3-hydroxy-2-(2-nitro-4-(trifluoromethyl)benzoyl)cyclohex-2-enone

ID: ALA4567229

Max Phase: Preclinical

Molecular Formula: C14H10F3NO5

Molecular Weight: 329.23

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1CCCC(O)=C1C(=O)c1ccc(C(F)(F)F)cc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,19H,1-3H2

Standard InChI Key:  ISNCJIAYWFSKHQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    4.2579   -3.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2567   -4.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9648   -4.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6744   -4.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6716   -3.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9630   -3.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5501   -3.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -2.1958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425   -3.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1328   -3.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4273   -3.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4233   -4.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1309   -4.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8426   -4.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -2.1891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5495   -4.6428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9606   -2.1954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6670   -1.7847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2516   -1.7889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3828   -4.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3841   -5.4652    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0899   -4.2383    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0865   -5.0559    0.0000 F   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
  6 17  1  0
 17 18  1  0
 17 19  2  0
  4 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
M  CHG  2  17   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4567229

   ---

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: 329.23

Molecular Weight (Monoisotopic): 329.0511

AlogP: 3.36

#Rotatable Bonds: 3

Polar Surface Area: 97.51

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.49

CX Basic pKa: ┄

CX LogP: 2.82

CX LogD: -0.56

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.40

Np Likeness Score: -0.69

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