3-(phenylsulfonylmethyl)-N4,N5-dipropylisoxazole-4,5-dicarboxamide

ID: ALA2229883

PubChem CID: 44243563

Max Phase: Preclinical

Molecular Formula: C18H23N3O5S

Molecular Weight: 393.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNC(=O)c1onc(CS(=O)(=O)c2ccccc2)c1C(=O)NCCC

Standard InChI:  InChI=1S/C18H23N3O5S/c1-3-10-19-17(22)15-14(21-26-16(15)18(23)20-11-4-2)12-27(24,25)13-8-6-5-7-9-13/h5-9H,3-4,10-12H2,1-2H3,(H,19,22)(H,20,23)

Standard InChI Key:  RIEARTCKUAEYNW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    2.8496  -17.6241    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0955  -17.9587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7623  -18.4445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1582  -17.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9832  -17.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2400  -16.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5707  -15.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9057  -16.2574    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6725  -17.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250  -16.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6374  -16.5564    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1977  -15.1968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4674  -17.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1309  -18.4628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2879  -17.6242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175  -16.8670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066  -16.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6728  -15.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8515  -15.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3654  -16.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020  -16.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4223  -16.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0347  -16.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8196  -16.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6151  -19.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2787  -19.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7628  -20.5520    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
  6 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  0
 13 14  1  0
 13 15  2  0
  1 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 11 22  1  0
 22 23  1  0
 23 24  1  0
 14 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229883

   3-(benzenesulfonylmethyl)-4-N,5-N-dipropyl-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: 393.47

Molecular Weight (Monoisotopic): 393.1358

AlogP: 1.93

#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: 1.27

CX LogD: 1.27

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.67

Np Likeness Score: -1.49

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