2-(3-(4-chloro-2-fluorobenzyloxy)-2-methylbenzoyl)-3-hydroxy-5-methylcyclohex-2-en-1-one

ID: ALA4518828

PubChem CID: 155541523

Max Phase: Preclinical

Molecular Formula: C22H20ClFO4

Molecular Weight: 402.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(OCc2ccc(Cl)cc2F)cccc1C(=O)C1=C(O)CC(C)CC1=O

Standard InChI:  InChI=1S/C22H20ClFO4/c1-12-8-18(25)21(19(26)9-12)22(27)16-4-3-5-20(13(16)2)28-11-14-6-7-15(23)10-17(14)24/h3-7,10,12,25H,8-9,11H2,1-2H3

Standard InChI Key:  RXJKIJRWMTVWDI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   21.0158  -26.1749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8540  -25.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8528  -26.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5609  -26.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2705  -26.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2677  -25.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5591  -24.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1462  -24.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1460  -24.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4385  -25.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7289  -24.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0234  -25.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7270  -26.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4387  -26.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7322  -24.1377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1456  -26.5914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9739  -24.9552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6831  -25.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3893  -24.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0969  -25.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8026  -24.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8000  -24.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0858  -23.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3830  -24.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5566  -24.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0980  -26.1764    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   29.5056  -23.7183    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.3057  -26.5791    0.0000 C   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
  6  7  2  0
  7  2  1  0
  2  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 10 14  1  0
 11 12  1  0
 12  1  1  0
  1 13  1  0
 13 14  1  0
 11 15  1  0
 14 16  2  0
  6 17  1  0
 17 18  1  0
 18 19  1  0
 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
 20 26  1  0
 22 27  1  0
  1 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4518828

   ---

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: 402.85

Molecular Weight (Monoisotopic): 402.1034

AlogP: 5.36

#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: 4.47

CX Basic pKa: ┄

CX LogP: 5.11

CX LogD: 2.28

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -0.59

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