2-Chloro-3-((3-hydroxyphenyl)amino)naphthalene-1,4-dione

ID: ALA4778983

PubChem CID: 4247627

Max Phase: Preclinical

Molecular Formula: C16H10ClNO3

Molecular Weight: 299.71

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(Cl)=C(Nc2cccc(O)c2)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C16H10ClNO3/c17-13-14(18-9-4-3-5-10(19)8-9)16(21)12-7-2-1-6-11(12)15(13)20/h1-8,18-19H

Standard InChI Key:  XCMJGNUGOYSYEP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   11.8975  -10.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6066  -10.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6066   -9.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8975   -9.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1926   -9.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4835   -9.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7744   -9.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7744  -10.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4835  -10.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1926  -10.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8975  -11.6976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8975   -8.4288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3157   -9.2460    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0207   -9.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0207  -10.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7298  -10.8804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4388  -10.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4388   -9.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7298   -9.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3157  -10.8804    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.1531   -9.2418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  1  0
  5 10  2  0
  1 11  2  0
  4 12  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 13 14  1  0
  3 13  1  0
  2 20  1  0
 18 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4778983

   2-Chloro-3-(3-hydroxy-phenylamino)-[1,4]naphthoquinone

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 299.71

Molecular Weight (Monoisotopic): 299.0349

AlogP: 3.33

#Rotatable Bonds: 2

Polar Surface Area: 66.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.28

CX Basic pKa: ┄

CX LogP: 2.50

CX LogD: 2.49

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.89

Np Likeness Score: -0.20

References

1. Varricchio C,Beirne K,Aeschlimann P,Heard C,Rozanowska M,Votruba M,Brancale A.  (2020)  Discovery of Novel 2-Aniline-1,4-naphthoquinones as Potential New Drug Treatment for Leber's Hereditary Optic Neuropathy (LHON).,  63  (22): [PMID:33180495] [10.1021/acs.jmedchem.0c00942]

Source

Source(1):

• Scientific Literature