4-chloro-N-{2,2-dichloro-1-[N'-cyano-N''-(6-fluoropyridin-3-yl)guanidino]propyl}benzamide

ID: ALA238884

PubChem CID: 10297236

Max Phase: Preclinical

Molecular Formula: C17H14Cl3FN6O

Molecular Weight: 443.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1ccc(Cl)cc1)N/C(=N/C#N)Nc1ccc(F)nc1

Standard InChI:  InChI=1S/C17H14Cl3FN6O/c1-17(19,20)15(26-14(28)10-2-4-11(18)5-3-10)27-16(24-9-22)25-12-6-7-13(21)23-8-12/h2-8,15H,1H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  IYAGTYUXIZQQHR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   14.8277   -4.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8266   -5.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5414   -5.8985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2578   -5.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2550   -4.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5396   -4.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9679   -4.2395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6839   -4.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3968   -4.2341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6870   -5.4743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9741   -5.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2542   -6.2958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1128   -4.6439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8258   -4.2287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1159   -5.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1083   -6.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9409   -5.4712    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.2909   -5.4688    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.5418   -4.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2547   -4.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5449   -5.4635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9678   -4.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6803   -4.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6776   -3.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9566   -2.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2471   -3.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3900   -2.9788    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.1118   -5.8976    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
 24 27  1  0
  1  2  2  0
  2 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA238884

   4-chloro-N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[(6-fluoropyridin-3-yl)amino]methylidene]amino]propyl]benzamide

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: 443.70

Molecular Weight (Monoisotopic): 442.0279

AlogP: 3.66

#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: ┄

CX LogP: 4.14

CX LogD: 4.14

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.16

Np Likeness Score: -1.58

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