2,6-Dichloro-4-(4-hydroxy-phenylimino)-cyclohexa-2,5-dienone

ID: ALA198157

Max Phase: Preclinical

Molecular Formula: C12H7Cl2NO2

Molecular Weight: 268.10

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Dichlorophenol Indophenol

Canonical SMILES:  O=C1C=CC(=Nc2cc(Cl)c(O)c(Cl)c2)C=C1

Standard InChI:  InChI=1S/C12H7Cl2NO2/c13-10-5-8(6-11(14)12(10)17)15-7-1-3-9(16)4-2-7/h1-6,17H

Standard InChI Key:  FBWADIKARMIWNM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    2.3417   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125   -0.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6917   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0875   -0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -1.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3042    0.0333    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -2.8167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5625   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208    0.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1708   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958    0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    1.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  5  1  0
  5  3  2  0
  6  2  1  0
  7  4  1  0
  8  1  1  0
  9  3  1  0
 10  2  1  0
 11  7  2  0
 12 15  1  0
 13 11  1  0
 14 11  1  0
 15 14  2  0
 16 13  2  0
 17 12  2  0
  4  6  2  0
 16 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA198157

   DICHLOROPHENOL INDOPHENOL

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: 268.10

Molecular Weight (Monoisotopic): 266.9854

AlogP: 3.47

#Rotatable Bonds: 1

Polar Surface Area: 49.66

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.92

CX Basic pKa: 3.86

CX LogP: 4.09

CX LogD: 2.71

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.79

Np Likeness Score: -0.18

References

1. Millet R, Urig S, Jacob J, Amtmann E, Moulinoux JP, Gromer S, Becker K, Davioud-Charvet E..  (2005)  Synthesis of 5-nitro-2-furancarbohydrazides and their cis-diamminedichloroplatinum complexes as bitopic and irreversible human thioredoxin reductase inhibitors.,  48  (22): [PMID:16250662] [10.1021/jm050256l]

2. Dong CK, Patel V, Yang JC, Dvorin JD, Duraisingh MT, Clardy J, Wirth DF..  (2009)  Type II NADH dehydrogenase of the respiratory chain of Plasmodium falciparum and its inhibitors.,  19  (3): [PMID:19097788] [10.1016/j.bmcl.2008.11.071]

Source

Source(1):

• Scientific Literature