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

ID: ALA9842

PubChem CID: 14894184

Max Phase: Preclinical

Molecular Formula: C23H30N4OS2

Molecular Weight: 442.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCSc1ccnc(C[S+]([O-])c2nc3ccccc3n2CCN2CCCCC2)c1C

Standard InChI:  InChI=1S/C23H30N4OS2/c1-3-29-22-11-12-24-20(18(22)2)17-30(28)23-25-19-9-5-6-10-21(19)27(23)16-15-26-13-7-4-8-14-26/h5-6,9-12H,3-4,7-8,13-17H2,1-2H3

Standard InChI Key:  NTKKYYXVVRAMIR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    5.1343   -3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2228   -4.2238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8965   -3.0595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4197   -2.9889    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0358   -4.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4482   -3.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6947   -3.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9748   -2.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9820   -2.1604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6086   -4.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1665   -6.1488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2608   -3.4084    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4138   -2.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -1.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7807   -5.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2693   -0.9190    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5430   -2.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388   -2.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4658   -5.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6956   -1.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2834   -3.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3822   -5.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3443   -6.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5494   -0.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2937   -5.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7660   -6.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7357   -7.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5456    0.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7025   -4.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9438   -7.2621    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 15  1  0
 12  8  2  0
 13  4  1  0
 14  9  2  0
 15 10  1  0
 16 14  1  0
 17 12  1  0
 18 17  2  0
 19  5  2  0
 20  9  1  0
 21  6  2  0
 22 11  1  0
 23 11  1  0
 24 16  1  0
 25 19  1  0
 26 22  1  0
 27 23  1  0
 28 24  1  0
 29 21  1  0
 30 27  1  0
  5  6  1  0
 25 29  2  0
 14 18  1  0
 30 26  1  0
M  CHG  2   4   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA9842

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

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: 442.65

Molecular Weight (Monoisotopic): 442.1861

AlogP: 4.65

#Rotatable Bonds: 8

Polar Surface Area: 57.01

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.04

CX Basic pKa: 7.75

CX LogP: 4.21

CX LogD: 3.70

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -1.24

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