4-(3,6-Diamino-acridin-9-ylamino)-N,N-dimethyl-benzenesulfonamide

ID: ALA287878

PubChem CID: 10046986

Max Phase: Preclinical

Molecular Formula: C21H21N5O2S

Molecular Weight: 407.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)S(=O)(=O)c1ccc(Nc2c3ccc(N)cc3nc3cc(N)ccc23)cc1

Standard InChI:  InChI=1S/C21H21N5O2S/c1-26(2)29(27,28)16-7-5-15(6-8-16)24-21-17-9-3-13(22)11-19(17)25-20-12-14(23)4-10-18(20)21/h3-12H,22-23H2,1-2H3,(H,24,25)

Standard InChI Key:  JRGOBMIUUAJJDR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.5292  -11.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375  -12.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2417  -11.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2500  -12.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8167  -12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5250  -10.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6542   -9.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1917   -8.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042  -12.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667  -12.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3667   -9.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3667   -7.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042  -11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9542  -11.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6625   -9.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9375   -8.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2375   -9.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917  -12.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6792  -12.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917  -11.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6750  -11.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4042  -12.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750  -12.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9500  -10.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6042   -7.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6042   -9.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  3  7  1  0
  4  2  2  0
  5  2  1  0
  6  4  1  0
  7  5  1  0
  8 19  1  0
  9  1  1  0
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 11  7  2  0
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 18  9  1  0
 19 27  1  0
 20 22  2  0
 21 23  1  0
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 23 16  2  0
 24 21  1  0
 25 20  1  0
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 27 18  2  0
 28 10  1  0
 29 10  1  0
 26 19  2  0
  6  3  2  0
 20 11  1  0
 21 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA287878

   4-[(3,6-diaminoacridin-9-yl)amino]-N,N-dimethylbenzenesulfonamide

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: 407.50

Molecular Weight (Monoisotopic): 407.1416

AlogP: 3.55

#Rotatable Bonds: 4

Polar Surface Area: 114.34

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.32

CX LogP: 2.34

CX LogD: 0.67

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.35

Np Likeness Score: -1.17

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