N-{1-[N'-(5-bromopyridin-3-yl)-N''-cyanoguanidino]-2,2-dichloro-propyl}-3-chlorobenzamide

ID: ALA241199

PubChem CID: 23730853

Max Phase: Preclinical

Molecular Formula: C17H14BrCl3N6O

Molecular Weight: 504.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1cccc(Cl)c1)N/C(=N/C#N)Nc1cncc(Br)c1

Standard InChI:  InChI=1S/C17H14BrCl3N6O/c1-17(20,21)15(26-14(28)10-3-2-4-12(19)5-10)27-16(24-9-22)25-13-6-11(18)7-23-8-13/h2-8,15H,1H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  BPBHPPHRTXMKOI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -3.5889    0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5901   -0.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8753   -0.5860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1588   -0.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1617    0.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8771    1.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4488    1.0730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328    0.6632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0198    1.0784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7297   -0.1618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4426   -0.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1625   -0.9833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6962    0.6686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4091    1.0838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6993   -0.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6917   -0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243   -0.1587    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1257   -0.1563    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1251    0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8380    1.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1282   -0.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5512    0.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2636    1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2609    1.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5399    2.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8304    1.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3035    1.0665    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.5339    3.1522    0.0000 Cl  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:

   

   ALA241199

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

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: 504.60

Molecular Weight (Monoisotopic): 501.9478

AlogP: 4.29

#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: 0.15

CX LogP: 4.37

CX LogD: 4.37

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.19

Np Likeness Score: -1.64

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