2-(3-(4-bromo-2-fluorobenzyloxy)benzoyl)-3-hydroxy-5-methylcyclohex-2-en-1-one

ID: ALA4538931

PubChem CID: 155549396

Max Phase: Preclinical

Molecular Formula: C21H18BrFO4

Molecular Weight: 433.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1CC(=O)C(C(=O)c2cccc(OCc3ccc(Br)cc3F)c2)=C(O)C1

Standard InChI:  InChI=1S/C21H18BrFO4/c1-12-7-18(24)20(19(25)8-12)21(26)13-3-2-4-16(9-13)27-11-14-5-6-15(22)10-17(14)23/h2-6,9-10,12,24H,7-8,11H2,1H3

Standard InChI Key:  SMFUYNAVHXQTTP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   14.4067  -14.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4056  -15.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1136  -15.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8233  -15.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8205  -14.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1118  -14.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6989  -14.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6987  -13.3930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9913  -14.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2817  -14.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5762  -14.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5721  -15.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2798  -15.8369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9915  -15.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2850  -13.3863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6983  -15.8400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5266  -14.2037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2359  -14.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9420  -14.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6497  -14.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3554  -14.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3528  -13.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6385  -12.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9358  -13.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6507  -15.4249    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.0584  -12.9669    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.8630  -15.8324    0.0000 C   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
 12 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538931

   ---

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: 433.27

Molecular Weight (Monoisotopic): 432.0372

AlogP: 5.16

#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: 4.38

CX Basic pKa: ┄

CX LogP: 4.77

CX LogD: 1.86

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.58

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