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

ID: ALA5206511

PubChem CID: 168295651

Max Phase: Preclinical

Molecular Formula: C20H24O5

Molecular Weight: 344.41

Names and Identifiers

Canonical SMILES:  C/C(=C/CO)C12OOC3(CCCCC3)OC1CC(=O)c1ccccc12

Standard InChI:  InChI=1S/C20H24O5/c1-14(9-12-21)20-16-8-4-3-7-15(16)17(22)13-18(20)23-19(24-25-20)10-5-2-6-11-19/h3-4,7-9,18,21H,2,5-6,10-13H2,1H3/b14-9-

Standard InChI Key:  HYTYVXOSYHLJQN-ZROIWOOFSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   22.2705  -18.1970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6750  -18.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4839  -18.9053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8945  -18.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4901  -17.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6750  -17.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6053  -17.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1789  -18.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5718  -18.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4202  -17.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8155  -18.1412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3903  -18.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7844  -19.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6053  -19.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3605  -20.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6349  -18.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0272  -18.8751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8433  -18.8958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8810  -17.4760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0587  -17.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4174  -17.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9952  -16.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7075  -16.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8124  -16.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2210  -16.0695    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  9  1  0
  9 12  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 17  1  0
 13 15  2  0
 16 17  1  0
 16 20  1  0
 17 18  1  0
 18  1  1  0
  1 19  1  0
 19 20  1  0
 16 21  1  0
 21 22  2  0
 21 23  1  0
 22 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5206511

   ---

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: 344.41

Molecular Weight (Monoisotopic): 344.1624

AlogP: 3.41

#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: 3.28

CX LogD: 3.28

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.66

Np Likeness Score: 1.35

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