)C)=C2N=CC=CC2=C1	2509.9	Semi standard non polar	33892256
Primaquine,1TMS,isomer #1	COC1=CC(NC(C)CCCN[Si](C)(C)C)=C2N=CC=CC2=C1	2438.6	Standard non polar	33892256
Primaquine,1TMS,isomer #1	COC1=CC(NC(C)CCCN[Si](C)(C)C)=C2N=CC=CC2=C1	3381.6	Standard polar	33892256
Primaquine,1TMS,isomer #2	COC1=CC(N(C(C)CCCN)[Si](C)(C)C)=C2N=CC=CC2=C1	2320.4	Semi standard non polar	33892256
Primaquine,1TMS,isomer #2	COC1=CC(N(C(C)CCCN)[Si](C)(C)C)=C2N=CC=CC2=C1	2448.8	Standard non polar	33892256
Primaquine,1TMS,isomer #2	COC1=CC(N(C(C)CCCN)[Si](C)(C)C)=C2N=CC=CC2=C1	3354.3	Standard polar	33892256
Primaquine,2TMS,isomer #1	COC1=CC(N(C(C)CCCN[Si](C)(C)C)[Si](C)(C)C)=C2N=CC=CC2=C1	2388.6	Semi standard non polar	33892256
Primaquine,2TMS,isomer #1	COC1=CC(N(C(C)CCCN[Si](C)(C)C)[Si](C)(C)C)=C2N=CC=CC2=C1	2569.5	Standard non polar	33892256
Primaquine,2TMS,isomer #1	COC1=CC(N(C(C)CCCN[Si](C)(C)C)[Si](C)(C)C)=C2N=CC=CC2=C1	2989.2	Standard polar	33892256
Primaquine,2TMS,isomer #2	COC1=CC(NC(C)CCCN([Si](C)(C)C)[Si](C)(C)C)=C2N=CC=CC2=C1	2614.2	Semi standard non polar	33892256
Primaquine,2TMS,isomer #2	COC1=CC(NC(C)CCCN([Si](C)(C)C)[Si](C)(C)C)=C2N=CC=CC2=C1	2617.8	Standard non polar	33892256
Primaquine,2TMS,isomer #2	COC1=CC(NC(C)CCCN([Si](C)(C)C)[Si](C)(C)C)=C2N=CC=CC2=C1	3267.2	Standard polar	33892256
Primaquine,3TMS,isomer #1	COC1=CC(N(C(C)CCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=C2N=CC=CC2=C1	2601.2	Semi standard non polar	33892256
Primaquine,3TMS,isomer #1	COC1=CC(N(C(C)CCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=C2N=CC=CC2=C1	2702.1	Standard non polar	33892256
Primaquine,3TMS,isomer #1	COC1=CC(N(C(C)CCCN([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C)=C2N=CC=CC2=C1	2925.7	Standard polar	33892256
Primaquine,1TBDMS,isomer #1	COC1=CC(NC(C)CCCN[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	2743.7	Semi standard non polar	33892256
Primaquine,1TBDMS,isomer #1	COC1=CC(NC(C)CCCN[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	2611.0	Standard non polar	33892256
Primaquine,1TBDMS,isomer #1	COC1=CC(NC(C)CCCN[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	3418.9	Standard polar	33892256
Primaquine,1TBDMS,isomer #2	COC1=CC(N(C(C)CCCN)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	2590.0	Semi standard non polar	33892256
Primaquine,1TBDMS,isomer #2	COC1=CC(N(C(C)CCCN)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	2662.3	Standard non polar	33892256
Primaquine,1TBDMS,isomer #2	COC1=CC(N(C(C)CCCN)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	3388.7	Standard polar	33892256
Primaquine,2TBDMS,isomer #1	COC1=CC(N(C(C)CCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	2851.1	Semi standard non polar	33892256
Primaquine,2TBDMS,isomer #1	COC1=CC(N(C(C)CCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	2940.3	Standard non polar	33892256
Primaquine,2TBDMS,isomer #1	COC1=CC(N(C(C)CCCN[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	3153.4	Standard polar	33892256
Primaquine,2TBDMS,isomer #2	COC1=CC(NC(C)CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	3054.0	Semi standard non polar	33892256
Primaquine,2TBDMS,isomer #2	COC1=CC(NC(C)CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	2954.1	Standard non polar	33892256
Primaquine,2TBDMS,isomer #2	COC1=CC(NC(C)CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	3345.3	Standard polar	33892256
Primaquine,3TBDMS,isomer #1	COC1=CC(N(C(C)CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	3270.1	Semi standard non polar	33892256
Primaquine,3TBDMS,isomer #1	COC1=CC(N(C(C)CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	3203.1	Standard non polar	33892256
Primaquine,3TBDMS,isomer #1	COC1=CC(N(C(C)CCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C2N=CC=CC2=C1	3163.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Primaquine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-7390000000-20feb8c491df9e9e6f0d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Primaquine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Primaquine 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 - Primaquine LC-ESI-qTof , Positive-QTOF	splash10-01r6-0970000000-a3b1021cda642a6141b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QFT , positive-QTOF	splash10-01p6-4290000000-d5f33ea098bbcd333ccf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QFT , positive-QTOF	splash10-000l-9360000000-9f32d7ddbda48f0e2dc5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QFT , positive-QTOF	splash10-002r-9530000000-5c70a8800c55df1915e7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QFT , positive-QTOF	splash10-002r-9810000000-89e3b0e2b3cb4d1e9293	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QFT , positive-QTOF	splash10-00n0-5900000000-cbe196964f610f8bf1ff	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QFT , positive-QTOF	splash10-00o9-3900000000-6209d7be74ea608e7fc2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QTOF , positive-QTOF	splash10-03di-0190000000-32ab0ba382901a73b1c0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QTOF , positive-QTOF	splash10-002f-1690000000-82416f4c3f338eece150	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QTOF , positive-QTOF	splash10-004i-0920000000-65f7b4135f0db6eee15e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QTOF , positive-QTOF	splash10-004i-0900000000-17b7474db1209213f689	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QTOF , positive-QTOF	splash10-001i-0900000000-b2c7e131a6a25d115853	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine , positive-QTOF	splash10-01r6-0970000000-a3b1021cda642a6141b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QFT , positive-QTOF	splash10-001i-2900000000-d3dfd1b72d458ffd07d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QFT , positive-QTOF	splash10-01p6-4290000000-314f515d08e6730a1df9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QFT , positive-QTOF	splash10-000l-9360000000-3933ab4d9c2c3918ecce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QFT , positive-QTOF	splash10-002r-9530000000-65625d68f98ae8f36ea0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine LC-ESI-QFT , positive-QTOF	splash10-002r-7910000000-6c3e274b81107c5e98eb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Primaquine 30V, Positive-QTOF	splash10-000l-9360000000-239fc11ba8db0d498ff2	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Primaquine 10V, Positive-QTOF	splash10-03dl-0090000000-045cb60c1f5b86235b8d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Primaquine 20V, Positive-QTOF	splash10-0296-4290000000-01a4b9c14070fa4302c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Primaquine 40V, Positive-QTOF	splash10-0006-9730000000-42103ce07831ca6222a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Primaquine 10V, Negative-QTOF	splash10-0a4i-0090000000-1af4abbe157a64d54565	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Primaquine 20V, Negative-QTOF	splash10-0a4i-1290000000-d23ff1647c1e20943a1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Primaquine 40V, Negative-QTOF	splash10-006x-2930000000-c2b4d4e6f2d8325f4a71	2016-08-03	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 DB01087	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01087	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01087

