2-(3-(2,4-dichlorobenzyloxy)-2-nitrobenzoyl)-3-hydroxycyclohex-2-en-1-one

ID: ALA4526579

PubChem CID: 155544224

Max Phase: Preclinical

Molecular Formula: C20H15Cl2NO6

Molecular Weight: 436.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CCCC(O)=C1C(=O)c1cccc(OCc2ccc(Cl)cc2Cl)c1[N+](=O)[O-]

Standard InChI:  InChI=1S/C20H15Cl2NO6/c21-12-8-7-11(14(22)9-12)10-29-17-6-1-3-13(19(17)23(27)28)20(26)18-15(24)4-2-5-16(18)25/h1,3,6-9,24H,2,4-5,10H2

Standard InChI Key:  NBUPTYNWLVUUKL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   33.7345   -9.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7334  -10.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4414  -10.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1511  -10.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1483   -9.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4397   -9.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0267   -9.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0265   -8.3702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3191   -9.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6095   -9.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9040   -9.5859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6076  -10.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3193  -10.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6128   -8.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.0262  -10.8171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.8544   -9.1809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.5637   -9.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2699   -9.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9775   -9.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6832   -9.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6806   -8.3563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9663   -7.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2636   -8.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4372   -8.3697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.1437   -7.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7283   -7.9632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.3862   -7.9441    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   37.9786  -10.4021    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
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  8 10  1  0
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 12  1  1  0
  1 13  1  0
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  6 17  1  0
 17 18  1  0
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 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  7 25  1  0
 25 26  1  0
 25 27  2  0
 22 28  1  0
 20 29  1  0
M  CHG  2  25   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4526579

   ---

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: 436.25

Molecular Weight (Monoisotopic): 435.0276

AlogP: 5.23

#Rotatable Bonds: 6

Polar Surface Area: 106.74

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.93

CX Basic pKa: ┄

CX LogP: 4.72

CX LogD: 1.52

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.29

Np Likeness Score: -0.63

References

1. Ndikuryayo F, Kang WM, Wu FX, Yang WC, Yang GF..  (2019)  Hydrophobicity-oriented drug design (HODD) of new human 4-hydroxyphenylpyruvate dioxygenase inhibitors.,  166  [PMID:30684868] [10.1016/j.ejmech.2019.01.032]

Source

Source(1):

• Scientific Literature