2-(4-Ethylsulfanyl-3-methyl-pyridin-2-ylmethylsulfanyl)-1-oxiranylmethyl-1H-benzoimidazole

ID: ALA10398

PubChem CID: 14894181

Max Phase: Preclinical

Molecular Formula: C19H21N3OS2

Molecular Weight: 371.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSc1ccnc(CSc2nc3ccccc3n2CC2CO2)c1C

Standard InChI:  InChI=1S/C19H21N3OS2/c1-3-24-18-8-9-20-16(13(18)2)12-25-19-21-15-6-4-5-7-17(15)22(19)10-14-11-23-14/h4-9,14H,3,10-12H2,1-2H3

Standard InChI Key:  NTNRWIWTWRPVPG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    1.1417   -2.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -1.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3542   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3500   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0667   -4.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417   -1.9167    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4000   -3.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875   -4.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -2.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -3.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3167   -1.1792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3375   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417   -1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833   -2.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833   -1.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  1  0
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  6  7  1  0
  7 10  1  0
  8  1  1  0
  9 12  1  0
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 13 12  2  0
 14  9  2  0
 15  8  1  0
 16 14  1  0
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 18 17  2  0
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 20  9  1  0
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 22 16  1  0
 23 19  1  0
 24 22  1  0
 25 21  1  0
  4  5  1  0
 23 25  2  0
  6 11  1  0
 18 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA10398

   2-[(4-Ethylsulfanyl-3-methylpyridin-2-yl)methylsulfanyl]-1-(oxiran-2-ylmethyl)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: 371.53

Molecular Weight (Monoisotopic): 371.1126

AlogP: 4.54

#Rotatable Bonds: 7

Polar Surface Area: 43.24

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.81

CX LogP: 4.31

CX LogD: 4.31

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.45

Np Likeness Score: -1.58

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