thiophene-2-carboxylic acid {1-[N'-(5-bromopyridin-3-yl)-N''-cyanoguanidino]-2,2-dichloropropyl}amide

ID: ALA241409

PubChem CID: 23729817

Max Phase: Preclinical

Molecular Formula: C15H13BrCl2N6OS

Molecular Weight: 476.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(Cl)(Cl)C(NC(=O)c1cccs1)N/C(=N/C#N)Nc1cncc(Br)c1

Standard InChI:  InChI=1S/C15H13BrCl2N6OS/c1-15(17,18)13(23-12(25)11-3-2-4-26-11)24-14(21-8-19)22-10-5-9(16)6-20-7-10/h2-7,13H,1H3,(H,23,25)(H2,21,22,24)

Standard InChI Key:  CUZJDAHDTFOLNT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -3.9098   -8.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9109   -8.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1961   -9.3069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4797   -8.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4825   -8.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1979   -7.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7696   -7.6478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536   -8.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -7.6424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0505   -8.8826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634   -9.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833   -9.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3753   -8.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0883   -7.6370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3784   -8.8772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -9.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2034   -8.8795    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466   -8.8772    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8043   -8.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5172   -7.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8074   -8.8718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6243   -7.6543    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.2727   -7.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224   -7.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4072   -6.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6009   -6.8082    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
  1 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:

   

   ALA241409

   N-[1-[(Z)-[[(5-bromopyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dichloropropyl]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: 476.19

Molecular Weight (Monoisotopic): 473.9432

AlogP: 3.69

#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: 0.14

CX LogP: 3.68

CX LogD: 3.68

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.20

Np Likeness Score: -1.97

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