N5-benzyl-3-(phenylsulfonylmethyl)-N4-propylisoxazole-4,5-dicarboxamide

ID: ALA2229741

PubChem CID: 44245797

Max Phase: Preclinical

Molecular Formula: C22H23N3O5S

Molecular Weight: 441.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNC(=O)c1c(CS(=O)(=O)c2ccccc2)noc1C(=O)NCc1ccccc1

Standard InChI:  InChI=1S/C22H23N3O5S/c1-2-13-23-21(26)19-18(15-31(28,29)17-11-7-4-8-12-17)25-30-20(19)22(27)24-14-16-9-5-3-6-10-16/h3-12H,2,13-15H2,1H3,(H,23,26)(H,24,27)

Standard InChI Key:  UDYFPBJMXAYXNS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   21.4527  -19.6676    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.5400  -18.8472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7859  -19.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7589  -19.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5839  -19.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8408  -18.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1714  -17.8171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5063  -18.3039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2731  -19.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0680  -19.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7316  -20.5093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8887  -19.6708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6257  -18.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2380  -18.6030    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7984  -17.2432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0231  -18.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6354  -18.9020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4588  -19.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0703  -20.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8563  -20.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0272  -19.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4144  -18.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3728  -20.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9669  -20.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1458  -20.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6602  -20.9147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9947  -21.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8196  -21.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3016  -21.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0364  -21.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5205  -21.7601    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA2229741

   3-(benzenesulfonylmethyl)-5-N-benzyl-4-N-propyl-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: 441.51

Molecular Weight (Monoisotopic): 441.1358

AlogP: 2.72

#Rotatable Bonds: 9

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: 10.54

CX Basic pKa: ┄

CX LogP: 2.11

CX LogD: 2.11

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.53

Np Likeness Score: -1.55

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