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

ID: ALA135287

Max Phase: Preclinical

Molecular Formula: C17H18O4

Molecular Weight: 286.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H18O4/c1-11-12(7-3-2-4-10-15(18)19)17(21)14-9-6-5-8-13(14)16(11)20/h5-6,8-9H,2-4,7,10H2,1H3,(H,18,19)

Standard InChI Key:  ICGRXHWXPCXIKM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.0803   -2.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658   -1.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658   -0.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0803   -0.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7947   -0.8124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7947   -1.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0631   -0.8124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513   -0.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0803    0.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658    0.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6513    0.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7947    0.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658    1.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0631    0.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776    0.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4921    0.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2066    0.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9210    0.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355    0.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500    0.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -0.3999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  2  0
  2  3  2  0
  3  4  1  0
  8  3  1  0
  4  5  2  0
  9  4  1  0
  5  6  1  0
  8  7  2  0
  8 11  1  0
  9 10  1  0
  9 12  2  0
 10 11  2  0
 10 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA135287

   ---

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: 286.33

Molecular Weight (Monoisotopic): 286.1205

AlogP: 3.42

#Rotatable Bonds: 6

Polar Surface Area: 71.44

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.99

CX Basic pKa: ┄

CX LogP: 3.19

CX LogD: 0.02

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.81

Np Likeness Score: 1.03

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]

2. Salmon-Chemin L, Buisine E, Yardley V, Kohler S, Debreu MA, Landry V, Sergheraert C, Croft SL, Krauth-Siegel RL, Davioud-Charvet E..  (2001)  2- and 3-substituted 1,4-naphthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from Trypanosoma cruzi: synthesis and correlation between redox cycling activities and in vitro cytotoxicity.,  44  (4): [PMID:11170645] [10.1021/jm001079l]

3. Biot C, Bauer H, Schirmer RH, Davioud-Charvet E..  (2004)  5-substituted tetrazoles as bioisosteres of carboxylic acids. Bioisosterism and mechanistic studies on glutathione reductase inhibitors as antimalarials.,  47  (24): [PMID:15537352] [10.1021/jm0497545]

4. Woolley KL, Nadikudi M, Koupaei MN, Corban M, McCartney P, Bissember AC, Lewis TW, Gueven N, Smith JA..  (2019)  Amide linked redox-active naphthoquinones for the treatment of mitochondrial dysfunction.,  10  (3): [PMID:30996858] [10.1039/C8MD00582F]

Source

Source(1):

• Scientific Literature