N-{1-[N'-(5-Bromopyridin-3-yl)-N''-cyanoguanidino]-2,2-dichloropropyl}-3,5-difluorobenzamide

ID: ALA241200

PubChem CID: 23729816

Max Phase: Preclinical

Molecular Formula: C17H13BrCl2F2N6O

Molecular Weight: 506.14

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)Nc1cncc(Br)c1

Standard InChI:  InChI=1S/C17H13BrCl2F2N6O/c1-17(19,20)15(27-14(29)9-2-11(21)5-12(22)3-9)28-16(25-8-23)26-13-4-10(18)6-24-7-13/h2-7,15H,1H3,(H,27,29)(H2,25,26,28)

Standard InChI Key:  LGHXAJGIOQWBJH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -4.0514   -3.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0526   -4.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3378   -5.2235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6213   -4.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6242   -3.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3396   -3.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9113   -3.5645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1953   -3.9743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4823   -3.5591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1922   -4.7993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9051   -5.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250   -5.6208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337   -3.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9466   -3.5537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2368   -4.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -5.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618   -4.7962    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5882   -4.7938    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6626   -3.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755   -3.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657   -4.7885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0887   -3.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8011   -3.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7984   -2.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0774   -2.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3679   -2.7271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7660   -3.5710    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0714   -1.4853    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5169   -3.9559    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
  1 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:

   

   ALA241200

   N-[1-[(Z)-[[(5-bromopyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dichloropropyl]-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: 506.14

Molecular Weight (Monoisotopic): 503.9679

AlogP: 3.91

#Rotatable Bonds: 5

Polar Surface Area: 102.20

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.55

CX Basic pKa: 0.15

CX LogP: 4.05

CX LogD: 4.05

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.19

Np Likeness Score: -1.60

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