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

ID: ALA395175

PubChem CID: 23729616

Max Phase: Preclinical

Molecular Formula: C18H17Cl3N6O

Molecular Weight: 439.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(N/C(=N\C#N)NC(NC(=O)c2ccc(Cl)cc2)C(C)(Cl)Cl)cn1

Standard InChI:  InChI=1S/C18H17Cl3N6O/c1-11-3-8-14(9-23-11)25-17(24-10-22)27-16(18(2,20)21)26-15(28)12-4-6-13(19)7-5-12/h3-9,16H,1-2H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  WGDNJXFQVGXCPO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    5.3861  -11.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3849  -12.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0997  -12.5110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8162  -12.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8133  -11.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0979  -10.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5262  -10.8520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2422  -11.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9552  -10.8466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2454  -12.0868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5324  -12.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8125  -12.9083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6712  -11.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3841  -10.8412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6743  -12.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6667  -12.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4993  -12.0837    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8493  -12.0813    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.1001  -11.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8130  -10.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1032  -12.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5262  -11.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2386  -10.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2359  -10.0074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5149   -9.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8054  -10.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9483   -9.5913    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6701  -12.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  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
  9 13  1  0
 24 27  1  0
  1  2  2  0
  2 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA395175

   4-chloro-N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[(6-methylpyridin-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: 439.73

Molecular Weight (Monoisotopic): 438.0529

AlogP: 3.83

#Rotatable Bonds: 5

Polar Surface Area: 102.20

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.58

CX LogP: 3.73

CX LogD: 3.73

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.22

Np Likeness Score: -1.58

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