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

ID: ALA239512

PubChem CID: 44436328

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/C#N)Nc1cccnc1

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-/m0/s1

Standard InChI Key:  VWXQCJYCNKGDEL-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  1  0  0  0  0  0999 V2000
    3.6861    0.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6849   -0.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3997   -0.4319    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1162   -0.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133    0.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3979    1.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8262    1.2272    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5422    0.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    1.2326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5454   -0.0076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8324   -0.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -0.8292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9712    0.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6841    1.2380    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9743   -0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7993   -0.0045    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.1493   -0.0022    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.4001    0.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1130    1.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4032    0.0032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8262    0.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5386    1.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5359    2.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8149    2.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1054    2.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2483    2.4879    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 13 14  1  0
  5  7  1  0
 13 15  1  6
  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
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA239512

   4-chloro-N-[(1S)-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: 3.52

#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: 1.89

CX LogP: 3.60

CX LogD: 3.60

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.22

Np Likeness Score: -1.53

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]

2. 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