thiophene-2-carboxylic acid {2,2-dichloro-1-[N'-cyano-N''-(6-fluoropyridin-3-yl)guanidino]propyl}amide

ID: ALA436805

PubChem CID: 23729927

Max Phase: Preclinical

Molecular Formula: C15H13Cl2FN6OS

Molecular Weight: 415.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1cccs1)N/C(=N/C#N)Nc1ccc(F)nc1

Standard InChI:  InChI=1S/C15H13Cl2FN6OS/c1-15(16,17)13(23-12(25)10-3-2-6-26-10)24-14(21-8-19)22-9-4-5-11(18)20-7-9/h2-7,13H,1H3,(H,23,25)(H2,21,22,24)

Standard InChI Key:  LHSQFXKKQLNRFJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -4.3806  -21.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3818  -22.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6669  -22.9402    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9505  -22.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9534  -21.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6688  -21.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2404  -21.2811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5244  -21.6909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8115  -21.2758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5213  -22.5159    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342  -22.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9542  -23.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0955  -21.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6174  -21.2704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0924  -22.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1000  -23.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7326  -22.5128    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9174  -22.5105    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3334  -21.6802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464  -21.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3365  -22.5052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0966  -22.9393    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8018  -21.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3515  -20.9798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363  -20.2668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1301  -20.4415    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
 13  9  1  0
  1  2  2  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
  2 22  1  0
 20 23  2  0
 10 11  1  0
  5  6  2  0
 11 12  3  0
  6  1  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA436805

   N-[2,2-dichloro-1-[(Z)-[(cyanoamino)-[(6-fluoropyridin-3-yl)amino]methylidene]amino]propyl]thiophene-2-carboxamide

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: 415.28

Molecular Weight (Monoisotopic): 414.0233

AlogP: 3.07

#Rotatable Bonds: 5

Polar Surface Area: 102.20

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.44

CX LogD: 3.44

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.17

Np Likeness Score: -2.05

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