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

ID: ALA1091785

Cas Number: 313971-05-0

PubChem CID: 6516567

Max Phase: Preclinical

Molecular Formula: C15H8ClN3O4

Molecular Weight: 329.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1OC(c2ccc(Cl)c([N+](=O)[O-])c2)=N/C1=C\c1cccnc1

Standard InChI:  InChI=1S/C15H8ClN3O4/c16-11-4-3-10(7-13(11)19(21)22)14-18-12(15(20)23-14)6-9-2-1-5-17-8-9/h1-8H/b12-6-

Standard InChI Key:  UEHRUUYVLMTINQ-SDQBBNPISA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -3.9014  -15.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9026  -16.1440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1878  -16.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4713  -16.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4742  -15.3130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1896  -14.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1920  -14.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4788  -13.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7214  -14.0017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1712  -13.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5859  -12.6736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3923  -12.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0060  -12.2964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4430  -13.7666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101  -14.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3200  -14.9745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0178  -14.5326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807  -13.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2502  -13.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7492  -14.9142    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6777  -13.2589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6406  -12.4347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4100  -13.6388    0.0000 O   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
 17 20  1  0
  2  3  1  0
  5  6  2  0
  9 10  2  0
 21 22  2  0
 21 23  1  0
 18 21  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1091785

   (4Z)-2-(4-chloro-3-nitrophenyl)-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: 329.70

Molecular Weight (Monoisotopic): 329.0203

AlogP: 2.99

#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: 3.17

CX LogD: 3.17

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.37

Np Likeness Score: -1.89

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