3-((4-chlorophenylsulfonyl)methyl)-N4,N5-bis(2-methoxyethyl)isoxazole-4,5-dicarboxamide

ID: ALA2229737

PubChem CID: 44245626

Max Phase: Preclinical

Molecular Formula: C18H22ClN3O7S

Molecular Weight: 459.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCNC(=O)c1onc(CS(=O)(=O)c2ccc(Cl)cc2)c1C(=O)NCCOC

Standard InChI:  InChI=1S/C18H22ClN3O7S/c1-27-9-7-20-17(23)15-14(22-29-16(15)18(24)21-8-10-28-2)11-30(25,26)13-5-3-12(19)4-6-13/h3-6H,7-11H2,1-2H3,(H,20,23)(H,21,24)

Standard InChI Key:  CEDNTIYKRRFAEA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   30.0201  -18.0366    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.2660  -18.3712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9328  -18.8570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3288  -17.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1538  -17.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4106  -16.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7413  -16.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.0763  -16.6699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8430  -18.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1955  -16.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8078  -16.9689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.3681  -15.6093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6379  -18.1220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3015  -18.8752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.4585  -18.0367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6880  -17.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1772  -16.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8432  -15.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0221  -15.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5359  -16.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8725  -17.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5928  -16.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2051  -17.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9901  -17.0140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7856  -19.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4492  -20.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9333  -20.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6865  -15.0192    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.5968  -21.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1628  -16.2073    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
 19 28  1  0
 27 29  1  0
 24 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229737

   3-[(4-chlorophenyl)sulfonylmethyl]-4-N,5-N-bis(2-methoxyethyl)-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: 459.91

Molecular Weight (Monoisotopic): 459.0867

AlogP: 1.05

#Rotatable Bonds: 11

Polar Surface Area: 136.83

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.51

CX Basic pKa: ┄

CX LogP: 0.02

CX LogD: 0.02

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.48

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