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

ID: ALA133305

PubChem CID: 10979501

Max Phase: Preclinical

Molecular Formula: C18H20O4

Molecular Weight: 300.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CCCCCC1=C(C)C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C18H20O4/c1-12-13(8-4-3-5-11-16(19)22-2)18(21)15-10-7-6-9-14(15)17(12)20/h6-7,9-10H,3-5,8,11H2,1-2H3

Standard InChI Key:  AHJBLLMXMBGUNZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    0.9375   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375   -4.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167   -5.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4875   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125   -6.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -2.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250   -4.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -4.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6417   -5.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -5.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -5.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6500   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -4.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7875   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125   -3.9917    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  4  2  0
  8  3  2  0
  9 16  1  0
 10  9  2  0
 11  2  1  0
 12  1  1  0
 13  9  1  0
 14  6  1  0
 15  5  1  0
 16 19  1  0
 17 13  1  0
 18 11  1  0
 19 20  1  0
 20 18  1  0
 21 22  1  0
 22 15  2  0
  4  6  1  0
 21 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA133305

   Methyl 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: 300.35

Molecular Weight (Monoisotopic): 300.1362

AlogP: 3.51

#Rotatable Bonds: 6

Polar Surface Area: 60.44

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.33

CX LogD: 3.33

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.60

Np Likeness Score: 0.89

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