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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 16:21:53 UTC

Update Date

2021-09-26 23:11:33 UTC

HMDB ID

HMDB0256103

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pamaquine

Description

Pamaquine, also known as plasmoquine, 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. Based on a literature review a significant number of articles have been published on Pamaquine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Pamaquine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pamaquine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0256103
     RDKit          3D
Pamaquine
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.6607   -1.7971   -0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5620   -1.1095    0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155    0.2624    0.2567 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1279    0.9295    1.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9027    2.4042    1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6583    0.7798   -0.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2890    0.2657   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2478    0.5476   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1152   -0.0058   -0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0555   -1.5099   -0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0628    0.3967    0.3552 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484    0.1516    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9916   -0.4759   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3679   -0.7285   -0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9510   -1.3587   -1.9576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1457   -1.7700   -3.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2054   -0.3495    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6352    0.2835    1.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4846    0.6539    2.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9548    1.2788    3.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5999    1.5114    3.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7482    1.1601    2.4411 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2813    0.5401    1.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8269   -2.5340   -1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5837   -1.1498   -1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6254   -2.3546   -1.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9403   -1.7002    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5977   -1.1481    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1236    0.8124    2.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051    0.4792    2.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0461    2.9420    2.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6143    2.8179    0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8717    2.6038    1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3818    0.7752   -1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4895    1.8967   -0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2471   -0.8079   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219    0.7854   -2.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0984    1.6509   -0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841    0.1765    0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937    0.4612   -1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012   -2.0431   -0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -1.7664   -1.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296   -1.8785   -0.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823    0.9265    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4330   -0.8063   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239   -2.6676   -2.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8486   -2.0537   -3.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4667   -0.9722   -3.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2753   -0.5406    0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5435    0.4422    2.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5917    1.5816    4.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1691    2.0109    4.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 12  1  0
 23 18  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
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 13 45  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
M  END

  Mrv1652309112118222D          

 23 24  0  0  0  0            999 V2000
    3.9211    0.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7313    0.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2713    0.3671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1912   -0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0815    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6216   -0.1007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4317    0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9718   -0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7017   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7819   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3220   -1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0520   -1.8157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5921   -2.4393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4022   -2.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6722   -1.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1321   -0.8802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4824   -1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7524   -0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3220   -3.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5119   -3.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9718   -2.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2418   -1.9716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 13 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0256103

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN(CC)CCCC(C)NC1=C2N=CC=CC2=CC(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H29N3O/c1-5-22(6-2)12-8-9-15(3)21-18-14-17(23-4)13-16-10-7-11-20-19(16)18/h7,10-11,13-15,21H,5-6,8-9,12H2,1-4H3

> <INCHI_KEY>
QTQWMSOQOSJFBV-UHFFFAOYSA-N

> <FORMULA>
C19H29N3O

> <MOLECULAR_WEIGHT>
315.461

> <EXACT_MASS>
315.231062566

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.04524423983228

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[5-(diethylamino)pentan-2-yl]-6-methoxyquinolin-8-amine

