N-{2,2-dichloro-1-[N'-(6-chloropyridin-3-yl)-N''-cyanoguanidino]propyl}-4-iodobenzamide

ID: ALA239121

PubChem CID: 23729618

Max Phase: Preclinical

Molecular Formula: C17H14Cl3IN6O

Molecular Weight: 551.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1ccc(I)cc1)N/C(=N/C#N)Nc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C17H14Cl3IN6O/c1-17(19,20)15(26-14(28)10-2-4-11(21)5-3-10)27-16(24-9-22)25-12-6-7-13(18)23-8-12/h2-8,15H,1H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  ZTOYQCCAUQSDAX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   13.9152    0.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9141   -0.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6289   -0.4944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3453   -0.0810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3425    0.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6271    1.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0554    1.1647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7714    0.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4843    1.1701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7745   -0.0701    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0616   -0.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3417   -0.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2003    0.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9133    1.1755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2034   -0.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1958   -0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0284   -0.0670    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.3784   -0.0647    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.6293    0.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3422    1.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6324   -0.0593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0553    0.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7678    1.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7651    2.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0441    2.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3346    2.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1993   -0.4934    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.4775    2.4254    0.0000 I   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
  2 27  1  0
  1  2  2  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA239121

   N-[2,2-dichloro-1-[(Z)-[[(6-chloropyridin-3-yl)amino]-(cyanoamino)methylidene]amino]propyl]-4-iodobenzamide

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: 551.60

Molecular Weight (Monoisotopic): 549.9339

AlogP: 4.13

#Rotatable Bonds: 5

Polar Surface Area: 102.20

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.75

CX LogD: 4.75

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.10

Np Likeness Score: -1.71

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