4-(2-(7-(4-(1-(1,2,5-trioxaspiro[5.5]undecan-3-yl)vinyl)phenoxy)naphthalen-2-yloxy)ethoxy)-4-oxobutanoic acid

ID: ALA4847036

PubChem CID: 44236223

Max Phase: Preclinical

Molecular Formula: C32H34O9

Molecular Weight: 562.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C(c1ccc(Oc2ccc3ccc(OCCOC(=O)CCC(=O)O)cc3c2)cc1)C1COC2(CCCCC2)OO1

Standard InChI:  InChI=1S/C32H34O9/c1-22(29-21-38-32(41-40-29)15-3-2-4-16-32)23-5-9-26(10-6-23)39-28-12-8-24-7-11-27(19-25(24)20-28)36-17-18-37-31(35)14-13-30(33)34/h5-12,19-20,29H,1-4,13-18,21H2,(H,33,34)

Standard InChI Key:  ZDEZXXOKXRSANV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 41 45  0  0  0  0  0  0  0  0999 V2000
   13.1741  -23.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8799  -23.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5827  -23.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5859  -22.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8802  -22.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1712  -22.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6912  -23.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6901  -24.3117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981  -24.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3964  -23.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1050  -23.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1057  -24.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8143  -24.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5225  -24.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5178  -23.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8087  -23.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834  -23.0837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2230  -23.0688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9332  -23.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9335  -24.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6429  -24.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3491  -24.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3414  -23.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6315  -23.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0598  -24.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0659  -25.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7645  -24.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4717  -24.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1742  -24.2662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4618  -23.0431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7531  -23.4551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758  -23.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5680  -23.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8604  -23.4928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1474  -23.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4431  -23.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1406  -24.7138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4498  -22.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609  -22.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8652  -22.6768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1677  -21.4452    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
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  7 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 22 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 31  1  0
 28 29  1  0
 29  1  1  0
  1 30  1  0
 30 31  1  0
 17 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 36 38  1  0
 38 39  1  0
 39 40  1  0
 39 41  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4847036

   4-Oxo-4-[2-[7-[4-[1-(1,2,5-trioxaspiro[5.5]undecan-3-yl)ethenyl]phenoxy]naphthalen-2-yl]oxyethoxy]butanoic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 562.62

Molecular Weight (Monoisotopic): 562.2203

AlogP: 6.44

#Rotatable Bonds: 11

Polar Surface Area: 109.75

Molecular Species: ACID

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.67

CX Basic pKa: ┄

CX LogP: 6.15

CX LogD: 2.83

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.16

Np Likeness Score: 0.23

References

1. Shukla M, Hassam M, Kumar Yadav D, Sharma S, Singh C, Puri SK, Shrivastava R, Prakash Verma V..  (2021)  Synthesis of novel 1,2,4-trioxanes and antimalarial evaluation against multidrug-resistant Plasmodium yoelii nigeriensis.,  49  [PMID:34365007] [10.1016/j.bmcl.2021.128305]

Source

Source(1):

• Scientific Literature