N-{1-[N'-(5-bromopyridin-3-yl)-N''-cyanoguanidino]-2,2-dichloropropyl}-4-trifluoromethoxybenzamide

ID: ALA392291

PubChem CID: 23730967

Max Phase: Preclinical

Molecular Formula: C18H14BrCl2F3N6O2

Molecular Weight: 554.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1ccc(OC(F)(F)F)cc1)N/C(=N/C#N)Nc1cncc(Br)c1

Standard InChI:  InChI=1S/C18H14BrCl2F3N6O2/c1-17(20,21)15(30-16(27-9-25)28-12-6-11(19)7-26-8-12)29-14(31)10-2-4-13(5-3-10)32-18(22,23)24/h2-8,15H,1H3,(H,29,31)(H2,27,28,30)

Standard InChI Key:  URJHGIRONSZPOI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    6.4569  -13.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4557  -14.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1706  -14.9569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8870  -14.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8841  -13.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1687  -13.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5971  -13.2978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3131  -13.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0260  -13.2924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3162  -14.5326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6033  -14.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8833  -15.3542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7420  -13.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4549  -13.2870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7451  -14.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7375  -15.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5701  -14.5295    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.9201  -14.5272    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.1709  -13.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8839  -13.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1740  -14.5218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5970  -13.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3094  -13.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3068  -12.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5857  -12.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8763  -12.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7423  -13.3043    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.0191  -12.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7357  -12.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4458  -12.8583    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.1473  -11.7310    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.3275  -13.1629    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
 24 28  1  0
 13 14  1  0
 28 29  1  0
  5  7  1  0
 29 30  1  0
 13 15  1  0
 29 31  1  0
  3  4  2  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA392291

   N-[1-[(Z)-[[(5-bromopyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dichloropropyl]-4-(trifluoromethoxy)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: 554.15

Molecular Weight (Monoisotopic): 551.9691

AlogP: 4.53

#Rotatable Bonds: 6

Polar Surface Area: 111.43

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.15

CX LogP: 5.19

CX LogD: 5.19

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.16

Np Likeness Score: -1.45

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