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

ID: ALA2062774

Cas Number: 439085-51-5

PubChem CID: 504457

Product Number: V670985, Order Now?

Max Phase: Phase

Molecular Formula: C21H26N4O3

Molecular Weight: 382.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bta798 | Vapendavir | BTA-798 | BTA798 | Vapendavir|439085-51-5|BTA798|Vapendavir [INN]|3-Ethoxy-6-(2-(1-(6-methylpyridazin-3-yl)piperidin-4-yl)ethoxy)benzo[d]isoxazole|Q8LVL5Z68H|BTA-798|1,2-Benzisoxazole, 3-ethoxy-6-[2-[1-(6-methyl-3-pyridazinyl)-4-piperidinyl]ethoxy]-|3-Ethoxy-6-(2-(1-(6-methylpyridazin-3-yl)piperidin-4-yl)ethoxy)-1,2-benzoxazole|3-ethoxy-6-[2-[1-(6-methylpyridazin-3-yl)piperidin-4-yl]ethoxy]-1,2-benzoxazole|3-Ethoxy-6-{2-[1-(6-Methylpyridazin-3-Yl)piperidin-4-Yl]ethoxy}-1,2-Show More⌵

Canonical SMILES:  CCOc1noc2cc(OCCC3CCN(c4ccc(C)nn4)CC3)ccc12

Standard InChI:  InChI=1S/C21H26N4O3/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:  DKSVBVKHUICELN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   -4.2372    0.3469    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4139    0.3457    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011    1.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4144    1.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2408    1.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6459    1.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4708    1.0532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1760    1.0573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7675    0.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9461    0.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5275    1.0508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9406    1.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7683    1.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2976    1.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7109    1.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    1.7577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9477    1.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5299    0.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9410   -0.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7708    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1801    0.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7673   -0.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3171   -1.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0740   -0.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9892    0.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451   -1.8069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3598   -2.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878   -2.8701    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:

   

   ALA2062774

   Vapendavir

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 382.46

Molecular Weight (Monoisotopic): 382.2005

AlogP: 4.01

#Rotatable Bonds: 7

Polar Surface Area: 73.51

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.41

CX LogP: 3.27

CX LogD: 3.27

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.61

Np Likeness Score: -1.57

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]

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

3. Kim J, Jung YK, Kim C, Shin JS, Scheers E, Lee JY, Han SB, Lee CK, Neyts J, Ha JD, Jung YS..  (2017)  A Novel Series of Highly Potent Small Molecule Inhibitors of Rhinovirus Replication.,  60  (13): [PMID:28581749] [10.1021/acs.jmedchem.7b00175]

4. Unpublished dataset, 

5. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

6. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(5):

• Scientific Literature
• Clinical Candidates
• AstraZeneca Deposited Data
• CO-ADD antimicrobial screening data
• IMI-CARE SARS-CoV-2 Data