N-{1-[N'-(5-bromopyridin-3-yl)-N''-cyanoguanidino]-2,2-dichloropropyl}-3-methylbenzamide

ID: ALA241410

PubChem CID: 23730966

Max Phase: Preclinical

Molecular Formula: C18H17BrCl2N6O

Molecular Weight: 484.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C(=O)NC(N/C(=N/C#N)Nc2cncc(Br)c2)C(C)(Cl)Cl)c1

Standard InChI:  InChI=1S/C18H17BrCl2N6O/c1-11-4-3-5-12(6-11)15(28)26-16(18(2,20)21)27-17(24-10-22)25-14-7-13(19)8-23-9-14/h3-9,16H,1-2H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  IHSSYKVCEBDMQG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    7.1944   -8.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1932   -9.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9081   -9.9152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6245   -9.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6216   -8.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9063   -8.2622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3346   -8.2561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0506   -8.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7635   -8.2508    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0537   -9.4909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3408   -9.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6208  -10.3125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4795   -8.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1924   -8.2454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4826   -9.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4750  -10.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3076   -9.4878    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.6576   -9.4855    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.9084   -8.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6214   -8.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9115   -9.4802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3345   -8.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0469   -8.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0443   -7.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3232   -7.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6138   -7.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4798   -8.2626    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.3172   -6.1770    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
  1 27  1  0
  1  2  2  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA241410

   N-[1-[(Z)-[[(5-bromopyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dichloropropyl]-3-methylbenzamide

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: 484.19

Molecular Weight (Monoisotopic): 482.0024

AlogP: 3.94

#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: 0.15

CX LogP: 4.28

CX LogD: 4.28

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.20

Np Likeness Score: -1.60

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