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

ID: ALA393424

PubChem CID: 23729815

Max Phase: Preclinical

Molecular Formula: C17H14BrCl2FN6O

Molecular Weight: 488.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1ccc(F)cc1)N/C(=N/C#N)Nc1cncc(Br)c1

Standard InChI:  InChI=1S/C17H14BrCl2FN6O/c1-17(19,20)15(26-14(28)10-2-4-12(21)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:  UDRXKZNYAQAXAE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    6.0027    1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0016    0.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7164   -0.2110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4328    0.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4300    1.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7146    1.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1429    1.4480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8589    1.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5718    1.4534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8620    0.2132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1491   -0.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292   -0.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2878    1.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0008    1.4588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2909    0.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2833   -0.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1159    0.2163    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.4659    0.2187    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.7168    1.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4297    1.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7199    0.2240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1428    1.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8553    1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8526    2.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1316    2.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4221    2.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2882    1.4415    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.5650    2.7087    0.0000 F   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
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA393424

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

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: 488.15

Molecular Weight (Monoisotopic): 485.9774

AlogP: 3.77

#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: 3.91

CX LogD: 3.91

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.20

Np Likeness Score: -1.63

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