Isobutyric acid 2-(pyridin-2-ylmethanesulfinyl)-benzoimidazol-1-ylmethyl ester

ID: ALA275274

PubChem CID: 14877924

Max Phase: Preclinical

Molecular Formula: C18H19N3O3S

Molecular Weight: 357.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C(=O)OCn1c([S+]([O-])Cc2ccccn2)nc2ccccc21

Standard InChI:  InChI=1S/C18H19N3O3S/c1-13(2)17(22)24-12-21-16-9-4-3-8-15(16)20-18(21)25(23)11-14-7-5-6-10-19-14/h3-10,13H,11-12H2,1-2H3

Standard InChI Key:  FMCBCCHPAFLSNR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.1382   -3.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2218   -4.2254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8936   -3.0602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4169   -2.9874    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0346   -4.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105   -4.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4517   -3.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7777   -5.5923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1663   -6.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6950   -3.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -2.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612   -3.4057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3731   -5.8930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9758   -2.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408   -6.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4598   -5.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2795   -3.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5440   -2.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1267   -7.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7222   -7.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9842   -2.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2877   -5.1101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6975   -4.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5446   -2.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2650   -1.7453    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  2  1  0
  7  3  1  0
  8  6  1  0
  9  8  1  0
 10  4  1  0
 11  4  1  0
 12 14  2  0
 13  9  2  0
 14 10  1  0
 15  9  1  0
 16  5  2  0
 17  7  2  0
 18 12  1  0
 19 15  1  0
 20 15  1  0
 21 14  1  0
 22 16  1  0
 23 17  1  0
 24 25  1  0
 25 21  2  0
  5  7  1  0
 22 23  2  0
 24 18  2  0
M  CHG  2   4   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA275274

   [2-(Pyridin-2-ylmethylsulfinyl)benzimidazol-1-yl]methyl 2-methylpropanoate

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: 357.44

Molecular Weight (Monoisotopic): 357.1147

AlogP: 2.90

#Rotatable Bonds: 6

Polar Surface Area: 80.07

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.37

CX LogP: 3.05

CX LogD: 3.05

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: -0.80

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