N-[2-(1-Pyridin-2-yl-1,4,5,6-tetrahydro-cyclopentaimidazole-2-sulfinylmethyl)-phenyl]-acetamide

ID: ALA435446

PubChem CID: 10762332

Max Phase: Preclinical

Molecular Formula: C20H20N4O2S

Molecular Weight: 380.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1ccccc1C[S+]([O-])c1nc2c(n1-c1ccccn1)CCC2

Standard InChI:  InChI=1S/C20H20N4O2S/c1-14(25)22-16-8-3-2-7-15(16)13-27(26)20-23-17-9-6-10-18(17)24(20)19-11-4-5-12-21-19/h2-5,7-8,11-12H,6,9-10,13H2,1H3,(H,22,25)

Standard InChI Key:  QXQYLRXBVGEHIL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    5.1233   -3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8643   -3.0510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2195   -4.2052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4803   -3.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4157   -2.9891    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.0185   -4.3702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9837   -2.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7142   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7148   -4.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3057   -4.2129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0088   -4.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5997   -4.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3511   -1.7342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4094   -2.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6036   -5.4329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3607   -3.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6123   -5.0487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4246   -4.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7424   -1.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4421   -4.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0127   -5.4348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4704   -0.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899   -4.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4353   -5.4308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8548   -1.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2212   -0.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7294   -5.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  1  0
  5  1  1  0
  6  3  1  0
  7  2  1  0
  8  5  1  0
  9  8  1  0
 10 11  1  0
 11  9  1  0
 12 10  1  0
 13  7  2  0
 14  5  1  0
 15 12  2  0
 16  4  1  0
 17  6  1  0
 18  9  2  0
 19  7  1  0
 20 17  1  0
 21 11  2  0
 22 13  1  0
 23 12  1  0
 24 18  1  0
 25 19  2  0
 26 25  1  0
 27 24  2  0
  4  6  2  0
 20 16  1  0
 26 22  2  0
 27 21  1  0
M  CHG  2   5   1  14  -1
M  END

Alternative Forms

1. Parent:

   

   ALA435446

   N-[2-[(3-pyridin-2-yl-5,6-dihydro-4H-cyclopenta[d]imidazol-2-yl)sulfinylmethyl]phenyl]acetamide

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: 380.47

Molecular Weight (Monoisotopic): 380.1307

AlogP: 3.02

#Rotatable Bonds: 5

Polar Surface Area: 82.87

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.97

CX Basic pKa: 2.04

CX LogP: 2.29

CX LogD: 2.29

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -1.44

References

1. Yamada M, Yura T, Morimoto M, Harada T, Yamada K, Honma Y, Kinoshita M, Sugiura M..  (1996)  2-[(2-Aminobenzyl)sulfinyl]-1-(2-pyridyl)-1,4,5,6-tetrahydrocyclopent[d]imidazoles as a novel class of gastric H+/K+-ATPase inhibitors.,  39  (2): [PMID:8558532] [10.1021/jm950610n]

Source

Source(1):

• Scientific Literature