4-chloro-N-{2,2-dichloro-1-[N'-cyano-N''-(5-methylpyridin-3-yl)-guanidino]propyl}benzamide

ID: ALA238883

PubChem CID: 23729615

Max Phase: Preclinical

Molecular Formula: C18H17Cl3N6O

Molecular Weight: 439.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cncc(N/C(=N\C#N)NC(NC(=O)c2ccc(Cl)cc2)C(C)(Cl)Cl)c1

Standard InChI:  InChI=1S/C18H17Cl3N6O/c1-11-7-14(9-23-8-11)25-17(24-10-22)27-16(18(2,20)21)26-15(28)12-3-5-13(19)6-4-12/h3-9,16H,1-2H3,(H,26,28)(H2,24,25,27)

Standard InChI Key:  ZVUCFQREWXMLCC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    5.2277   -5.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2266   -5.9982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414   -6.4110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6578   -5.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6550   -5.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9396   -4.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3679   -4.7520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0839   -5.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7968   -4.7466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0870   -5.9868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3741   -6.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6542   -6.8083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5128   -5.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2258   -4.7412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5159   -5.9814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5083   -6.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3409   -5.9837    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.6909   -5.9813    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.9418   -5.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6547   -4.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9449   -5.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3678   -5.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0803   -4.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0776   -3.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3566   -3.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6471   -3.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7900   -3.4913    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.5132   -4.7585    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
 24 27  1  0
  1  2  2  0
  1 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA238883

   4-chloro-N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[(5-methylpyridin-3-yl)amino]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: 439.73

Molecular Weight (Monoisotopic): 438.0529

AlogP: 3.83

#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: ┄

CX Basic pKa: 2.41

CX LogP: 4.11

CX LogD: 4.11

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.22

Np Likeness Score: -1.43

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