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

ID: ALA135755

PubChem CID: 10916047

Max Phase: Preclinical

Molecular Formula: C22H26O6

Molecular Weight: 386.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC(=O)OCOC(=O)CCCCCC1=C(C)C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C22H26O6/c1-3-9-19(23)27-14-28-20(24)13-6-4-5-10-16-15(2)21(25)17-11-7-8-12-18(17)22(16)26/h7-8,11-12H,3-6,9-10,13-14H2,1-2H3

Standard InChI Key:  MOVODEWFRQNJME-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    1.5042   -1.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -2.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0792   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6500   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7792   -3.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000   -0.1167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167   -2.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292   -2.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -2.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -1.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6542   -1.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2167   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2250   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3625   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375   -2.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0792   -2.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3375   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7917   -2.6542    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 21  1  0
  8 12  1  0
  9  4  2  0
 10  3  2  0
 11 13  1  0
 12 11  1  0
 13  7  1  0
 14  7  2  0
 15  8  2  0
 16  2  1  0
 17  1  1  0
 18  5  1  0
 19  6  1  0
 20  8  1  0
 21 24  1  0
 22 16  1  0
 23 20  1  0
 24 25  1  0
 25 22  1  0
 26 27  1  0
 27 18  2  0
 28 23  1  0
  4  6  1  0
 26 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA135755

   Butanoyloxymethyl 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: 386.44

Molecular Weight (Monoisotopic): 386.1729

AlogP: 4.18

#Rotatable Bonds: 10

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: 4.34

CX LogD: 4.34

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.34

Np Likeness Score: 0.83

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