> <ALOGPS_LOGP>
4.26

> <JCHEM_LOGP>
3.172165199333334

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.109131011430485

> <JCHEM_PKA_STRONGEST_BASIC>
10.32405013913061

> <JCHEM_POLAR_SURFACE_AREA>
37.39

> <JCHEM_REFRACTIVITY>
98.0814

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.19e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pamaquine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0256103
     RDKit          3D
Pamaquine
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.6607   -1.7971   -0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5620   -1.1095    0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155    0.2624    0.2567 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1279    0.9295    1.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9027    2.4042    1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6583    0.7798   -0.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2890    0.2657   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2478    0.5476   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1152   -0.0058   -0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0555   -1.5099   -0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0628    0.3967    0.3552 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484    0.1516    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9916   -0.4759   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3679   -0.7285   -0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9510   -1.3587   -1.9576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1457   -1.7700   -3.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2054   -0.3495    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6352    0.2835    1.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4846    0.6539    2.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9548    1.2788    3.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5999    1.5114    3.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7482    1.1601    2.4411 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2813    0.5401    1.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8269   -2.5340   -1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5837   -1.1498   -1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6254   -2.3546   -1.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9403   -1.7002    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5977   -1.1481    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1236    0.8124    2.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051    0.4792    2.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0461    2.9420    2.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6143    2.8179    0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8717    2.6038    1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3818    0.7752   -1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4895    1.8967   -0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2471   -0.8079   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219    0.7854   -2.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0984    1.6509   -0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841    0.1765    0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937    0.4612   -1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012   -2.0431   -0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -1.7664   -1.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296   -1.8785   -0.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823    0.9265    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4330   -0.8063   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239   -2.6676   -2.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8486   -2.0537   -3.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4667   -0.9722   -3.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2753   -0.5406    0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5435    0.4422    2.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5917    1.5816    4.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1691    2.0109    4.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 12  1  0
 23 18  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
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 13 45  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       7.319   1.558   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.832   1.849   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       9.840   0.685   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.824  -1.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.352   0.976   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.360  -0.188   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.873   0.103   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.881  -1.061   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.377  -2.516   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      16.393  -0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      17.401  -1.934   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.897  -3.389   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.905  -4.553   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.417  -4.262   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.922  -2.807   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      18.913  -1.643   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      21.434  -2.516   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      21.938  -1.061   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.401  -6.009   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.889  -6.300   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.881  -5.135   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      15.385  -3.680   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   14   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   13                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0256103
HETATM    1  C1  UNL     1       4.661  -1.797  -0.992  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.562  -1.109   0.328  1.00  0.00           C  
HETATM    3  N1  UNL     1       4.216   0.262   0.257  1.00  0.00           N  
HETATM    4  C3  UNL     1       4.128   0.930   1.490  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.903   2.404   1.334  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.658   0.780  -0.908  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.289   0.266  -1.277  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.248   0.548  -0.251  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.115  -0.006  -0.634  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.055  -1.510  -0.806  1.00  0.00           C  
HETATM   11  N2  UNL     1      -1.063   0.397   0.355  1.00  0.00           N  
HETATM   12  C10 UNL     1      -2.448   0.152   0.309  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.992  -0.476  -0.788  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.368  -0.728  -0.867  1.00  0.00           C  
HETATM   15  O1  UNL     1      -4.951  -1.359  -1.958  1.00  0.00           O  
HETATM   16  C13 UNL     1      -4.146  -1.770  -3.043  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.205  -0.350   0.161  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.635   0.284   1.260  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.485   0.654   2.275  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.955   1.279   3.373  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.600   1.511   3.419  1.00  0.00           C  
HETATM   22  N3  UNL     1      -2.748   1.160   2.441  1.00  0.00           N  
HETATM   23  C19 UNL     1      -3.281   0.540   1.354  1.00  0.00           C  
HETATM   24  H1  UNL     1       3.827  -2.534  -1.058  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.584  -1.150  -1.861  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.625  -2.355  -1.108  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.940  -1.700   1.033  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.598  -1.148   0.786  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.124   0.812   2.018  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.405   0.479   2.210  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.046   2.942   2.320  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.614   2.818   0.581  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.872   2.604   1.007  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.382   0.775  -1.748  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.489   1.897  -0.744  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.247  -0.808  -1.520  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.022   0.785  -2.246  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.098   1.651  -0.200  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.484   0.177   0.752  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.394   0.461  -1.599  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.901  -2.043  -0.329  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.075  -1.766  -1.882  1.00  0.00           H  
HETATM   43  H20 UNL     1       0.930  -1.878  -0.410  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.682   0.926   1.199  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.433  -0.806  -1.645  1.00  0.00           H  
HETATM   46  H23 UNL     1      -3.524  -2.668  -2.789  1.00  0.00           H  
HETATM   47  H24 UNL     1      -4.849  -2.054  -3.879  1.00  0.00           H  
HETATM   48  H25 UNL     1      -3.467  -0.972  -3.401  1.00  0.00           H  
HETATM   49  H26 UNL     1      -6.275  -0.541   0.112  1.00  0.00           H  
HETATM   50  H27 UNL     1      -6.543   0.442   2.181  1.00  0.00           H  
HETATM   51  H28 UNL     1      -5.592   1.582   4.184  1.00  0.00           H  
HETATM   52  H29 UNL     1      -3.169   2.011   4.296  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    6
CONECT    4    5   29   30
CONECT    5   31   32   33
CONECT    6    7   34   35
CONECT    7    8   36   37
CONECT    8    9   38   39
CONECT    9   10   11   40
CONECT   10   41   42   43
CONECT   11   12   44
CONECT   12   13   13   23
CONECT   13   14   45
CONECT   14   15   17   17
CONECT   15   16
CONECT   16   46   47   48
CONECT   17   18   49
CONECT   18   19   19   23
CONECT   19   20   50
CONECT   20   21   21   51
CONECT   21   22   52
CONECT   22   23   23
END

