5-(8-Hydroxy-3-methyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-pentanoic acid

ID: ALA135504

Max Phase: Preclinical

Molecular Formula: C16H16O5

Molecular Weight: 288.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(CCCCC(=O)O)C(=O)c2c(O)cccc2C1=O

Standard InChI:  InChI=1S/C16H16O5/c1-9-10(5-2-3-8-13(18)19)16(21)14-11(15(9)20)6-4-7-12(14)17/h4,6-7,17H,2-3,5,8H2,1H3,(H,18,19)

Standard InChI Key:  QMRPDNQZHUUULQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    3.6542   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417   -4.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -0.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9375   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9292   -4.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2292   -1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -1.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6542   -3.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -4.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2250   -3.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -2.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8000   -2.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -3.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  2  0
  5  6  1  0
  6  3  2  0
  7  1  2  0
  8  3  1  0
  9  5  2  0
 10 18  1  0
 11 10  2  0
 12  6  1  0
 13  2  1  0
 14  4  1  0
 15 10  1  0
 16  8  1  0
 17 19  1  0
 18 21  1  0
 19  8  2  0
 20 13  1  0
 21 20  1  0
  5  4  1  0
 17 12  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA135504

   ---

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: 288.30

Molecular Weight (Monoisotopic): 288.0998

AlogP: 2.73

#Rotatable Bonds: 5

Polar Surface Area: 91.67

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.61

CX Basic pKa: ┄

CX LogP: 3.09

CX LogD: -0.31

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.81

Np Likeness Score: 1.51

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]

Source

Source(1):

• Scientific Literature