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

ID: ALA393130

PubChem CID: 10185759

Max Phase: Preclinical

Molecular Formula: C19H16Cl3F3N6O

Molecular Weight: 507.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc(C(F)(F)F)ccc1N/C(=N\C#N)NC(NC(=O)c1ccc(Cl)cc1)C(C)(Cl)Cl

Standard InChI:  InChI=1S/C19H16Cl3F3N6O/c1-10-13(7-8-14(28-10)19(23,24)25)29-17(27-9-26)31-16(18(2,21)22)30-15(32)11-3-5-12(20)6-4-11/h3-8,16H,1-2H3,(H,30,32)(H2,27,29,31)

Standard InChI Key:  DRIGSZZSKHBNCR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    8.2327  -15.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5123  -15.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8018  -15.8722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8105  -16.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5356  -17.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2431  -16.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5474  -17.9301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2672  -18.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9802  -17.9258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2704  -19.1659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5574  -19.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8375  -19.9875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6962  -18.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4091  -17.9204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6993  -19.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6917  -19.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5243  -19.1628    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.8743  -19.1605    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.1251  -18.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8380  -17.9150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1282  -19.1552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5512  -18.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2636  -17.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2609  -17.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5399  -16.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8304  -17.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9733  -16.6704    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.1012  -17.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5040  -14.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4958  -13.8000    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.6790  -14.6351    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.3290  -14.6207    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
 24 27  1  0
  1  2  2  0
  4 28  1  0
 13 14  1  0
  2 29  1  0
  5  7  1  0
 29 30  1  0
 13 15  1  0
 29 31  1  0
  3  4  2  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA393130

   4-chloro-N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[[2-methyl-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: 507.73

Molecular Weight (Monoisotopic): 506.0403

AlogP: 4.85

#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: ┄

CX Basic pKa: ┄

CX LogP: 4.99

CX LogD: 4.99

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.18

Np Likeness Score: -1.46

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