4-chloro-N-{2,2-dichloro-1-[N'-cyano-N''-(2-fluorophenyl)-guanidino]propyl}benzamide

ID: ALA238699

PubChem CID: 10275180

Max Phase: Preclinical

Molecular Formula: C18H15Cl3FN5O

Molecular Weight: 442.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1ccc(Cl)cc1)N/C(=N/C#N)Nc1ccccc1F

Standard InChI:  InChI=1S/C18H15Cl3FN5O/c1-18(20,21)16(26-15(28)11-6-8-12(19)9-7-11)27-17(24-10-23)25-14-5-3-2-4-13(14)22/h2-9,16H,1H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  LMCBQWWZXUAFOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    8.9827  -22.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2623  -22.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5518  -22.5056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5605  -23.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2856  -23.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9931  -23.3149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2974  -24.5634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0172  -24.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7302  -24.5591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0204  -25.7993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3074  -26.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875  -26.6208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4462  -24.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1591  -24.5537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4493  -25.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4417  -26.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2743  -25.7962    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.6243  -25.7938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.8751  -24.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5880  -24.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8782  -25.7885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3012  -24.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0136  -24.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0109  -23.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2899  -23.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5804  -23.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7233  -23.3038    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8512  -23.7540    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
  4 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA238699

   4-chloro-N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-(2-fluoroanilino)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: 442.71

Molecular Weight (Monoisotopic): 441.0326

AlogP: 4.27

#Rotatable Bonds: 5

Polar Surface Area: 89.31

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.96

CX LogD: 4.96

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.21

Np Likeness Score: -1.57

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