2-(4-Ethylsulfanyl-3-methyl-pyridin-2-ylmethanesulfinyl)-1-methylsulfanylmethyl-1H-benzoimidazole

ID: ALA273448

PubChem CID: 14894188

Max Phase: Preclinical

Molecular Formula: C18H21N3OS3

Molecular Weight: 391.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSc1ccnc(C[S+]([O-])c2nc3ccccc3n2CSC)c1C

Standard InChI:  InChI=1S/C18H21N3OS3/c1-4-24-17-9-10-19-15(13(17)2)11-25(22)18-20-14-7-5-6-8-16(14)21(18)12-23-3/h5-10H,4,11-12H2,1-3H3

Standard InChI Key:  NJDNYXISRUWZSD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.1358   -3.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2243   -4.2243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8977   -3.0605    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
    6.0369   -4.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4492   -3.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6968   -3.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9773   -2.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9844   -2.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6103   -4.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2635   -3.4093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4156   -2.1587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2648   -1.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -0.9208    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7823   -5.5913    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5460   -2.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5418   -2.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4668   -5.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6977   -1.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2840   -3.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5524   -0.5085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684   -6.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2943   -5.1077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486    0.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7029   -4.3860    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  3  1  0
  7  4  1  0
  8  7  1  0
  9  8  1  0
 10  2  1  0
 11  8  2  0
 12  4  1  0
 13  9  2  0
 14 13  1  0
 15 10  1  0
 16 11  1  0
 17 16  2  0
 18  5  2  0
 19  9  1  0
 20  6  2  0
 21 14  1  0
 22 15  1  0
 23 18  1  0
 24 21  1  0
 25 20  1  0
  5  6  1  0
 23 25  2  0
 17 13  1  0
M  CHG  2   4   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA273448

   2-[(4-Ethylsulfanyl-3-methylpyridin-2-yl)methylsulfinyl]-1-(methylsulfanylmethyl)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: 391.59

Molecular Weight (Monoisotopic): 391.0847

AlogP: 4.48

#Rotatable Bonds: 7

Polar Surface Area: 53.77

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.08

CX Basic pKa: 2.86

CX LogP: 4.04

CX LogD: 4.04

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.44

Np Likeness Score: -1.11

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