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

ID: ALA393425

PubChem CID: 23730965

Max Phase: Preclinical

Molecular Formula: C18H17BrCl2N6O

Molecular Weight: 484.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C(=O)NC(N/C(=N/C#N)Nc2cncc(Br)c2)C(C)(Cl)Cl)cc1

Standard InChI:  InChI=1S/C18H17BrCl2N6O/c1-11-3-5-12(6-4-11)15(28)26-16(18(2,20)21)27-17(24-10-22)25-14-7-13(19)8-23-9-14/h3-9,16H,1-2H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  FLIFGOWGEVOLHM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    6.4319   -3.9291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4307   -4.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1456   -5.1694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8620   -4.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8591   -3.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1438   -3.5164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5721   -3.5103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0010   -3.5049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2912   -4.7451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5783   -5.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8583   -5.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7170   -3.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4299   -3.4995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7201   -4.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7125   -5.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5451   -4.7420    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.8951   -4.7397    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.1459   -3.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8589   -3.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1490   -4.7343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5720   -3.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2844   -3.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2818   -2.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5607   -2.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8513   -2.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7173   -3.5168    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.9941   -2.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  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
  9 13  1  0
  1 27  1  0
  1  2  2  0
 24 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA393425

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

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: 484.19

Molecular Weight (Monoisotopic): 482.0024

AlogP: 3.94

#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: ┄

CX Basic pKa: 0.15

CX LogP: 4.28

CX LogD: 4.28

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.20

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