3,5-dichloro-N-{2,2-dichloro-1-[N'-(6-chloropyridin-3-yl)-N''-cyanoguanidine]propyl}benzamide

ID: ALA239119

PubChem CID: 10117487

Max Phase: Preclinical

Molecular Formula: C17H13Cl5N6O

Molecular Weight: 494.60

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H13Cl5N6O/c1-17(21,22)15(27-14(29)9-4-10(18)6-11(19)5-9)28-16(25-8-23)26-12-2-3-13(20)24-7-12/h2-7,15H,1H3,(H,27,29)(H2,25,26,28)

Standard InChI Key:  BMPBNQOBXMEIAX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    4.6527    0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6516    0.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664   -0.3985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0828    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0800    0.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3646    1.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7929    1.2605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5089    0.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2218    1.2659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5120    0.0257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7991   -0.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -0.7958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9378    0.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6508    1.2713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9409    0.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9333   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7659    0.0288    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1159    0.0312    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.3668    0.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0797    1.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3699    0.0365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7928    0.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5053    1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5026    2.1051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7816    2.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0721    2.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9368   -0.3976    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.7755    3.3397    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.2211    0.8691    0.0000 Cl  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:

   

   ALA239119

   3,5-dichloro-N-[2,2-dichloro-1-[(Z)-[[(6-chloropyridin-3-yl)amino]-(cyanoamino)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: 494.60

Molecular Weight (Monoisotopic): 491.9593

AlogP: 4.83

#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: 13.99

CX Basic pKa: ┄

CX LogP: 5.03

CX LogD: 5.03

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.14

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