2-(3-bromo-4-methoxyphenyl)-4-(pyridin-3-ylmethylene)oxazol-5(4H)-one

ID: ALA1091426

PubChem CID: 6032630

Max Phase: Preclinical

Molecular Formula: C16H11BrN2O3

Molecular Weight: 359.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2=N/C(=C\c3cccnc3)C(=O)O2)cc1Br

Standard InChI:  InChI=1S/C16H11BrN2O3/c1-21-14-5-4-11(8-12(14)17)15-19-13(16(20)22-15)7-10-3-2-6-18-9-10/h2-9H,1H3/b13-7-

Standard InChI Key:  BTISEUNLGQBPKF-QPEQYQDCSA-N

Molfile:  

     RDKit          2D

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   -3.4083  -16.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4429  -16.8393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7454  -17.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0128  -16.8968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9821  -16.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6803  -15.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6494  -14.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9199  -14.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2482  -14.9048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5825  -14.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8435  -13.6327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6684  -13.6378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562  -12.9725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2387  -14.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6448  -15.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4690  -15.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8881  -14.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4770  -13.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542  -13.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753  -15.8625    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.7118  -14.4385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1292  -13.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  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
 16 20  1  0
  2  3  1  0
  5  6  2  0
 21 22  1  0
 17 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091426

   (4Z)-2-(3-bromo-4-methoxyphenyl)-4-(pyridin-3-ylmethylidene)-1,3-oxazol-5-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: 359.18

Molecular Weight (Monoisotopic): 357.9953

AlogP: 3.20

#Rotatable Bonds: 3

Polar Surface Area: 60.78

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.68

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.62

Np Likeness Score: -1.16

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