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

ID: ALA264214

Cas Number: 99499-40-8

PubChem CID: 65861

Max Phase: Phase

Molecular Formula: C16H17N3OS2

Molecular Weight: 331.47

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Disuprazole | Disuprazole|Disuprazole [INN]|99499-40-8|V81J4OO2OT|CHEMBL264214|Disuprazolum|Disuprozol|2-(((4-(Ethylthio)-3-methyl-2-pyridyl)methyl)sulfinyl)benzimidazole|Disuprazolum [Latin]|Disuprozol [Spanish]|UNII-V81J4OO2OT|Disuprazole, 99%|SCHEMBL1815548|DTXSID60869337|BDBM50009041|2-[(4-ethylsulfanyl-3-methylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole|NS00127072|Q27291649|2-(4-Ethylsulfanyl-3-methyl-pyridin-2-ylmethanesulfinyl)-1H-benzoimidazole|2-{[4-(Ethylsulfanyl)-3-methylpyridin-2-yShow More⌵

Canonical SMILES:  CCSc1ccnc(C[S+]([O-])c2nc3ccccc3[nH]2)c1C

Standard InChI:  InChI=1S/C16H17N3OS2/c1-3-21-15-8-9-17-14(11(15)2)10-22(20)16-18-12-6-4-5-7-13(12)19-16/h4-9H,3,10H2,1-2H3,(H,18,19)

Standard InChI Key:  YWQUFKJVMWHDSN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   10.4329   -9.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5209   -9.8608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1870   -8.6988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7130   -8.6257    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2845   -8.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0045   -9.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5761   -9.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3369  -10.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7496   -9.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2899   -7.8100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8604   -8.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7141   -7.8041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1478   -9.0489    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.5856   -7.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8573   -7.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5793   -9.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7506  -10.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5760   -9.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4320   -8.6387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7193   -9.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9874  -10.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5748  -10.7472    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  6  1  0
  6  4  1  0
  7  5  2  0
  8  2  1  0
  9  3  1  0
 10  5  1  0
 11  7  1  0
 12  4  1  0
 13 11  1  0
 14 10  2  0
 15 14  1  0
 16  7  1  0
 17  8  2  0
 18  9  2  0
 19 13  1  0
 20 19  1  0
 21 18  1  0
 22 17  1  0
  8  9  1  0
 22 21  2  0
 15 11  2  0
M  CHG  2   4   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA264214

   DISUPRAZOLE

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: 331.47

Molecular Weight (Monoisotopic): 331.0813

AlogP: 3.69

#Rotatable Bonds: 5

Polar Surface Area: 64.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.35

CX Basic pKa: 2.86

CX LogP: 3.12

CX LogD: 3.11

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.57

Np Likeness Score: -0.97

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

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names