HMDB0256103
     RDKit          3D
Pamaquine
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.6607   -1.7971   -0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5620   -1.1095    0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2155    0.2624    0.2567 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1279    0.9295    1.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9027    2.4042    1.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6583    0.7798   -0.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2890    0.2657   -1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2478    0.5476   -0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1152   -0.0058   -0.6344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0555   -1.5099   -0.8058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0628    0.3967    0.3552 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484    0.1516    0.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9916   -0.4759   -0.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3679   -0.7285   -0.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9510   -1.3587   -1.9576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1457   -1.7700   -3.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2054   -0.3495    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6352    0.2835    1.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4846    0.6539    2.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9548    1.2788    3.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5999    1.5114    3.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7482    1.1601    2.4411 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2813    0.5401    1.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8269   -2.5340   -1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5837   -1.1498   -1.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6254   -2.3546   -1.1080 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9403   -1.7002    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5977   -1.1481    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1236    0.8124    2.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051    0.4792    2.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0461    2.9420    2.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6143    2.8179    0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8717    2.6038    1.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3818    0.7752   -1.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4895    1.8967   -0.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2471   -0.8079   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0219    0.7854   -2.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0984    1.6509   -0.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4841    0.1765    0.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937    0.4612   -1.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012   -2.0431   -0.3294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -1.7664   -1.8821 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9296   -1.8785   -0.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823    0.9265    1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4330   -0.8063   -1.6450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239   -2.6676   -2.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8486   -2.0537   -3.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4667   -0.9722   -3.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2753   -0.5406    0.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5435    0.4422    2.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5917    1.5816    4.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1691    2.0109    4.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 12  1  0
 23 18  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
  5 33  1  0
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
  8 38  1  0
  8 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 11 44  1  0
 13 45  1  0
 16 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 19 50  1  0
 20 51  1  0
 21 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Plasmoquine	Kegg
8-((4-(Diethylamino)-1-methylbutyl)amino)-6-methoxyquinoline	HMDB
Pamaquine monohydrochloride	HMDB
Pamaquine monohydroiodide	HMDB
Pamaquine, citrate (1:1)	HMDB
Plasmocide	HMDB

Chemical Formula

C₁₉H₂₉N₃O

Average Molecular Weight

315.461

Monoisotopic Molecular Weight

315.231062566

IUPAC Name

N-[5-(diethylamino)pentan-2-yl]-6-methoxyquinolin-8-amine

Traditional Name

pamaquine

CAS Registry Number

Not Available

SMILES

CCN(CC)CCCC(C)NC1=C2N=CC=CC2=CC(OC)=C1

InChI Identifier

InChI=1S/C19H29N3O/c1-5-22(6-2)12-8-9-15(3)21-18-14-17(23-4)13-16-10-7-11-20-19(16)18/h7,10-11,13-15,21H,5-6,8-9,12H2,1-4H3

InChI Key

QTQWMSOQOSJFBV-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
Tertiary aliphatic amine
Tertiary amine
Ether
Azacycle
Secondary amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.26	ALOGPS
logP	3.17	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	17.11	ChemAxon
pKa (Strongest Basic)	10.32	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.39 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	98.08 m³·mol⁻¹	ChemAxon
Polarizability	38.05 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	187.695	30932474
DeepCCS	[M-H]-	185.337	30932474
DeepCCS	[M-2H]-	218.224	30932474
DeepCCS	[M+Na]+	193.788	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pamaquine	CCN(CC)CCCC(C)NC1=C2N=CC=CC2=CC(OC)=C1	3441.9	Standard polar	33892256
Pamaquine	CCN(CC)CCCC(C)NC1=C2N=CC=CC2=CC(OC)=C1	2540.2	Standard non polar	33892256
Pamaquine	CCN(CC)CCCC(C)NC1=C2N=CC=CC2=CC(OC)=C1	2607.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pamaquine,1TMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC(OC)=CC2=CC=CN=C12)[Si](C)(C)C	2463.6	Semi standard non polar	33892256
Pamaquine,1TMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC(OC)=CC2=CC=CN=C12)[Si](C)(C)C	2591.6	Standard non polar	33892256
Pamaquine,1TMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC(OC)=CC2=CC=CN=C12)[Si](C)(C)C	3164.8	Standard polar	33892256
Pamaquine,1TBDMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC(OC)=CC2=CC=CN=C12)[Si](C)(C)C(C)(C)C	2700.4	Semi standard non polar	33892256
Pamaquine,1TBDMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC(OC)=CC2=CC=CN=C12)[Si](C)(C)C(C)(C)C	2828.8	Standard non polar	33892256
Pamaquine,1TBDMS,isomer #1	CCN(CC)CCCC(C)N(C1=CC(OC)=CC2=CC=CN=C12)[Si](C)(C)C(C)(C)C	3253.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pamaquine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-9343000000-3fd10ecfaddf94b7fc19	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pamaquine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9868

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pamaquine

METLIN ID

Not Available

PubChem Compound

10290

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Pamaquine (HMDB0256103)

MOL for HMDB0256103 (Pamaquine)

3D MOL for HMDB0256103 (Pamaquine)

3D SDF for HMDB0256103 (Pamaquine)

3D-SDF for HMDB0256103 (Pamaquine)

PDB for HMDB0256103 (Pamaquine)

3D PDB for HMDB0256103 (Pamaquine)

SMILES for HMDB0256103 (Pamaquine)

INCHI for HMDB0256103 (Pamaquine)

Structure for HMDB0256103 (Pamaquine)

3D Structure for HMDB0256103 (Pamaquine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra