4-chloro-N-{2,2-dichloro-1-[N'-cyano-N''-(6-methoxypyridin-3-yl)guanidino]propyl}benzamide

ID: ALA238487

PubChem CID: 23729617

Max Phase: Preclinical

Molecular Formula: C18H17Cl3N6O2

Molecular Weight: 455.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(N/C(=N\C#N)NC(NC(=O)c2ccc(Cl)cc2)C(C)(Cl)Cl)cn1

Standard InChI:  InChI=1S/C18H17Cl3N6O2/c1-18(20,21)16(26-15(28)11-3-5-12(19)6-4-11)27-17(24-10-22)25-13-7-8-14(29-2)23-9-13/h3-9,16H,1-2H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  OZFHVRJRMHPLEO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.2632  -22.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9836  -22.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6940  -22.9014    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6853  -23.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9602  -24.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2527  -23.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484  -24.9593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286  -25.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5157  -24.9549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2255  -26.1951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9384  -26.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6583  -27.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7997  -25.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0867  -24.9495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7966  -26.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8042  -27.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0284  -26.1920    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6216  -26.1897    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6293  -25.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3422  -24.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6324  -26.1843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0553  -25.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7678  -24.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7651  -24.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441  -23.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3346  -24.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4775  -23.6996    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9919  -21.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2816  -21.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0
 13 15  1  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 15 17  1  0
 15 18  1  0
  8  9  1  0
 14 19  1  0
  4  5  1  0
 19 20  1  0
  8 10  2  0
 19 21  2  0
  2  3  1  0
 20 22  2  0
 10 11  1  0
 22 23  1  0
  5  6  2  0
 23 24  2  0
 11 12  3  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 26 20  1  0
 13  9  1  0
 24 27  1  0
  1  2  2  0
  2 28  1  0
 13 14  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA238487

   4-chloro-N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[(6-methoxypyridin-3-yl)amino]methylidene]amino]propyl]benzamide

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: 455.73

Molecular Weight (Monoisotopic): 454.0479

AlogP: 3.53

#Rotatable Bonds: 6

Polar Surface Area: 111.43

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.20

Np Likeness Score: -1.68

References

1. Perez-Medrano A, Brune ME, Buckner SA, Coghlan MJ, Fey TA, Gopalakrishnan M, Gregg RJ, Kort ME, Scott VE, Sullivan JP, Whiteaker KL, Carroll WA..  (2007)  Structure-activity studies of novel cyanoguanidine ATP-sensitive potassium channel openers for the treatment of overactive bladder.,  50  (24): [PMID:17973362] [10.1021/jm7010194]

Source

Source(1):

• Scientific Literature