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

ID: ALA4537208

PubChem CID: 155548400

Max Phase: Preclinical

Molecular Formula: C20H16Cl2O4

Molecular Weight: 391.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CCCC(O)=C1C(=O)c1cccc(OCc2ccc(Cl)cc2Cl)c1

Standard InChI:  InChI=1S/C20H16Cl2O4/c21-14-8-7-13(16(22)10-14)11-26-15-4-1-3-12(9-15)20(25)19-17(23)5-2-6-18(19)24/h1,3-4,7-10,23H,2,5-6,11H2

Standard InChI Key:  QGQPYTHJRDGLHZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   23.2762   -9.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2750   -9.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9831  -10.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6927   -9.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6899   -9.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9813   -8.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5683   -8.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5681   -7.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8607   -9.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1511   -8.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4456   -9.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4416   -9.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1492  -10.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8609   -9.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1544   -7.9466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5678  -10.4003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3960   -8.7641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1053   -9.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8115   -8.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5191   -9.1680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2248   -8.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2222   -7.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5079   -7.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8052   -7.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5202   -9.9852    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.9278   -7.5272    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3  4  2  0
  4  5  1  0
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  7  8  2  0
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  5 17  1  0
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 20 21  1  0
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 23 24  2  0
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 20 25  1  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4537208

   ---

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: 391.25

Molecular Weight (Monoisotopic): 390.0426

AlogP: 5.32

#Rotatable Bonds: 5

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.41

CX Basic pKa: ┄

CX LogP: 4.78

CX LogD: 1.89

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -0.57

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