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

ID: ALA241411

PubChem CID: 23729818

Max Phase: Preclinical

Molecular Formula: C17H13BrCl4N6O

Molecular Weight: 539.05

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1cc(Cl)cc(Cl)c1)N/C(=N/C#N)Nc1cncc(Br)c1

Standard InChI:  InChI=1S/C17H13BrCl4N6O/c1-17(21,22)15(27-14(29)9-2-11(19)5-12(20)3-9)28-16(25-8-23)26-13-4-10(18)6-24-7-13/h2-7,15H,1H3,(H,27,29)(H2,25,26,28)

Standard InChI Key:  PRSNOWVESGXSLO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -3.7889  -12.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7901  -13.3773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0753  -13.7902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3588  -13.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3617  -12.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0771  -12.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488  -12.1311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328  -12.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2198  -12.1258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9297  -13.3659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6426  -13.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3625  -14.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4962  -12.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2091  -12.1204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4993  -13.3606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917  -14.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3243  -13.3628    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3257  -13.3605    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9251  -12.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6380  -12.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9282  -13.3552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3512  -12.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0636  -12.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0609  -11.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3399  -10.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6304  -11.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5035  -12.1376    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.3339  -10.0520    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.7794  -12.5226    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  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
 13  9  1  0
  1 27  1  0
  1  2  2  0
 25 28  1  0
 13 14  1  0
 23 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA241411

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

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: 539.05

Molecular Weight (Monoisotopic): 535.9088

AlogP: 4.94

#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: 13.99

CX Basic pKa: 0.15

CX LogP: 4.97

CX LogD: 4.97

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.16

Np Likeness Score: -1.51

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