1-(5-((2-benzoyl-4-chloro-5-methylphenoxy)methyl)-1,3,4-oxadiazol-2-yl)-4-(3-bromophenyl)-3-chloroazetidin-2-one

ID: ALA2289732

PubChem CID: 76331189

Max Phase: Preclinical

Molecular Formula: C26H18BrCl2N3O4

Molecular Weight: 587.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(OCc2nnc(N3C(=O)C(Cl)C3c3cccc(Br)c3)o2)c(C(=O)c2ccccc2)cc1Cl

Standard InChI:  InChI=1S/C26H18BrCl2N3O4/c1-14-10-20(18(12-19(14)28)24(33)15-6-3-2-4-7-15)35-13-21-30-31-26(36-21)32-23(22(29)25(32)34)16-8-5-9-17(27)11-16/h2-12,22-23H,13H2,1H3

Standard InChI Key:  CFLZLIJXWYUYLO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
   13.3947   -5.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3935   -6.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1079   -7.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8239   -6.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8211   -5.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1061   -5.5797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5428   -7.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5399   -8.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8211   -8.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8220   -9.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5372   -9.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2488   -9.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2527   -8.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2562   -6.8289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5418   -5.5695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5387   -4.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2512   -4.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0318   -4.5829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5145   -3.9140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0330   -3.2473    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2521   -3.5010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3391   -3.9512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8962   -4.5526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9439   -3.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4977   -3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8597   -5.3764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3215   -4.0320    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.9785   -2.5794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7069   -2.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7419   -1.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0453   -0.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3120   -1.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2806   -2.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6806   -5.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6792   -7.2307    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.4716   -0.9820    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  7 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 17  2  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 23 25  1  0
 24 25  1  0
 23 26  2  0
 25 27  1  0
 24 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
  1 34  1  0
  2 35  1  0
 30 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2289732

   1-[5-[(2-Benzoyl-4-chloro-5-methylphenoxy)methyl]-1,3,4-oxadiazol-2-yl]-4-(3-bromophenyl)-3-chloroazetidin-2-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: 587.26

Molecular Weight (Monoisotopic): 584.9858

AlogP: 6.30

#Rotatable Bonds: 7

Polar Surface Area: 85.53

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.15

CX Basic pKa: ┄

CX LogP: 6.09

CX LogD: 6.09

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.14

Np Likeness Score: -1.00

References

1. Khanum SA, Shashikanth S, Sathyanarayana SG, Lokesh S, Deepak SA..  (2009)  Synthesis and antifungal activity of 2-azetidinonyl-5-(2-benzoylphenoxy)methyl-1,3,4-oxadiazoles against seed-borne pathogens of Eleusine coracana (L.) Gaertn.,  65  (7): [PMID:19319825] [10.1002/ps.1752]

Source

Source(1):

• Scientific Literature