Acetic acid 2-(1-oxo-1,2,3,4-tetrahydro-1lambda*4*-thiopyrano[3,2-c]pyridin-5-ylmethylsulfanyl)-benzoimidazol-1-ylmethyl ester

ID: ALA10078

PubChem CID: 14894169

Max Phase: Preclinical

Molecular Formula: C19H19N3O3S2

Molecular Weight: 401.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OCn1c(SCc2nccc3c2CCC[S+]3[O-])nc2ccccc21

Standard InChI:  InChI=1S/C19H19N3O3S2/c1-13(23)25-12-22-17-7-3-2-6-15(17)21-19(22)26-11-16-14-5-4-10-27(24)18(14)8-9-20-16/h2-3,6-9H,4-5,10-12H2,1H3

Standard InChI Key:  HXAKXLAZDSOJHL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.8082   -7.1974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1368   -6.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634   -7.1973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4188   -2.9865    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5519   -7.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5933   -6.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1326   -3.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1399   -4.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7223   -7.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1378   -5.8818    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.2140   -7.4954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8538   -4.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9991   -7.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5728   -4.2235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4114   -2.1569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8569   -5.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1760   -6.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8600   -2.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5780   -3.3940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6997   -3.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4209   -4.6456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9662   -8.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3030   -8.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028   -4.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6198   -7.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5470   -9.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7133   -9.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  7  1  0
  5  1  1  0
  6  1  1  0
  7  8  2  0
  8 12  1  0
  9  5  1  0
 10  2  1  0
 11  6  1  0
 12 16  1  0
 13 11  1  0
 14 12  2  0
 15  4  1  0
 16 10  1  0
 17 13  2  0
 18 19  2  0
 19 14  1  0
 20 24  1  0
 21  8  1  0
 22  5  2  0
 23  9  2  0
 24 21  1  0
 25 13  1  0
 26 22  1  0
 27 26  2  0
  9  3  1  0
 27 23  1  0
 18  7  1  0
  4 20  1  0
M  CHG  2   4   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA10078

   [2-[(1-oxo-3,4-dihydro-2H-thiopyrano[3,2-c]pyridin-5-yl)methylsulfanyl]benzimidazol-1-yl]methyl acetate

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: 401.51

Molecular Weight (Monoisotopic): 401.0868

AlogP: 3.30

#Rotatable Bonds: 5

Polar Surface Area: 80.07

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.85

CX LogP: 2.30

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.37

Np Likeness Score: -0.89

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