2-(4-Ethylsulfanyl-3-methyl-pyridin-2-ylmethanesulfinyl)-1-(2-methoxy-ethoxymethyl)-1H-benzoimidazole

ID: ALA10264

PubChem CID: 14894192

Max Phase: Preclinical

Molecular Formula: C20H25N3O3S2

Molecular Weight: 419.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSc1ccnc(C[S+]([O-])c2nc3ccccc3n2COCCOC)c1C

Standard InChI:  InChI=1S/C20H25N3O3S2/c1-4-27-19-9-10-21-17(15(19)2)13-28(24)20-22-16-7-5-6-8-18(16)23(20)14-26-12-11-25-3/h5-10H,4,11-14H2,1-3H3

Standard InChI Key:  LLHQVBGILNZHPS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.2244   -4.2246    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8980   -3.0606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4142   -2.9858    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0373   -4.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4497   -3.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6966   -3.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9769   -2.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9841   -2.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6104   -4.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2630   -3.4094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4156   -2.1585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2643   -1.7492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2715   -0.9204    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5454   -2.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5411   -2.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7824   -5.5919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4672   -5.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6975   -1.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2847   -3.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7335   -7.5206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518   -0.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1683   -6.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440   -6.9613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9019   -8.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2950   -5.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5480    0.3270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7037   -4.3864    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  4  1  0
  8  7  1  0
  9  8  1  0
 10  2  1  0
 11  8  2  0
 12  4  1  0
 13  9  2  0
 14 13  1  0
 15 11  1  0
 16 15  2  0
 17 10  1  0
 18  5  2  0
 19  9  1  0
 20  6  2  0
 21 24  1  0
 22 14  1  0
 23 17  1  0
 24 23  1  0
 25 21  1  0
 26 18  1  0
 27 22  1  0
 28 20  1  0
  5  6  1  0
 26 28  2  0
 13 16  1  0
M  CHG  2   4   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA10264

   2-[(4-Ethylsulfanyl-3-methylpyridin-2-yl)methylsulfinyl]-1-(2-methoxyethoxymethyl)benzimidazole

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: 419.57

Molecular Weight (Monoisotopic): 419.1337

AlogP: 3.78

#Rotatable Bonds: 10

Polar Surface Area: 72.23

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.69

CX Basic pKa: 2.86

CX LogP: 3.36

CX LogD: 3.36

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.28

Np Likeness Score: -1.09

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