N4-(5-(3,4-dichlorophenylthio)-6-methoxyquinolin-8-yl)pentane-1,4-diamine hydrate

ID: ALA3245215

PubChem CID: 12409385

Max Phase: Preclinical

Molecular Formula: C21H25Cl2N3O2S

Molecular Weight: 436.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(NC(C)CCCN)c2ncccc2c1Sc1ccc(Cl)c(Cl)c1.O

Standard InChI:  InChI=1S/C21H23Cl2N3OS.H2O/c1-13(5-3-9-24)26-18-12-19(27-2)21(15-6-4-10-25-20(15)18)28-14-7-8-16(22)17(23)11-14;/h4,6-8,10-13,26H,3,5,9,24H2,1-2H3;1H2

Standard InChI Key:  YTCDPMYOZNSEJK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   26.7522   -5.0606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3983   -4.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3972   -5.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1119   -6.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1101   -4.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8256   -4.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8263   -5.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5417   -6.1882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2566   -5.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2519   -4.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5360   -4.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6837   -4.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6835   -3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1139   -7.0193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4004   -7.4335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4023   -8.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6850   -7.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1177   -8.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8312   -8.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5466   -8.6659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1077   -3.7163    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.8209   -3.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5345   -3.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2472   -3.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2452   -2.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5245   -2.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8147   -2.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9578   -2.0591    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.5191   -1.2395    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  2 12  1  0
 12 13  1  0
  4 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
  5 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
 26 29  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: 436.41

Molecular Weight (Monoisotopic): 435.0939

AlogP: 6.24

#Rotatable Bonds: 8

Polar Surface Area: 60.17

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 10.20

CX LogP: 5.04

CX LogD: 2.44

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -0.76

References

1. Tanabe K, Chen EH, Verma BL, Saggiomo AJ, Nodiff EA..  (1978)  Modifications of primiaquine as antimalarials. 2. 5-Phenylthio and 5-anilino derivatives of primaquine.,  21  (1): [PMID:412967] [10.1021/jm00199a028]

Source

Source(1):

• Scientific Literature