1-(1-Ethoxy-ethyl)-2-(4-ethylsulfanyl-3-methyl-pyridin-2-ylmethanesulfinyl)-1H-benzoimidazole

ID: ALA268465

Cas Number: 103335-00-8

PubChem CID: 14877919

Max Phase: Preclinical

Molecular Formula: C20H25N3O2S2

Molecular Weight: 403.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(C)n1c([S+]([O-])Cc2nccc(SCC)c2C)nc2ccccc21

Standard InChI:  InChI=1S/C20H25N3O2S2/c1-5-25-15(4)23-18-10-8-7-9-16(18)22-20(23)27(24)13-17-14(3)19(26-6-2)11-12-21-17/h7-12,15H,5-6,13H2,1-4H3

Standard InChI Key:  VYXDDSWGPLBVOZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.2244   -4.2244    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8979   -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
    6.0371   -4.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4495   -3.6762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6967   -3.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9842   -2.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6104   -4.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2632   -3.4093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4156   -2.1586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2645   -1.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2717   -0.9206    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5456   -2.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8243   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5520   -0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684   -6.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2947   -5.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5482    0.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7034   -4.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3440   -6.9609    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  3  1  0
  7  4  1  0
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  9  8  1  0
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 20  6  2  0
 21 10  1  0
 22 14  1  0
 23 17  1  0
 24 18  1  0
 25 22  1  0
 26 20  1  0
 27 23  1  0
  5  6  1  0
 24 26  2  0
 16 13  1  0
M  CHG  2   4   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA268465

   1-(1-Ethoxy-ethyl)-2-(4-ethylsulfanyl-3-methyl-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: 403.57

Molecular Weight (Monoisotopic): 403.1388

AlogP: 4.71

#Rotatable Bonds: 8

Polar Surface Area: 63.00

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.68

CX Basic pKa: 2.86

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.40

Np Likeness Score: -0.92

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