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4739

KEGG Compound ID

C07627

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Primaquine

METLIN ID

Not Available

PubChem Compound

4908

PDB ID

Not Available

ChEBI ID

8405

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

Mihaly GW, Ward SA, Edwards G, Nicholl DD, Orme ML, Breckenridge AM: Pharmacokinetics of primaquine in man. I. Studies of the absolute bioavailability and effects of dose size. Br J Clin Pharmacol. 1985 Jun;19(6):745-50. [PubMed:4027117 ]
Cohen RJ, Sachs JR, Wicker DJ, Conrad ME: Methemoglobinemia provoked by malarial chemoprophylaxis in Vietnam. N Engl J Med. 1968 Nov 21;279(21):1127-31. [PubMed:5686480 ]
Coleman MD, Coleman NA: Drug-induced methaemoglobinaemia. Treatment issues. Drug Saf. 1996 Jun;14(6):394-405. [PubMed:8828017 ]
ALVING AS, ARNOLD J, HOCKWALD RS, CLAYMAN CB, DERN RJ, BEUTLER E, FLANAGAN CL: Potentiation of the curative action of primaquine in vivax malaria by quinine and chloroquine. J Lab Clin Med. 1955 Aug;46(2):301-6. [PubMed:13242948 ]
Hill DR, Baird JK, Parise ME, Lewis LS, Ryan ET, Magill AJ: Primaquine: report from CDC expert meeting on malaria chemoprophylaxis I. Am J Trop Med Hyg. 2006 Sep;75(3):402-15. [PubMed:16968913 ]

Enzymes

Enzyme Details

1. Ribosyldihydronicotinamide dehydrogenase [quinone]

General function:: Involved in electron carrier activity
Specific function:: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:: NQO2
Uniprot ID:: P16083
Molecular weight:: 25918.4

References

Graves PR, Kwiek JJ, Fadden P, Ray R, Hardeman K, Coley AM, Foley M, Haystead TA: Discovery of novel targets of quinoline drugs in the human purine binding proteome. Mol Pharmacol. 2002 Dec;62(6):1364-72. [PubMed:12435804 ]

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 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 1A2

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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

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 ]

Showing metabocard for Primaquine (HMDB0015219)

MOL for HMDB0015219 (Primaquine)

3D MOL for HMDB0015219 (Primaquine)

3D SDF for HMDB0015219 (Primaquine)

3D-SDF for HMDB0015219 (Primaquine)

PDB for HMDB0015219 (Primaquine)

3D PDB for HMDB0015219 (Primaquine)

SMILES for HMDB0015219 (Primaquine)

INCHI for HMDB0015219 (Primaquine)

Structure for HMDB0015219 (Primaquine)

3D Structure for HMDB0015219 (Primaquine)

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