1-(1-Ethoxy-ethyl)-2-(pyridin-2-ylmethanesulfinyl)-1H-benzoimidazole

ID: ALA9862

PubChem CID: 14894186

Max Phase: Preclinical

Molecular Formula: C17H19N3O2S

Molecular Weight: 329.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(C)n1c([S+]([O-])Cc2ccccn2)nc2ccccc21

Standard InChI:  InChI=1S/C17H19N3O2S/c1-3-22-13(2)20-16-10-5-4-9-15(16)19-17(20)23(21)12-14-8-6-7-11-18-14/h4-11,13H,3,12H2,1-2H3

Standard InChI Key:  MRFCICSWTRVKGF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    5.1340   -3.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -4.2232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8958   -3.0595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4197   -2.9889    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0351   -4.3946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4474   -3.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085   -4.7804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6950   -3.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4138   -2.1577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2618   -3.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9755   -2.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7805   -5.5902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4649   -5.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2822   -3.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8225   -4.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5443   -2.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9826   -2.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1666   -6.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2925   -5.1066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7011   -4.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3422   -6.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5400   -2.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2631   -1.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  1  0
  5  2  1  0
  6  3  1  0
  7  2  1  0
  8  4  1  0
  9  4  1  0
 10 11  2  0
 11  8  1  0
 12  7  1  0
 13  5  2  0
 14  6  2  0
 15  7  1  0
 16 10  1  0
 17 11  1  0
 18 12  1  0
 19 13  1  0
 20 14  1  0
 21 18  1  0
 22 23  1  0
 23 17  2  0
  5  6  1  0
 19 20  2  0
 22 16  2  0
M  CHG  2   4   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA9862

   1-(1-Ethoxy-ethyl)-2-(pyridin-2-ylmethanesulfinyl)-1H-benzoimidazole

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: 329.43

Molecular Weight (Monoisotopic): 329.1198

AlogP: 3.29

#Rotatable Bonds: 6

Polar Surface Area: 63.00

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.37

CX LogP: 2.60

CX LogD: 2.60

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.65

Np Likeness Score: -1.02

References

1. Sih JC, Im WB, Robert A, Graber DR, Blakeman DP..  (1991)  Studies on (H(+)-K+)-ATPase inhibitors of gastric acid secretion. Prodrugs of 2-[(2-pyridinylmethyl)sulfinyl]benzimidazole proton-pump inhibitors.,  34  (3): [PMID:1848293] [10.1021/jm00107a026]

Source

Source(1):

• Scientific Literature