2-[5-Chloro-4-(2,2,3,3,3-pentafluoro-propoxy)-pyridin-2-ylmethanesulfinyl]-3H-thieno[3,4-d]imidazole

ID: ALA342389

PubChem CID: 15133679

Max Phase: Preclinical

Molecular Formula: C14H9ClF5N3O2S2

Molecular Weight: 445.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [O-][S+](Cc1cc(OCC(F)(F)C(F)(F)F)c(Cl)cn1)c1nc2cscc2[nH]1

Standard InChI:  InChI=1S/C14H9ClF5N3O2S2/c15-8-2-21-7(1-11(8)25-6-13(16,17)14(18,19)20)5-27(24)12-22-9-3-26-4-10(9)23-12/h1-4H,5-6H2,(H,22,23)

Standard InChI Key:  RUPLPXJXUFCIFU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    5.1886   -3.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5688   -3.9607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7776   -2.6300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3895   -3.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5171   -3.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6593   -2.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3683   -3.0847    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4394   -2.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5889   -3.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7138   -3.6101    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5369   -2.6157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0971   -2.0300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6735   -1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9530   -2.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1248   -4.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1763   -3.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3357   -2.8789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1201   -2.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7609   -2.9093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5166   -2.2672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4480   -1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7910   -3.4965    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1366   -1.9999    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5711   -3.7894    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5111   -2.1427    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0747   -2.4396    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.0326   -1.2701    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6 18  1  0
  7  1  1  0
  8  6  1  0
  9  7  1  0
 10 17  1  0
 11 16  2  0
 12 14  2  0
 13 11  1  0
 14  9  1  0
 15  4  2  0
 16 14  1  0
 17  5  2  0
 18 19  1  0
 19 11  1  0
 20  7  1  0
 21 12  1  0
 22  6  1  0
 23  6  1  0
 24  8  1  0
 25  8  1  0
 26  8  1  0
 27 13  1  0
  5  4  1  0
 15 10  1  0
 21 13  2  0
M  CHG  2   7   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA342389

   2-[[5-chloro-4-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl]methylsulfinyl]-1H-thieno[3,4-d]imidazole

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: 445.82

Molecular Weight (Monoisotopic): 444.9745

AlogP: 4.56

#Rotatable Bonds: 6

Polar Surface Area: 73.86

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.23

CX Basic pKa: 2.05

CX LogP: 3.60

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: -0.86

References

1. Weidmann K, Herling AW, Lang HJ, Scheunemann KH, Rippel R, Nimmesgern H, Scholl T, Bickel M, Metzger H..  (1992)  2-[(2-pyridylmethyl)sulfinyl]-1H-thieno[3,4-d]imidazoles. A novel class of gastric H+/K(+)-ATPase inhibitors.,  35  (3): [PMID:1310742] [10.1021/jm00081a004]

Source

Source(1):

• Scientific Literature