(Z)-10b-(4-hydroxybut-2-en-2-yl)-3,3-dimethyl-4a,5-dihydronaphtho[2,1-e][1,2,4]trioxin-6(10bH)-one

ID: ALA5196101

PubChem CID: 168287663

Max Phase: Preclinical

Molecular Formula: C17H20O5

Molecular Weight: 304.34

Names and Identifiers

Canonical SMILES:  C/C(=C/CO)C12OOC(C)(C)OC1CC(=O)c1ccccc12

Standard InChI:  InChI=1S/C17H20O5/c1-11(8-9-18)17-13-7-5-4-6-12(13)14(19)10-15(17)20-16(2,3)21-22-17/h4-8,15,18H,9-10H2,1-3H3/b11-8-

Standard InChI Key:  WRHXICCDQQMINE-FLIBITNWSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   31.9613  -17.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2555  -18.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9658  -18.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5903  -17.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1639  -18.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5568  -18.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4052  -17.3568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8005  -18.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3753  -18.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7694  -19.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5902  -19.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3455  -20.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6198  -18.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0121  -18.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8283  -18.8256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8660  -17.4059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0437  -17.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4024  -17.2890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9802  -16.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6925  -16.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7974  -16.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2060  -15.9993    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  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 14  1  0
 10 12  2  0
 13 14  1  0
 13 17  1  0
 14 15  1  0
 15  2  1  0
  2 16  1  0
 16 17  1  0
 13 18  1  0
 18 19  2  0
 18 20  1  0
 19 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5196101

   ---

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: 304.34

Molecular Weight (Monoisotopic): 304.1311

AlogP: 2.49

#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: 2.02

CX LogD: 2.02

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.67

Np Likeness Score: 1.49

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