2,2-Dimethyl-propionic acid 1-[2-(pyridin-2-ylmethanesulfinyl)-benzoimidazol-1-yl]-ethyl ester

ID: ALA10186

PubChem CID: 14894179

Max Phase: Preclinical

Molecular Formula: C20H23N3O3S

Molecular Weight: 385.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(OC(=O)C(C)(C)C)n1c([S+]([O-])Cc2ccccn2)nc2ccccc21

Standard InChI:  InChI=1S/C20H23N3O3S/c1-14(26-18(24)20(2,3)4)23-17-11-6-5-10-16(17)22-19(23)27(25)13-15-9-7-8-12-21-15/h5-12,14H,13H2,1-4H3

Standard InChI Key:  FSWZCSXRAFQNMV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.2218   -4.2253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8934   -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
    4.6104   -4.7839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0344   -4.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7777   -5.5921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4515   -3.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1663   -6.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951   -3.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408   -6.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -2.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732   -5.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614   -3.4057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760   -2.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2793   -3.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1271   -7.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7222   -7.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0778   -6.5818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5443   -2.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9843   -2.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2875   -5.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6973   -4.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449   -2.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2652   -1.7454    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
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  6  2  1  0
  7  5  1  0
  8  3  1  0
  9  7  1  0
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 19 11  1  0
 20 11  1  0
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 25 18  1  0
 26 27  1  0
 27 23  2  0
  6  8  1  0
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 26 22  2  0
M  CHG  2   4   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA10186

   1-[2-(Pyridin-2-ylmethylsulfinyl)benzimidazol-1-yl]ethyl 2,2-dimethylpropanoate

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: 385.49

Molecular Weight (Monoisotopic): 385.1460

AlogP: 3.85

#Rotatable Bonds: 5

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: 2.36

CX LogP: 3.84

CX LogD: 3.84

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.49

Np Likeness Score: -0.86

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]

2. 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