10'b-[(2Z)-4-hydroxybut-2-en-2-yl]-4'a,5',6',10'b-tetrahydrospiro[adamantane-2,3'-naphtho[2,1-e][1,2,4]trioxin]-6'-one

ID: ALA5198523

PubChem CID: 168289780

Max Phase: Preclinical

Molecular Formula: C24H28O5

Molecular Weight: 396.48

Names and Identifiers

Canonical SMILES:  C/C(=C/CO)C12OOC3(OC1CC(=O)c1ccccc12)C1CC2CC(C1)CC3C2

Standard InChI:  InChI=1S/C24H28O5/c1-14(6-7-25)23-20-5-3-2-4-19(20)21(26)13-22(23)27-24(29-28-23)17-9-15-8-16(11-17)12-18(24)10-15/h2-6,15-18,22,25H,7-13H2,1H3/b14-6-

Standard InChI Key:  CTJJZTAUPBZKSL-NSIKDUERSA-N

Molfile:  

 
     RDKit          2D

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   40.9650  -18.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2571  -19.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7134  -18.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0564  -19.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3605  -18.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9982  -18.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3216  -17.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7205  -18.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1186  -17.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0650  -17.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6399  -18.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0317  -18.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8776  -17.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2718  -18.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8477  -18.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2407  -19.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0593  -19.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8181  -20.2115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   39.4800  -18.8317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2939  -18.8524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.3314  -17.4366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5114  -17.4142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8719  -17.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4482  -16.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1641  -16.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2630  -16.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6704  -16.0341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5198523

   ---

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: 396.48

Molecular Weight (Monoisotopic): 396.1937

AlogP: 3.91

#Rotatable Bonds: 2

Polar Surface Area: 64.99

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: 3.88

CX LogD: 3.88

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.61

Np Likeness Score: 1.44

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