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

ID: ALA240989

PubChem CID: 23729716

Max Phase: Preclinical

Molecular Formula: C18H14Cl2F3IN6O

Molecular Weight: 585.16

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H14Cl2F3IN6O/c1-17(19,20)15(29-14(31)10-2-4-11(24)5-3-10)30-16(27-9-25)28-12-6-7-13(26-8-12)18(21,22)23/h2-8,15H,1H3,(H,29,31)(H2,27,28,30)

Standard InChI Key:  VARZTOUSNAUVDK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.7848  -22.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7859  -22.8440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0711  -23.2569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3547  -22.8435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3575  -22.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729  -21.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446  -21.5978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9286  -22.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2157  -21.5924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9255  -22.8326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6384  -23.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3583  -23.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5003  -22.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2133  -21.5870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034  -22.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4958  -23.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3284  -22.8295    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3216  -22.8272    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9293  -21.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6422  -21.5817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9324  -22.8218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3553  -21.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0678  -21.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0651  -20.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3441  -20.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6346  -20.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5007  -23.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2208  -23.6625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0919  -23.9725    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9078  -22.5383    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.7775  -20.3371    0.0000 I   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
 23 24  2  0
 11 12  3  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 26 20  1  0
 13  9  1  0
  2 27  1  0
  1  2  2  0
 27 28  1  0
 13 14  1  0
 27 29  1  0
  5  7  1  0
 27 30  1  0
 13 15  1  0
 24 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA240989

   N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[[6-(trifluoromethyl)pyridin-3-yl]amino]methylidene]amino]propyl]-4-iodobenzamide

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: 585.16

Molecular Weight (Monoisotopic): 583.9603

AlogP: 4.49

#Rotatable Bonds: 5

Polar Surface Area: 102.20

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.19

CX LogD: 5.19

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.12

Np Likeness Score: -1.72

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