N4-(2-(2,4-dichlorobenzyloxy)-6-methoxyquinolin-8-yl)pentane-1,4-diamine maleate

ID: ALA3274183

PubChem CID: 90678562

Max Phase: Preclinical

Molecular Formula: C26H29Cl2N3O6

Molecular Weight: 434.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(C)CCCN)c2nc(OCc3ccc(Cl)cc3Cl)ccc2c1.O=C(O)/C=C\C(=O)O

Standard InChI:  InChI=1S/C22H25Cl2N3O2.C4H4O4/c1-14(4-3-9-25)26-20-12-18(28-2)10-15-6-8-21(27-22(15)20)29-13-16-5-7-17(23)11-19(16)24;5-3(6)1-2-4(7)8/h5-8,10-12,14,26H,3-4,9,13,25H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

Standard InChI Key:  MSNOQLAEBDHGTF-BTJKTKAUSA-N

Molfile:  

     RDKit          2D

 37 38  0  0  0  0  0  0  0  0999 V2000
   11.0196   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6071   -2.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7821   -2.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3696   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6071   -0.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8446   -1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5446   -1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7821   -0.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2985   -3.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2974   -3.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0121   -4.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0103   -2.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7257   -3.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7265   -3.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4417   -4.2632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1568   -3.8485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1521   -3.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4362   -2.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5839   -2.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5837   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8729   -4.2582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5857   -3.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3018   -4.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3003   -5.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0155   -5.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7294   -5.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7235   -4.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0076   -3.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0140   -5.0943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3005   -5.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3024   -6.3335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5851   -5.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8716   -5.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1562   -5.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4427   -5.5150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4459   -5.4791    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.0002   -3.0103    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  1  5  2  0
  1  6  1  0
  4  7  2  0
  4  8  1  0
  9 10  2  0
 10 11  1  0
 11 14  2  0
 13 12  2  0
 12  9  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  9 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 11 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 26 36  1  0
 28 37  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: 434.37

Molecular Weight (Monoisotopic): 433.1324

AlogP: 5.67

#Rotatable Bonds: 9

Polar Surface Area: 69.40

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.20

CX LogP: 5.01

CX LogD: 2.41

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -0.95

References

1. Shetty RV, Wetter WP, Blanton CD..  (1977)  Synthesis of 2-benzyloxy and 2-benzylthio analogues of primaquine as potential antimalarials.,  20  (10): [PMID:409843] [10.1021/jm00220a025]

Source

Source(1):

• Scientific Literature