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

ID: ALA1091042

PubChem CID: 6030124

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)c(Br)c1

Standard InChI:  InChI=1S/C16H11BrN2O3/c1-21-11-4-5-12(13(17)8-11)15-19-14(16(20)22-15)7-10-3-2-6-18-9-10/h2-9H,1H3/b14-7-

Standard InChI Key:  IYMUJHQOEFTVDN-AUWJEWJLSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   14.3084   -9.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2737  -10.3393    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9712  -10.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7038  -10.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7346   -9.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0364   -9.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0673   -8.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7967   -7.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4685   -8.4048    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1342   -7.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8732   -7.1327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0482   -7.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5604   -6.4725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9554   -7.9180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3615   -8.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1857   -8.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6048   -7.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1937   -7.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3708   -7.2092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9424   -9.3481    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   20.4285   -7.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8458   -7.2269    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
 15 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:

   

   ALA1091042

   2-(2-bromo-4-methoxyphenyl)-4-(pyridin-3-ylmethylene)oxazol-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: 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: -1.11

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