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

ID: ALA241198

PubChem CID: 23729814

Max Phase: Preclinical

Molecular Formula: C18H14BrCl2F3N6O

Molecular Weight: 538.16

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1ccc(Br)cc1)N/C(=N/C#N)Nc1ccc(C(F)(F)F)nc1

Standard InChI:  InChI=1S/C18H14BrCl2F3N6O/c1-17(20,21)15(29-14(31)10-2-4-11(19)5-3-10)30-16(27-9-25)28-12-6-7-13(26-8-12)18(22,23)24/h2-8,15H,1H3,(H,29,31)(H2,27,28,30)

Standard InChI Key:  JBZYQPVYNMFIDL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.0014  -26.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0026  -27.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2878  -28.1110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713  -27.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5742  -26.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896  -26.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8613  -26.4520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1453  -26.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4323  -26.4466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1421  -27.6868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551  -28.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5750  -28.5083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2837  -26.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966  -26.4412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2868  -27.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792  -28.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1118  -27.6837    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5382  -27.6813    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7126  -26.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4255  -26.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7157  -27.6760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1387  -26.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8511  -26.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484  -25.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1274  -25.1978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4179  -25.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7174  -28.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4375  -28.5167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3086  -28.8267    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1244  -27.3925    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608  -25.1913    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  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
 27 28  1  0
 13 14  1  0
 27 29  1  0
  5  7  1  0
 27 30  1  0
 13 15  1  0
 24 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA241198

   4-bromo-N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[[6-(trifluoromethyl)pyridin-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: 538.16

Molecular Weight (Monoisotopic): 535.9742

AlogP: 4.65

#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: ┄

CX Basic pKa: ┄

CX LogP: 5.03

CX LogD: 5.03

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.17

Np Likeness Score: -1.56

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