6-(3-Methyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-hexanoic acid 2,2-dimethyl-propionyloxymethyl ester

ID: ALA133306

PubChem CID: 10927492

Max Phase: Preclinical

Molecular Formula: C23H28O6

Molecular Weight: 400.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(CCCCCC(=O)OCOC(=O)C(C)(C)C)C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C23H28O6/c1-15-16(21(26)18-12-9-8-11-17(18)20(15)25)10-6-5-7-13-19(24)28-14-29-22(27)23(2,3)4/h8-9,11-12H,5-7,10,13-14H2,1-4H3

Standard InChI Key:  AOBNIFUJMJOAQV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
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   -0.7583   -2.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1875   -2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4708    0.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833   -3.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -2.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -2.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875   -1.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -1.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0500   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8958   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8958   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0917   -3.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8125   -2.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3792   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6083   -2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6083   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  5  2  0
  7 12  1  0
  8  7  1  0
  9 21  1  0
 10  3  2  0
 11  4  2  0
 12 13  1  0
 13 14  1  0
 14  9  1  0
 15  7  2  0
 16  9  2  0
 17  2  1  0
 18  1  1  0
 19  6  1  0
 20  5  1  0
 21 26  1  0
 22  8  1  0
 23  8  1  0
 24  8  1  0
 25 17  1  0
 26 27  1  0
 27 25  1  0
 28 29  1  0
 29 20  2  0
  4  6  1  0
 19 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA133306

   2,2-Dimethylpropanoyloxymethyl 6-(3-methyl-1,4-dioxonaphthalen-2-yl)hexanoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 400.47

Molecular Weight (Monoisotopic): 400.1886

AlogP: 4.42

#Rotatable Bonds: 8

Polar Surface Area: 86.74

Molecular Species: ┄

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.99

CX LogD: 4.99

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.36

Np Likeness Score: 0.77

References

1. Davioud-Charvet E, Delarue S, Biot C, Schwöbel B, Boehme CC, Müssigbrodt A, Maes L, Sergheraert C, Grellier P, Schirmer RH, Becker K..  (2001)  A prodrug form of a Plasmodium falciparum glutathione reductase inhibitor conjugated with a 4-anilinoquinoline.,  44  (24): [PMID:11708927] [10.1021/jm010268g]

Source

Source(1):

• Scientific Literature