2-(3-(4-chloro-2-fluorobenzyloxy)benzoyl)-3-hydroxycyclohex-2-en-1-one

ID: ALA4549115

PubChem CID: 155549408

Max Phase: Preclinical

Molecular Formula: C20H16ClFO4

Molecular Weight: 374.80

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CCCC(O)=C1C(=O)c1cccc(OCc2ccc(Cl)cc2F)c1

Standard InChI:  InChI=1S/C20H16ClFO4/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:  HJVKUZDPBRBQPX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    4.0433  -14.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0421  -15.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7502  -15.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4598  -15.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4570  -14.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7484  -14.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3355  -14.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3353  -13.5086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6278  -14.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182  -14.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2127  -14.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2087  -15.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9163  -15.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6280  -15.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9215  -13.5018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3349  -15.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1632  -14.3193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8724  -14.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5786  -14.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2862  -14.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9919  -14.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9893  -13.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2751  -13.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5723  -13.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2873  -15.5405    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.6949  -13.0825    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  0
 14 16  2  0
  5 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
 20 25  1  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4549115

   ---

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: 374.80

Molecular Weight (Monoisotopic): 374.0721

AlogP: 4.81

#Rotatable Bonds: 5

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.35

CX Basic pKa: ┄

CX LogP: 4.31

CX LogD: 1.39

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.60

Np Likeness Score: -0.76

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