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

ID: ALA4539445

PubChem CID: 155550052

Max Phase: Preclinical

Molecular Formula: C21H17BrFNO6

Molecular Weight: 478.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1CC(=O)C(C(=O)c2cccc(OCc3ccc(Br)cc3F)c2[N+](=O)[O-])=C(O)C1

Standard InChI:  InChI=1S/C21H17BrFNO6/c1-11-7-16(25)19(17(26)8-11)21(27)14-3-2-4-18(20(14)24(28)29)30-10-12-5-6-13(22)9-15(12)23/h2-6,9,11,25H,7-8,10H2,1H3

Standard InChI Key:  YEZZWVHFOGNZSB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   21.9156  -10.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7537   -9.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7526  -10.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4606  -10.7293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1703  -10.3199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1674   -9.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4588   -9.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0459   -9.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0457   -8.2752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3383   -9.5012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6286   -9.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9231   -9.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6267  -10.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3384  -10.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6320   -8.2685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0453  -10.7222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8736   -9.0860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5828   -9.4919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2890   -9.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9967   -9.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7024   -9.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6997   -8.2613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9855   -7.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2827   -8.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4564   -8.2748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.1629   -7.8641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7474   -7.8683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4053   -7.8491    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   28.9977  -10.3072    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.2054  -10.7099    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
 25 26  1  0
 25 27  2  0
 22 28  1  0
 20 29  1  0
  1 30  1  0
M  CHG  2  25   1  26  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4539445

   ---

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: 478.27

Molecular Weight (Monoisotopic): 477.0223

AlogP: 5.07

#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: 3.92

CX Basic pKa: ┄

CX LogP: 4.71

CX LogD: 1.50

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.27

Np Likeness Score: -0.64

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