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

ID: ALA393952

PubChem CID: 23730969

Max Phase: Preclinical

Molecular Formula: C18H14Cl2F4N6O2

Molecular Weight: 493.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H14Cl2F4N6O2/c1-17(19,20)15(30-16(27-9-25)28-11-4-7-13(21)26-8-11)29-14(31)10-2-5-12(6-3-10)32-18(22,23)24/h2-8,15H,1H3,(H,29,31)(H2,27,28,30)

Standard InChI Key:  GRYFUKKPZZSJJK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.1681   -0.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1693   -1.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4544   -1.6694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7380   -1.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7409   -0.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562   -0.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0279   -0.0103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3119   -0.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5990   -0.0049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3088   -1.2451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0217   -1.6603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7417   -2.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1170   -0.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8299    0.0005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1201   -1.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451   -1.2420    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7049   -1.2397    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5459   -0.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2589    0.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5490   -1.2343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9720   -0.4061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6844    0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818    0.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9607    1.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2513    0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8841   -1.6684    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3941    1.2504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1107    0.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000    0.1260    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5214    1.5570    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.8252    0.4290    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
 13  9  1  0
  2 27  1  0
  1  2  2  0
 24 28  1  0
 13 14  1  0
 28 29  1  0
 29 32  1  0
 29 31  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA393952

   N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[(6-fluoropyridin-3-yl)amino]methylidene]amino]propyl]-4-(trifluoromethoxy)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: 493.25

Molecular Weight (Monoisotopic): 492.0491

AlogP: 3.91

#Rotatable Bonds: 6

Polar Surface Area: 111.43

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

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: 32

QED Weighted: 0.11

Np Likeness Score: -1.45

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