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

ID: ALA238855

PubChem CID: 23729930

Max Phase: Preclinical

Molecular Formula: C17H14Cl2F2N6O

Molecular Weight: 427.24

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H14Cl2F2N6O/c1-17(18,19)15(26-14(28)10-2-4-11(20)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:  NLIUYDBYWNIEBV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    7.3819   -0.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3807   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0956   -1.9069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8120   -1.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8091   -0.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0938   -0.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5221   -0.2478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2381   -0.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9510   -0.2424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2412   -1.4826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5283   -1.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8083   -2.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6670   -0.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3799   -0.2370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6701   -1.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6625   -2.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4951   -1.4795    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.8451   -1.4772    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.0959   -0.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8089   -0.2317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0990   -1.4718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5220   -0.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2344   -0.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2318    0.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5107    1.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8013    0.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6659   -1.9059    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.9441    1.0129    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
  2 27  1  0
  1  2  2  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA238855

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

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: 427.24

Molecular Weight (Monoisotopic): 426.0574

AlogP: 3.15

#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: 3.67

CX LogD: 3.67

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.17

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