2,3-Dichloro-5,8-dimethoxy-[1,4]naphthoquinone

ID: ALA131037

PubChem CID: 375895

Max Phase: Preclinical

Molecular Formula: C12H8Cl2O4

Molecular Weight: 287.10

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c2c1C(=O)C(Cl)=C(Cl)C2=O

Standard InChI:  InChI=1S/C12H8Cl2O4/c1-17-5-3-4-6(18-2)8-7(5)11(15)9(13)10(14)12(8)16/h3-4H,1-2H3

Standard InChI Key:  DRGCWMGLVXZPIZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    2.4875   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4875   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -0.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667    0.4333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7625   -2.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -0.4042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2000   -2.0625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833   -0.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    0.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292   -2.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3833    0.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  4  2  0
  4  5  1  0
  5  1  1  0
  6  2  1  0
  7  4  1  0
  8  3  1  0
  9  6  2  0
 10  5  2  0
 11  2  1  0
 12  1  1  0
 13 14  1  0
 14  7  2  0
 15  8  1  0
 16  7  1  0
 17 16  1  0
 18 15  1  0
  3  6  1  0
  8 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA131037

   2,3-Dichloro-5,8-dimethoxy-1,4-naphthoquinone

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: 287.10

Molecular Weight (Monoisotopic): 285.9800

AlogP: 2.77

#Rotatable Bonds: 2

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.96

CX LogD: 1.96

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.84

Np Likeness Score: 0.36

References

1. Chang HX, Chou TC, Savaraj N, Liu LF, Yu C, Cheng CC..  (1999)  Design of antineoplastic agents based on the "2-phenylnaphthalene-type" structural pattern. 4. Synthesis and biological activity of 2-chloro-3-(substituted phenoxy)-1, 4-naphthoquinones and related 5,8-dihydroxy-1,4-naphthoquinones.,  42  (3): [PMID:9986711] [10.1021/jm9804679]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. Badolato M, Carullo G, Caroleo MC, Cione E, Aiello F, Manetti F..  (2019)  Discovery of 1,4-Naphthoquinones as a New Class of Antiproliferative Agents Targeting GPR55.,  10  (4): [PMID:30996770] [10.1021/acsmedchemlett.8b00333]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays