N5-benzyl-N4-butyl-3-((4-chlorophenylsulfonyl)methyl)isoxazole-4,5-dicarboxamide

ID: ALA2229745

PubChem CID: 44245981

Max Phase: Preclinical

Molecular Formula: C23H24ClN3O5S

Molecular Weight: 489.98

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCNC(=O)c1c(CS(=O)(=O)c2ccc(Cl)cc2)noc1C(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C23H24ClN3O5S/c1-2-3-13-25-22(28)20-19(15-33(30,31)18-11-9-17(24)10-12-18)27-32-21(20)23(29)26-14-16-7-5-4-6-8-16/h4-12H,2-3,13-15H2,1H3,(H,25,28)(H,26,29)

Standard InChI Key:  LYSVUBQALCIXFJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   21.1147  -25.4212    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.2020  -24.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4479  -24.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4208  -24.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2458  -24.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5026  -24.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8333  -23.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1682  -24.0576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9350  -25.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7299  -25.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3935  -26.2630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5506  -25.4245    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2876  -23.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8999  -24.3566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4602  -22.9970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6849  -24.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2972  -24.6557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1205  -25.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7321  -26.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5181  -25.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6890  -24.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0761  -24.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0347  -26.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6289  -26.0880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8078  -26.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3221  -26.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6567  -27.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4816  -27.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9635  -26.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6983  -26.8457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1824  -27.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8460  -28.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1718  -28.0909    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  4  2  0
  4  9  1  0
  9  1  1  0
  5 10  1  0
 10 11  2  0
 10 12  1  0
  6 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 12 23  1  0
  1 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 23 30  1  0
 30 31  1  0
 31 32  1  0
 27 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229745

   5-N-benzyl-4-N-butyl-3-[(4-chlorophenyl)sulfonylmethyl]-1,2-oxazole-4,5-dicarboxamide

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: 489.98

Molecular Weight (Monoisotopic): 489.1125

AlogP: 3.76

#Rotatable Bonds: 10

Polar Surface Area: 118.37

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.53

CX Basic pKa: ┄

CX LogP: 3.16

CX LogD: 3.16

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: -1.58

References

1. Yu GJ, Iwamoto S, Robins LI, Fettinger JC, Sparks TC, Lorsbach BA, Kurth MJ..  (2009)  3-(Arylthiomethyl)isoxazole-4,5-dicarboxamides: chemoselective nucleophilic chemistry and insecticidal activity.,  57  (16): [PMID:19624156] [10.1021/jf901512t]

Source

Source(1):

• Scientific Literature