3,5-dichloro-N-{2,2-dichloro-1-[N'-cyano-N''-(6-fluoropyridin-3-yl)guanidino]propyl}benzamide

ID: ALA238422

PubChem CID: 23729819

Max Phase: Preclinical

Molecular Formula: C17H13Cl4FN6O

Molecular Weight: 478.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1cc(Cl)cc(Cl)c1)N/C(=N/C#N)Nc1ccc(F)nc1

Standard InChI:  InChI=1S/C17H13Cl4FN6O/c1-17(20,21)15(27-14(29)9-4-10(18)6-11(19)5-9)28-16(25-8-23)26-12-2-3-13(22)24-7-12/h2-7,15H,1H3,(H,27,29)(H2,25,26,28)

Standard InChI Key:  HJJFENPUQDMNOP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.3848  -16.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3859  -17.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6711  -18.2235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547  -17.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575  -16.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6729  -16.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2446  -16.5645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5286  -16.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8157  -16.5591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5255  -17.7993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384  -18.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583  -18.6208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997  -16.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6133  -16.5537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966  -17.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1042  -18.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7284  -17.7962    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9216  -17.7938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3293  -16.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0422  -16.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3324  -17.7885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7553  -16.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4678  -16.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4651  -15.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441  -15.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0346  -15.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1007  -18.2226    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7380  -14.4853    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.1836  -16.9559    0.0000 Cl  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
 25 28  1  0
 13 14  1  0
 23 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA238422

   3,5-dichloro-N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[(6-fluoropyridin-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: 478.14

Molecular Weight (Monoisotopic): 475.9889

AlogP: 4.32

#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: 13.99

CX Basic pKa: ┄

CX LogP: 4.74

CX LogD: 4.74

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.15

Np Likeness Score: -1.59

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