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

ID: ALA392290

PubChem CID: 10206849

Max Phase: Preclinical

Molecular Formula: C18H14Cl3F3N6O

Molecular Weight: 493.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1cccc(Cl)c1)N/C(=N/C#N)Nc1ccc(C(F)(F)F)nc1

Standard InChI:  InChI=1S/C18H14Cl3F3N6O/c1-17(20,21)15(29-14(31)10-3-2-4-11(19)7-10)30-16(27-9-25)28-12-5-6-13(26-8-12)18(22,23)24/h2-8,15H,1H3,(H,29,31)(H2,27,28,30)

Standard InChI Key:  GYZZBDLKKNZTQP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    7.0652  -17.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0641  -18.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7789  -18.8569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4953  -18.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4925  -17.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7771  -17.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2054  -17.1978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9214  -17.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6343  -17.1924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9245  -18.4326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2116  -18.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4917  -19.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3503  -17.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0633  -17.1870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3534  -18.4272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3458  -19.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1784  -18.4295    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.5284  -18.4272    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.7793  -17.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4922  -17.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7824  -18.4218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2053  -17.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9178  -17.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9151  -16.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1941  -15.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4846  -16.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493  -18.8559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292  -19.2625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.7581  -19.5725    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9422  -18.1383    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.6336  -17.5893    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  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
  2 27  1  0
  1  2  2  0
 27 28  1  0
 13 14  1  0
 27 29  1  0
  5  7  1  0
 27 30  1  0
 13 15  1  0
 23 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA392290

   3-chloro-N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[[6-(trifluoromethyl)pyridin-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: 493.70

Molecular Weight (Monoisotopic): 492.0247

AlogP: 4.54

#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: 4.86

CX LogD: 4.86

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.19

Np Likeness Score: -1.73

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