2-(4-(1-(1,2,5-trioxaspiro[5.5]undecan-3-yl)vinyl)naphthalen-1-yloxy)ethanol

ID: ALA5202990

PubChem CID: 168292891

Max Phase: Preclinical

Molecular Formula: C22H26O5

Molecular Weight: 370.45

Names and Identifiers

Canonical SMILES:  C=C(c1ccc(OCCO)c2ccccc12)C1COC2(CCCCC2)OO1

Standard InChI:  InChI=1S/C22H26O5/c1-16(21-15-25-22(27-26-21)11-5-2-6-12-22)17-9-10-20(24-14-13-23)19-8-4-3-7-18(17)19/h3-4,7-10,21,23H,1-2,5-6,11-15H2

Standard InChI Key:  DJKQMEYVBDTUGF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   19.6745   -4.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6704   -5.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3721   -6.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0825   -5.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0866   -4.8030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3804   -4.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7328   -2.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7316   -3.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1465   -2.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4379   -2.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1494   -3.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4362   -3.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4317   -4.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1387   -5.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8519   -4.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8580   -3.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7212   -5.1737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0164   -4.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3059   -5.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6010   -4.7506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5674   -3.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2734   -3.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5707   -2.7340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2657   -4.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9677   -5.1961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6847   -3.9758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9783   -3.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  2  0
  8 12  1  0
 11  9  1  0
  9 10  2  0
 10  7  1  0
 11 12  2  0
 11 16  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 22 27  1  0
 24 25  1  0
 25  1  1  0
  1 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5202990

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 370.45

Molecular Weight (Monoisotopic): 370.1780

AlogP: 4.23

#Rotatable Bonds: 5

Polar Surface Area: 57.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.38

CX LogD: 4.38

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.80

Np Likeness Score: 0.56

References

1. Karnatak M, Hassam M, Vanangamudi M, Sharma S, Kumar Yadav D, Singh C, Puri SK, Rawat V, Prakash Verma V..  (2021)  Novel naphthyl based 1,2,4-trioxanes: Synthesis and in vivo efficacy in the Plasmodium yoelii nigeriensis in Swiss mice.,  51  [PMID:34547418] [10.1016/j.bmcl.2021.128372]

Source

Source(1):

• Scientific Literature