6-(2-(1-(6-methylpyridazin-3-yl)piperidin-4-yl)ethoxy)-3-propylbenzo[d]isoxazole

ID: ALA2062892

PubChem CID: 504461

Max Phase: Preclinical

Molecular Formula: C22H28N4O2

Molecular Weight: 380.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1noc2cc(OCCC3CCN(c4ccc(C)nn4)CC3)ccc12

Standard InChI:  InChI=1S/C22H28N4O2/c1-3-4-20-19-7-6-18(15-21(19)28-25-20)27-14-11-17-9-12-26(13-10-17)22-8-5-16(2)23-24-22/h5-8,15,17H,3-4,9-14H2,1-2H3

Standard InChI Key:  PRBJCWJHTRNWKM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.1695   -5.0839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9927   -5.0850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4055   -4.3732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9922   -3.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1659   -3.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7608   -4.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9358   -4.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2305   -4.3734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6389   -5.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4603   -5.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8789   -4.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4657   -3.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6382   -3.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7039   -4.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1170   -3.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9420   -3.6732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3537   -4.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9361   -5.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3471   -5.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1769   -4.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5861   -5.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1733   -5.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7231   -6.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4799   -6.0970    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3951   -5.2740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5510   -7.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7658   -7.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5937   -8.3005    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:

   

   ALA2062892

   6-[2-[1-(6-Methylpyridazin-3-yl)-4-piperidyl]ethoxy]-3-propyl-1,2-benzoxazole

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: 380.49

Molecular Weight (Monoisotopic): 380.2212

AlogP: 4.56

#Rotatable Bonds: 7

Polar Surface Area: 64.28

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.41

CX LogP: 3.75

CX LogD: 3.75

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: -1.58

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