5-(3-Methyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-pentanoic acid

ID: ALA134615

Max Phase: Preclinical

Molecular Formula: C16H16O4

Molecular Weight: 272.30

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H16O4/c1-10-11(6-4-5-9-14(17)18)16(20)13-8-3-2-7-12(13)15(10)19/h2-3,7-8H,4-6,9H2,1H3,(H,17,18)

Standard InChI Key:  JXMRBOOZUWPZPG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    4.0625   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6292   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -2.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542    0.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6292   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6250   -2.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -1.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3417   -1.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9167   -1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917   -1.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2000   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -1.3542    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  5  1  0
 15  6  1  0
 16 18  1  0
 17 11  1  0
 18 17  1  0
 19 14  2  0
 20 19  1  0
  6  4  1  0
 15 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA134615

   ---

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: 272.30

Molecular Weight (Monoisotopic): 272.1049

AlogP: 3.03

#Rotatable Bonds: 5

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: 3.86

CX Basic pKa: ┄

CX LogP: 2.74

CX LogD: -0.49

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.84

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