3-ethoxy-6-(2-(1-(6-methylpyridazin-3-yl)piperidin-4-yl)ethoxy)benzo[d]isothiazole

ID: ALA2062893

PubChem CID: 504462

Max Phase: Preclinical

Molecular Formula: C21H26N4O2S

Molecular Weight: 398.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1nsc2cc(OCCC3CCN(c4ccc(C)nn4)CC3)ccc12

Standard InChI:  InChI=1S/C21H26N4O2S/c1-3-26-21-18-6-5-17(14-19(18)28-24-21)27-13-10-16-8-11-25(12-9-16)20-7-4-15(2)22-23-20/h4-7,14,16H,3,8-13H2,1-2H3

Standard InChI Key:  WKGISLZZMYJORN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   16.1383   -5.2762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5511   -4.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1378   -3.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3114   -3.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9063   -4.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0813   -4.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3762   -4.5646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7847   -5.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6061   -5.2842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0247   -4.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6116   -3.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7839   -3.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8498   -4.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2631   -3.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0881   -3.8642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4998   -4.5809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0821   -5.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4932   -6.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3230   -4.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7323   -5.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3194   -6.0090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8693   -6.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6262   -6.2882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5414   -5.4652    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.6972   -7.4287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9120   -7.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7399   -8.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
 11 14  1  0
  6  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  1  0
  3  8  1  0
 16 17  1  0
  8  9  1  0
 17 18  2  0
 18 19  1  0
 19 22  2  0
  4  5  1  0
 21 20  2  0
 20 17  1  0
 21 22  1  0
  2  3  1  0
  5  6  2  0
  6  1  1  0
  8 13  1  0
  9 10  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
 10 11  1  0
 23 26  1  0
 11 12  1  0
 26 27  1  0
 12 13  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2062893

   3-Ethoxy-6-{2-[1-(6-methylpyridazin-3-yl)piperidin-4-yl]ethoxy}-1,2-benzisothiazole

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: 398.53

Molecular Weight (Monoisotopic): 398.1776

AlogP: 4.48

#Rotatable Bonds: 7

Polar Surface Area: 60.37

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.41

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.78

References

1. Feil SC, Hamilton S, Krippner GY, Lin B, Luttick A, McConnell DB, Nearn R, Parker MW, Ryan J, Stanislawski PC, Tucker SP, Watson KG, Morton CJ..  (2012)  An Orally Available 3-Ethoxybenzisoxazole Capsid Binder with Clinical Activity against Human Rhinovirus.,  3  (4): [PMID:24900468] [10.1021/ml2002955]

Source

Source(1):

• Scientific Literature