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

ID: ALA238639

PubChem CID: 23729928

Max Phase: Preclinical

Molecular Formula: C18H17Cl2FN6O

Molecular Weight: 423.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)NC(N/C(=N/C#N)Nc2ccc(F)nc2)C(C)(Cl)Cl)cc1

Standard InChI:  InChI=1S/C18H17Cl2FN6O/c1-11-3-5-12(6-4-11)15(28)26-16(18(2,19)20)27-17(24-10-22)25-13-7-8-14(21)23-9-13/h3-9,16H,1-2H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  IBNGTFCMPMCDET-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    5.6027  -22.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6016  -23.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3164  -23.4277    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0328  -23.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0300  -22.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3146  -21.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7429  -21.7686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4589  -22.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1718  -21.7633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4620  -23.0034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7491  -23.4186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292  -23.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8878  -22.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6008  -21.7579    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8909  -22.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8833  -23.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7159  -23.0003    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.0659  -22.9980    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.3168  -22.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0297  -21.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3199  -22.9927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7428  -22.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4553  -21.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4526  -20.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7316  -20.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0221  -20.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8868  -23.4268    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.1650  -20.5079    0.0000 C   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:

   

   ALA238639

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

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: 423.28

Molecular Weight (Monoisotopic): 422.0825

AlogP: 3.32

#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: 4.04

CX LogD: 4.04

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.17

Np Likeness Score: -1.52

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