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

ID: ALA238854

PubChem CID: 23729929

Max Phase: Preclinical

Molecular Formula: C17H13Cl2F3N6O

Molecular Weight: 445.23

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H13Cl2F3N6O/c1-17(18,19)15(27-14(29)9-4-10(20)6-11(21)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:  DMXSCUUZLQQKNT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    6.3611  -27.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3599  -27.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0747  -28.2985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7912  -27.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7883  -27.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0729  -26.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5012  -26.6395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2172  -27.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9302  -26.6341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2203  -27.8743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5074  -28.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7875  -28.6958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6462  -27.0439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3591  -26.6287    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6493  -27.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6417  -28.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4743  -27.8712    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.8243  -27.8688    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.0751  -27.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7880  -26.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0782  -27.8635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5012  -27.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2136  -26.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2109  -25.7949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4899  -25.3853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7804  -25.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6451  -28.2976    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.4839  -24.5603    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.9294  -27.0309    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
 25 28  1  0
 13 14  1  0
 23 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA238854

   N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[(6-fluoropyridin-3-yl)amino]methylidene]amino]propyl]-3,5-difluorobenzamide

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: 445.23

Molecular Weight (Monoisotopic): 444.0480

AlogP: 3.29

#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: 13.55

CX Basic pKa: ┄

CX LogP: 3.82

CX LogD: 3.82

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.16

Np Likeness Score: -1.55

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