4-chloro-N-(2,2-dichloro-1-{[(E)-(cyanoimino)(pyridin-3-ylamino)methyl]amino}propyl)benzamide

ID: ALA1788243

PubChem CID: 54582951

Max Phase: Preclinical

Molecular Formula: C17H15Cl3N6O

Molecular Weight: 425.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)[C@H](NC(=O)c1ccc(Cl)cc1)N/C(=N/c1cccnc1)NC#N

Standard InChI:  InChI=1S/C17H15Cl3N6O/c1-17(19,20)15(25-14(27)11-4-6-12(18)7-5-11)26-16(23-10-21)24-13-3-2-8-22-9-13/h2-9,15H,1H3,(H,25,27)(H2,23,24,26)/t15-/m1/s1

Standard InChI Key:  VWXQCJYCNKGDEL-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.3167   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -0.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -0.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -1.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -0.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -0.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8875   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -1.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -1.7375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6000   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8792    0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4625   -1.6625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -1.6667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.3042    0.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875    1.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3125   -0.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0167    1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9625   -2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1667   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  1  1  0
  6  4  1  0
  7  5  1  0
  3  8  1  1
  9  7  3  0
 10  1  2  0
 11  6  1  0
 12  6  2  0
 13 24  2  0
 14 11  2  0
 15 11  1  0
 16  8  1  0
 17  8  1  0
 18 20  1  0
 19 10  1  0
 20 15  2  0
 21 14  1  0
 22 18  1  0
 23  8  1  0
 24 19  1  0
 25 27  2  0
 26 19  2  0
 27 26  1  0
 13 25  1  0
 18 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1788243

   4-chloro-N-[(1R)-2,2-dichloro-1-[(Z)-[(cyanoamino)-(pyridin-3-ylamino)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: 425.71

Molecular Weight (Monoisotopic): 424.0373

AlogP: 3.33

#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: 6.09

CX LogP: 3.28

CX LogD: 3.26

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.17

Np Likeness Score: -1.35

References

1. Perez-Medrano A, Buckner SA, Coghlan MJ, Gregg RJ, Gopalakrishnan M, Kort ME, Lynch JK, Scott VE, Sullivan JP, Whiteaker KL, Carroll WA..  (2004)  Design and synthesis of novel cyanoguanidine ATP-sensitive potassium channel openers for the treatment of overactive bladder.,  14  (2): [PMID:14698167] [10.1016/j.bmcl.2003.10.063]

Source

Source(1):

• Scientific Literature