3-hydroxy-2-(3-(4-methylbenzyloxy)-2-nitrobenzoyl)cyclohex-2-en-1-one

ID: ALA4540372

PubChem CID: 155549789

Max Phase: Preclinical

Molecular Formula: C21H19NO6

Molecular Weight: 381.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc(COc2cccc(C(=O)C3=C(O)CCCC3=O)c2[N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C21H19NO6/c1-13-8-10-14(11-9-13)12-28-18-7-2-4-15(20(18)22(26)27)21(25)19-16(23)5-3-6-17(19)24/h2,4,7-11,23H,3,5-6,12H2,1H3

Standard InChI Key:  SZUCMFOFSRCRFD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   10.7267   -4.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5648   -3.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5636   -4.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2717   -5.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9813   -4.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9785   -3.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2699   -3.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8570   -3.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8568   -2.5796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1494   -3.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4397   -3.3901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7342   -3.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4378   -5.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1495   -4.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4431   -2.5729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8564   -5.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6847   -3.3904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3939   -3.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1001   -3.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8078   -3.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5134   -3.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5108   -2.5658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7966   -2.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0938   -2.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2675   -2.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2164   -2.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9739   -2.1685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5585   -2.1727    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:

   

   ALA4540372

   ---

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: 381.38

Molecular Weight (Monoisotopic): 381.1212

AlogP: 4.23

#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: 4.02

CX Basic pKa: ┄

CX LogP: 4.02

CX LogD: 0.88

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.35

Np Likeness Score: -0.31

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