4-chloro-N-{2,2-dichloro-1-[N'-cyano-N''-(6-trifluoromethylpyridin-3-yl}guanidino]propyl)benzamide

ID: ALA239090

PubChem CID: 10185064

Max Phase: Preclinical

Molecular Formula: C18H14Cl3F3N6O

Molecular Weight: 493.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1ccc(Cl)cc1)N/C(=N/C#N)Nc1ccc(C(F)(F)F)nc1

Standard InChI:  InChI=1S/C18H14Cl3F3N6O/c1-17(20,21)15(29-14(31)10-2-4-11(19)5-3-10)30-16(27-9-25)28-12-6-7-13(26-8-12)18(22,23)24/h2-8,15H,1H3,(H,29,31)(H2,27,28,30)

Standard InChI Key:  ZHQVGMHYYBSAEE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.1984  -11.5982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4836  -12.0110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7672  -11.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4854  -10.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571  -10.3520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3411  -10.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3718  -10.3466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380  -11.5868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0509  -12.0020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7708  -12.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0878  -10.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8008  -10.3412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0909  -11.5814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0833  -12.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159  -11.5837    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2659  -11.5813    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5168  -10.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2297  -10.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5199  -11.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9428  -10.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6553  -10.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6526   -9.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9316   -9.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2221   -9.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3650   -9.0913    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.9132  -12.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6333  -12.4167    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5044  -12.7267    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3203  -11.2925    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
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 11 12  3  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 26 20  1  0
 13  9  1  0
 24 27  1  0
  1  2  2  0
  2 28  1  0
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 28 29  1  0
  5  7  1  0
 28 30  1  0
 13 15  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA239090

   4-chloro-N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[[6-(trifluoromethyl)pyridin-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: 493.70

Molecular Weight (Monoisotopic): 492.0247

AlogP: 4.54

#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: 4.86

CX LogD: 4.86

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.19

Np Likeness Score: -1.61

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