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

ID: ALA152263

Max Phase: Preclinical

Molecular Formula: C14H12O5

Molecular Weight: 260.24

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H12O5/c1-7-8(5-6-11(16)17)14(19)12-9(13(7)18)3-2-4-10(12)15/h2-4,15H,5-6H2,1H3,(H,16,17)

Standard InChI Key:  NXZAUINGPRFZPU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    4.8292   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3125   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3125   -2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8875   -3.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250   -3.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000   -3.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8250   -1.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -4.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000   -3.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8000   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9292   -3.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -3.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750   -2.7167    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  2  1  0
  8  1  2  0
  9  3  1  0
 10 13  1  0
 11  5  2  0
 12 10  2  0
 13  7  1  0
 14  6  1  0
 15  4  1  0
 16 10  1  0
 17  9  1  0
 18 19  1  0
 19  9  2  0
  4  5  1  0
 18 14  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA152263

   ---

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: 260.24

Molecular Weight (Monoisotopic): 260.0685

AlogP: 1.95

#Rotatable Bonds: 3

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: 2.20

CX LogD: -1.19

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.87

Np Likeness Score: 1.49

References

1. 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]

2. Bao N, Ou J, Xu M, Guan F, Shi W, Sun J, Chen L..  (2017)  Novel NO-releasing plumbagin derivatives: Design, synthesis and evaluation of antiproliferative activity.,  137  [PMID:28558333] [10.1016/j.ejmech.2017.05.046]

3. Bao N, Ou J, Li N, Zou P, Sun J, Chen L..  (2018)  Novel anticancer hybrids from diazen-1-ium-1,2-diolate nitric oxide donor and ROS inducer plumbagin: Design, synthesis and biological evaluations.,  154  [PMID:29772386] [10.1016/j.ejmech.2018.04.047]

Source

Source(1):

• Scientific Literature