1-(4-(Acridin-9-ylamino)phenyl)-3-(p-tolyl)thiourea

ID: ALA3754614

PubChem CID: 127027600

Max Phase: Preclinical

Molecular Formula: C27H22N4S

Molecular Weight: 434.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=S)Nc2ccc(Nc3c4ccccc4nc4ccccc34)cc2)cc1

Standard InChI:  InChI=1S/C27H22N4S/c1-18-10-12-20(13-11-18)29-27(32)30-21-16-14-19(15-17-21)28-26-22-6-2-4-8-24(22)31-25-9-5-3-7-23(25)26/h2-17H,1H3,(H,28,31)(H2,29,30,32)

Standard InChI Key:  PRTLOTIFUABFLU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -3.8968    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8968   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5002    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2806   -0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5978   -1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5978    1.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058    3.0010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2905    3.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869    5.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5840    6.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8849    5.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8887    3.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5915    3.0106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1844    6.0148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4849    5.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7844    6.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4858    4.0657    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0849    5.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3847    6.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6831    5.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6816    3.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3818    3.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0835    3.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7202    3.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3754614

   ---

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: 434.57

Molecular Weight (Monoisotopic): 434.1565

AlogP: 7.25

#Rotatable Bonds: 4

Polar Surface Area: 48.98

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.77

CX Basic pKa: 8.50

CX LogP: 7.49

CX LogD: 6.46

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.21

Np Likeness Score: -1.00

References

1. Medapi B, Meda N, Kulkarni P, Yogeeswari P, Sriram D..  (2016)  Development of acridine derivatives as selective Mycobacterium tuberculosis DNA gyrase inhibitors.,  24  (4): [PMID:26787274] [10.1016/j.bmc.2016.01.011]

Source

Source(1):

• Scientific Literature