N-{1-[N'-(5-bromopyridin-3-yl)-N''-cyanoguanidino]-2,2-dichloropropyl}-4 -chlorobenzamide

ID: ALA393831

PubChem CID: 23730737

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)c1ccc(Cl)cc1)N/C(=N/C#N)Nc1cncc(Br)c1

Standard InChI:  InChI=1S/C17H14BrCl3N6O/c1-17(20,21)15(26-14(28)10-2-4-12(19)5-3-10)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:  SHZNAGUIFICORA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -4.5223   -4.9708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5234   -5.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8086   -6.2110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0922   -5.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950   -4.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8104   -4.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821   -4.5520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6661   -4.9618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9532   -4.5466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6630   -5.7868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3759   -6.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0958   -6.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2372   -4.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4758   -4.5412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341   -5.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2417   -6.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5909   -5.7837    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0591   -5.7813    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.1918   -4.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9047   -4.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1949   -5.7760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178   -4.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3303   -4.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3276   -3.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6066   -3.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8971   -3.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400   -3.2913    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.2368   -4.5585    0.0000 Br  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
  1 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA393831

   N-[1-[(Z)-[[(5-bromopyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dichloropropyl]-4-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: -1.52

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