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

ID: ALA152868

Max Phase: Preclinical

Molecular Formula: C14H12O4

Molecular Weight: 244.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H12O4/c1-8-9(6-7-12(15)16)14(18)11-5-3-2-4-10(11)13(8)17/h2-5H,6-7H2,1H3,(H,15,16)

Standard InChI Key:  XDYLYDATVANZFF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    2.6667   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6667   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6250   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6250   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292    0.6333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -1.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -2.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2125   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -1.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5875   -0.8542    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  6  2  0
  6  3  1  0
  7  1  1  0
  8 12  1  0
  9  4  2  0
 10  3  2  0
 11  8  2  0
 12  7  1  0
 13  2  1  0
 14  8  1  0
 15  6  1  0
 16  5  1  0
 17 18  1  0
 18 15  2  0
  5  4  1  0
 16 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA152868

   ---

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: 244.25

Molecular Weight (Monoisotopic): 244.0736

AlogP: 2.25

#Rotatable Bonds: 3

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: 3.83

CX Basic pKa: ┄

CX LogP: 1.85

CX LogD: -1.40

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.88

Np Likeness Score: 0.96

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. 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]

3. Gong Q, Yang F, Hu J, Li T, Wang P, Li X, Zhang X..  (2021)  Rational designed highly sensitive NQO1-activated near-infrared fluorescent probe combined with NQO1 substrates in vivo: An innovative strategy for NQO1-overexpressing cancer theranostics.,  224  [PMID:34303080] [10.1016/j.ejmech.2021.113707]

Source

Source(1):

• Scientific Literature