N*9*-(4-Methylamino-phenyl)-acridine-3,9-diamine

ID: ALA34843

PubChem CID: 44283381

Max Phase: Preclinical

Molecular Formula: C20H18N4

Molecular Weight: 314.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1ccc(Nc2c3ccccc3nc3cc(N)ccc23)cc1

Standard InChI:  InChI=1S/C20H18N4/c1-22-14-7-9-15(10-8-14)23-20-16-4-2-3-5-18(16)24-19-12-13(21)6-11-17(19)20/h2-12,22H,21H2,1H3,(H,23,24)

Standard InChI Key:  RADZUHZYBGTFCL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    2.8500   -8.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -9.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -9.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8542  -10.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -9.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -9.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -7.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875  -10.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -8.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042   -9.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -7.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917   -9.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -6.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6917   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250  -10.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -7.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500   -6.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542   -6.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -7.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -8.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250  -10.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -9.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7125   -9.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  6  1  0
  5  1  1  0
  6  5  1  0
  7  1  1  0
  8  3  1  0
  9  2  1  0
 10 12  1  0
 11  7  1  0
 12  9  2  0
 13 18  1  0
 14 13  1  0
 15 10  1  0
 16 11  2  0
 17 11  1  0
 18 17  2  0
 19 16  1  0
 20  5  2  0
 21  6  2  0
 22 14  1  0
 23 20  1  0
 24 23  2  0
  3  4  2  0
 13 19  2  0
 24 21  1  0
 10  8  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA34843

   9-N-[4-(methylamino)phenyl]acridine-3,9-diamine

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: 314.39

Molecular Weight (Monoisotopic): 314.1531

AlogP: 4.76

#Rotatable Bonds: 3

Polar Surface Area: 62.97

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.60

CX LogP: 3.59

CX LogD: 1.99

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.38

Np Likeness Score: -0.56

References

1. Gamage SA, Tepsiri N, Wilairat P, Wojcik SJ, Figgitt DP, Ralph RK, Denny WA..  (1994)  Synthesis and in vitro evaluation of 9-anilino-3,6-diaminoacridines active against a multidrug-resistant strain of the malaria parasite Plasmodium falciparum.,  37  (10): [PMID:8182707] [10.1021/jm00036a014]

Source

Source(1):

• Scientific Literature