2-(Pyridin-2-ylmethanesulfinyl)-1H-benzoimidazole

ID: ALA9861

Cas Number: 57237-97-5

PubChem CID: 72171

Max Phase: Phase

Molecular Formula: C13H11N3OS

Molecular Weight: 257.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [O-][S+](Cc1ccccn1)c1nc2ccccc2[nH]1

Standard InChI:  InChI=1S/C13H11N3OS/c17-18(9-10-5-3-4-8-14-10)13-15-11-6-1-2-7-12(11)16-13/h1-8H,9H2,(H,15,16)

Standard InChI Key:  HBDKFZNDMVLSHM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
   10.3895   -9.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1232   -8.7197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4873   -9.8691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7156   -8.6514    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.6846   -9.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2783  -10.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9881   -8.9617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6126   -7.7154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4080  -10.2537    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8005   -9.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5244   -9.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7162  -10.7302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2125  -11.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0238  -10.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4205  -11.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5444  -10.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9616  -10.0005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7977  -10.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5  2  1  0
  6  3  1  0
  7  4  1  0
  8  4  1  0
  9 10  1  0
 10  7  1  0
 11  5  1  0
 12  6  1  0
 13  9  2  0
 14 10  2  0
 15 18  2  0
 16 12  2  0
 17 11  2  0
 18 14  1  0
  6  5  2  0
 16 17  1  0
 13 15  1  0
M  CHG  2   4   1   8  -1
M  END

Alternative Forms

1. Parent:

   

   ALA9861

   TIMOPRAZOLE

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 257.32

Molecular Weight (Monoisotopic): 257.0623

AlogP: 2.27

#Rotatable Bonds: 3

Polar Surface Area: 64.63

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.35

CX Basic pKa: 2.38

CX LogP: 1.72

CX LogD: 1.72

Aromatic Rings: 3

Heavy Atoms: 18

QED Weighted: 0.73

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]

2. Adelstein GW, Yen CH, Haack RA, Yu S, Gullikson G, Price DV, Anglin C, Decktor DL, Tsai H, Keith RH..  (1988)  Substituted 2-[(2-benzimidazolylsulfinyl)methyl]anilines as potential inhibitors of H+/K+ ATPase.,  31  (6): [PMID:2836591] [10.1021/jm00401a024]

3. Roy K, Pratim Roy P..  (2009)  Comparative chemometric modeling of cytochrome 3A4 inhibitory activity of structurally diverse compounds using stepwise MLR, FA-MLR, PLS, GFA, G/PLS and ANN techniques.,  44  (7): [PMID:19128860] [10.1016/j.ejmech.2008.12.004]

4. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

5. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(3):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names
• AstraZeneca Deposited Data