(+)-4-Chloro-N-{(1S)-2,2-dichloro-1-[N'-(6-chloropyridin-3-yl)-N''-cyanoguanidino]propyl}benzamide

ID: ALA2110262

PubChem CID: 70693564

Max Phase: Preclinical

Molecular Formula: C17H14Cl4N6O

Molecular Weight: 460.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)[C@H](NC(=O)c1ccc(Cl)cc1)N/C(=N/C#N)Nc1ccc(Cl)nc1

Standard InChI:  InChI=1S/C17H14Cl4N6O/c1-17(20,21)15(26-14(28)10-2-4-11(18)5-3-10)27-16(24-9-22)25-12-6-7-13(19)23-8-12/h2-8,15H,1H3,(H,26,28)(H2,24,25,27)/t15-/m1/s1

Standard InChI Key:  NULKQOQUGAKMTR-OAHLLOKOSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   13.6361    1.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6349    0.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3497    0.2890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0662    0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0633    1.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3479    1.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7762    1.9480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4922    1.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2052    1.9534    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4954    0.7132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7824    0.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0625   -0.1083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9212    1.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6341    1.9588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8930    0.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9167   -0.1354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7493    0.7163    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.0993    0.7187    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.3501    1.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0630    1.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3532    0.7240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7762    1.5522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4886    1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4859    2.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7649    3.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0554    2.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1983    3.2087    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.9201    0.2899    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  5  7  1  0
 13 15  1  1
  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
  1  2  2  0
  2 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2110262

   4-chloro-N-[(1R)-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: 460.15

Molecular Weight (Monoisotopic): 457.9983

AlogP: 4.18

#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: ┄

CX LogP: 4.42

CX LogD: 4.42

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.16

Np Likeness Score: -1.55

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