2-(4-(1-(6,7,10-trioxaspiro[4.5]decan-8-yl)vinyl)naphthalen-1-yloxy)-2-methylpropan-1-ol

ID: ALA5200738

PubChem CID: 168290798

Max Phase: Preclinical

Molecular Formula: C23H28O5

Molecular Weight: 384.47

Names and Identifiers

Canonical SMILES:  C=C(c1ccc(OC(C)(C)CO)c2ccccc12)C1COC2(CCCC2)OO1

Standard InChI:  InChI=1S/C23H28O5/c1-16(21-14-25-23(28-27-21)12-6-7-13-23)17-10-11-20(26-22(2,3)15-24)19-9-5-4-8-18(17)19/h4-5,8-11,21,24H,1,6-7,12-15H2,2-3H3

Standard InChI Key:  MXBPBYALVPAEPQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    3.9250  -11.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3377  -12.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7461  -11.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0002  -12.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9961  -13.0177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7720  -13.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2558  -12.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7787  -11.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0544  -10.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0533  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4682  -10.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7595   -9.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4710  -10.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7579  -11.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7534  -12.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4604  -12.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1735  -12.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1797  -11.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0429  -12.5780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6275  -12.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9226  -12.1549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8890  -10.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5951  -11.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8924  -10.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5874  -12.1890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2893  -12.6003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0064  -11.3800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2999  -10.9641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  9 10  2  0
 10 14  1  0
 13 11  1  0
 11 12  2  0
 12  9  1  0
 13 14  2  0
 13 18  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 15 19  1  0
 19  2  1  0
  2 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 23 28  1  0
 25 26  1  0
 26  4  1  0
  4 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5200738

   ---

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: 384.47

Molecular Weight (Monoisotopic): 384.1937

AlogP: 4.62

#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: 4.63

CX LogD: 4.63

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.76

Np Likeness Score: 0.62

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