2-[(E)-2-(4-nitrophenyl)ethenyl]quinazolin-4(3H)-one

ID: ALA4539405

PubChem CID: 135446762

Max Phase: Preclinical

Molecular Formula: C16H11N3O3

Molecular Weight: 293.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1[nH]c(/C=C/c2ccc([N+](=O)[O-])cc2)nc2ccccc12

Standard InChI:  InChI=1S/C16H11N3O3/c20-16-13-3-1-2-4-14(13)17-15(18-16)10-7-11-5-8-12(9-6-11)19(21)22/h1-10H,(H,17,18,20)/b10-7+

Standard InChI Key:  ZRKBGTUWFGKHKQ-JXMROGBWSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   32.4056  -13.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4044  -14.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8193  -13.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1107  -13.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8221  -14.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1129  -14.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1085  -15.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8116  -16.0027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5208  -15.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5269  -14.7804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3980  -15.9928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2259  -16.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9362  -15.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6413  -16.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6335  -16.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3377  -17.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3469  -15.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0517  -16.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0510  -16.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7593  -17.2559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.4688  -16.8504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.7557  -18.0731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  6  1  0
  5  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  7 11  2  0
  9 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 19  2  0
 18 17  2  0
 17 14  1  0
 18 19  1  0
 20 21  2  0
 20 22  1  0
 19 20  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4539405

   ---

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: 293.28

Molecular Weight (Monoisotopic): 293.0800

AlogP: 3.00

#Rotatable Bonds: 3

Polar Surface Area: 88.89

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.96

CX Basic pKa: 4.68

CX LogP: 3.07

CX LogD: 3.07

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.59

Np Likeness Score: -1.00

References

1. Mularski J, Malarz K, Pacholczyk M, Musiol R..  (2019)  The p53 stabilizing agent CP-31398 and multi-kinase inhibitors. Designing, synthesizing and screening of styrylquinazoline series.,  163  [PMID:30562697] [10.1016/j.ejmech.2018.12.012]

2. Zheng L, Ren R, Sun X, Zou Y, Shi Y, Di B, Niu MM..  (2021)  Discovery of a Dual Tubulin and Poly(ADP-Ribose) Polymerase-1 Inhibitor by Structure-Based Pharmacophore Modeling, Virtual Screening, Molecular Docking, and Biological Evaluation.,  64  (21.0): [PMID:34670362] [10.1021/acs.jmedchem.1c00932]

3. Parshuram Satpute D, Shirwadkar U, Kumar Tharalla A, Dattatray Shinde S, Nikhil Vaidya G, Joshi S, Patel Vatsa P, Jain A, Singh AA, Garg R, Mandoli A, Kumar D..  (2023)  Discovery of fluorinated 2‑Styryl 4(3H)-quinazolinone as potential therapeutic hit for oral cancer.,  81  [PMID:36796126] [10.1016/j.bmc.2023.117193]

Source

Source(1):

• Scientific Literature