Benzoic acid 1-[2-(pyridin-2-ylmethanesulfinyl)-benzoimidazol-1-yl]-ethyl ester

ID: ALA276437

PubChem CID: 14894176

Max Phase: Preclinical

Molecular Formula: C22H19N3O3S

Molecular Weight: 405.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(OC(=O)c1ccccc1)n1c([S+]([O-])Cc2ccccn2)nc2ccccc21

Standard InChI:  InChI=1S/C22H19N3O3S/c1-16(28-21(26)17-9-3-2-4-10-17)25-20-13-6-5-12-19(20)24-22(25)29(27)15-18-11-7-8-14-23-18/h2-14,16H,15H2,1H3

Standard InChI Key:  XNXLQABJKJXONG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.2221   -4.2258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8940   -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
    4.6105   -4.7846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0351   -4.3985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7778   -5.5931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4523   -3.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1662   -6.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4123   -2.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2605   -3.4059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408   -6.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1274   -7.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7261   -7.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9838   -2.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2886   -5.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6986   -4.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5437   -2.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8954   -8.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3040   -8.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2643   -1.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6868   -8.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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 22 15  1  0
 23 17  1  0
 24 18  1  0
 25 28  1  0
 26 21  2  0
 27 20  1  0
 28 22  2  0
 29 26  1  0
  6  8  1  0
 23 24  2  0
 25 19  2  0
 29 27  2  0
M  CHG  2   4   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA276437

   Benzoic acid 1-[2-(pyridin-2-ylmethanesulfinyl)-benzoimidazol-1-yl]-ethyl ester

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: 405.48

Molecular Weight (Monoisotopic): 405.1147

AlogP: 4.11

#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: 2.36

CX LogP: 4.09

CX LogD: 4.09

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.36

Np Likeness Score: -0.84

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