Acetic acid 1-[2-(4-ethylsulfanyl-3-methyl-pyridin-2-ylmethanesulfinyl)-benzoimidazol-1-yl]-ethyl ester

ID: ALA10013

PubChem CID: 14894172

Max Phase: Preclinical

Molecular Formula: C20H23N3O3S2

Molecular Weight: 417.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSc1ccnc(C[S+]([O-])c2nc3ccccc3n2C(C)OC(C)=O)c1C

Standard InChI:  InChI=1S/C20H23N3O3S2/c1-5-27-19-10-11-21-17(13(19)2)12-28(25)20-22-16-8-6-7-9-18(16)23(20)14(3)26-15(4)24/h6-11,14H,5,12H2,1-4H3

Standard InChI Key:  BANYVCVZKRCIQR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.2216   -4.2251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8932   -3.0602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4169   -2.9874    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6104   -4.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0341   -4.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511   -3.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6952   -3.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9762   -2.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7776   -5.5916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9846   -2.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664   -6.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2618   -3.4056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4123   -2.1561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2656   -1.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3734   -5.8922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2703   -0.9149    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5448   -2.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5454   -2.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8174   -4.5257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4593   -5.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7021   -1.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2787   -3.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408   -6.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5513   -0.5014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2869   -5.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5524    0.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6966   -4.3885    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  2  1  0
  7  3  1  0
  8  4  1  0
  9  8  1  0
 10  5  1  0
 11  9  1  0
 12 10  1  0
 13  9  2  0
 14  4  1  0
 15 11  2  0
 16 12  2  0
 17 15  1  0
 18 13  1  0
 19 18  2  0
 20  5  1  0
 21  6  2  0
 22 11  1  0
 23  7  2  0
 24 12  1  0
 25 17  1  0
 26 21  1  0
 27 25  1  0
 28 23  1  0
  6  7  1  0
 26 28  2  0
 19 15  1  0
M  CHG  2   4   1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA10013

   1-[2-[(4-Ethylsulfanyl-3-methylpyridin-2-yl)methylsulfinyl]benzimidazol-1-yl]ethyl 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: 417.56

Molecular Weight (Monoisotopic): 417.1181

AlogP: 4.24

#Rotatable Bonds: 7

Polar Surface Area: 80.07

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.12

CX Basic pKa: 2.86

CX LogP: 3.43

CX LogD: 3.43

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: -0.67

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. 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