2-(4-methyl-3-nitrophenyl)-4-(pyridin-3-ylmethylene)oxazol-5(4H)-one

ID: ALA1094005

PubChem CID: 5400660

Max Phase: Preclinical

Molecular Formula: C16H11N3O4

Molecular Weight: 309.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C2=N/C(=C\c3cccnc3)C(=O)O2)cc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C16H11N3O4/c1-10-4-5-12(8-14(10)19(21)22)15-18-13(16(20)23-15)7-11-3-2-6-17-9-11/h2-9H,1H3/b13-7-

Standard InChI Key:  NNHQTSOGKHXVBF-QPEQYQDCSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -3.4291  -22.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4638  -23.6977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663  -24.1391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0337  -23.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0029  -22.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7011  -22.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6702  -21.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9408  -21.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2690  -21.7631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033  -21.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643  -20.4910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6893  -20.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1771  -19.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2179  -21.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240  -21.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482  -22.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8673  -21.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4562  -20.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333  -20.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8549  -22.7209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6798  -22.7280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4362  -23.4318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6923  -21.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
  6  7  1  0
 14 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
  8  9  1  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 10 14  1  0
  4  5  1  0
  2  3  1  0
  5  6  2  0
 20 21  2  0
 20 22  1  0
 16 20  1  0
  9 10  2  0
 17 23  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1094005

   2-(4-Methyl-3-nitrophenyl)-4-(3-pyridylmethylene)oxazole-5(4H)-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 309.28

Molecular Weight (Monoisotopic): 309.0750

AlogP: 2.64

#Rotatable Bonds: 3

Polar Surface Area: 94.69

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.68

CX LogP: 3.08

CX LogD: 3.08

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.38

Np Likeness Score: -1.74

References

1. Okamoto M, Takayama K, Shimizu T, Muroya A, Furuya T..  (2010)  Structure-activity relationship of novel DAPK inhibitors identified by structure-based virtual screening.,  18  (7): [PMID:20206532] [10.1016/j.bmc.2010.02.018]

Source

Source(1):

• Scientific Literature