primaquine dihydrochloride

ID: ALA3217110

PubChem CID: 46216762

Max Phase: Preclinical

Molecular Formula: C15H23Cl2N3O

Molecular Weight: 259.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(C)CCCN)c2ncccc2c1.Cl.Cl

Standard InChI:  InChI=1S/C15H21N3O.2ClH/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;2*1H

Standard InChI Key:  STKZOTIORLKRFH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 20  0  0  0  0  0  0  0  0999 V2000
    7.7082    3.3741    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9073    7.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042    5.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034    5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003    3.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6385    3.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474    8.0954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2995    2.9981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.4964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9326   -0.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2082    3.3741    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  0
  5  8  1  0
  9 10  2  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  2  0
  9 18  1  0
 13 18  1  0
 19 20  1  0
 15 19  1  0
  8 17  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 259.35

Molecular Weight (Monoisotopic): 259.1685

AlogP: 2.78

#Rotatable Bonds: 6

Polar Surface Area: 60.17

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.20

CX LogP: 1.64

CX LogD: -0.96

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.84

Np Likeness Score: -0.43

References

1. Loup C, Lelièvre J, Benoit-Vical F, Meunier B..  (2007)  Trioxaquines and heme-artemisinin adducts inhibit the in vitro formation of hemozoin better than chloroquine.,  51  (10): [PMID:17698628] [10.1128/aac.00239-07]

Source

Source(1):

• Scientific Literature