2-(3-(4-bromobenzyloxy)-2-nitrobenzoyl)-3-hydroxycyclohex-2-en-1-one

ID: ALA4533679

PubChem CID: 155547096

Max Phase: Preclinical

Molecular Formula: C20H16BrNO6

Molecular Weight: 446.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CCCC(O)=C1C(=O)c1cccc(OCc2ccc(Br)cc2)c1[N+](=O)[O-]

Standard InChI:  InChI=1S/C20H16BrNO6/c21-13-9-7-12(8-10-13)11-28-17-6-1-3-14(19(17)22(26)27)20(25)18-15(23)4-2-5-16(18)24/h1,3,6-10,23H,2,4-5,11H2

Standard InChI Key:  QUIYDFAODLRSRO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    1.1515   -4.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9896   -3.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9885   -4.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6965   -5.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4062   -4.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4033   -3.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6947   -3.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2818   -3.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2816   -2.6498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5742   -3.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -3.4603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1590   -3.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8627   -5.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5743   -4.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8679   -2.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2812   -5.0968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1095   -3.4606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8187   -3.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5249   -3.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2326   -3.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9383   -3.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9356   -2.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2214   -2.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5186   -2.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6923   -2.6494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6412   -2.2237    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.3988   -2.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834   -2.2429    0.0000 O   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
 22 26  1  0
 25 27  1  0
 25 28  2  0
M  CHG  2  25   1  27  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4533679

   ---

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: 446.25

Molecular Weight (Monoisotopic): 445.0161

AlogP: 4.68

#Rotatable Bonds: 6

Polar Surface Area: 106.74

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.00

CX Basic pKa: ┄

CX LogP: 4.28

CX LogD: 1.12

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.30

Np Likeness Score: -0.32

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