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

ID: ALA238640

PubChem CID: 23730968

Max Phase: Preclinical

Molecular Formula: C18H17Cl2FN6O

Molecular Weight: 423.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(C(=O)NC(N/C(=N/C#N)Nc2ccc(F)nc2)C(C)(Cl)Cl)c1

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

Standard InChI Key:  FPLPBYRFXXEWSG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -4.4056  -26.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4068  -27.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919  -27.6402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9755  -27.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9784  -26.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6938  -25.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2654  -25.9811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5494  -26.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8365  -25.9758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463  -27.2159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592  -27.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9792  -28.0375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205  -26.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5924  -25.9704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1174  -27.2106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250  -28.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076  -27.2128    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9424  -27.2105    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3084  -26.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0214  -25.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115  -27.2052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7345  -26.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4469  -25.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4443  -25.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232  -24.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0138  -25.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216  -27.6393    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7172  -23.9020    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
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA238640

   N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[(6-fluoropyridin-3-yl)amino]methylidene]amino]propyl]-3-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: -1.67

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