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

ID: ALA2229742

PubChem CID: 44245980

Max Phase: Preclinical

Molecular Formula: C22H22ClN3O6S

Molecular Weight: 491.95

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H22ClN3O6S/c1-31-12-11-24-21(27)19-18(14-33(29,30)17-9-7-16(23)8-10-17)26-32-20(19)22(28)25-13-15-5-3-2-4-6-15/h2-10H,11-14H2,1H3,(H,24,27)(H,25,28)

Standard InChI Key:  NCPDKNNLMCROJS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   31.1270  -20.0378    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.2143  -19.2174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4602  -19.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4331  -19.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2581  -19.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5150  -18.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8456  -18.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1806  -18.6742    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9473  -20.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7423  -20.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4058  -20.8795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5629  -20.0410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2999  -18.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9123  -18.9732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4725  -17.6135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6972  -18.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3095  -19.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1329  -20.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7444  -20.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5304  -20.3767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7014  -19.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0885  -19.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0470  -20.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6412  -20.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8201  -20.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3345  -21.2849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6690  -22.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4939  -22.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9758  -21.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7106  -21.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1948  -22.1303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.8583  -22.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1841  -22.7074    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:

   

   ALA2229742

   5-N-benzyl-3-[(4-chlorophenyl)sulfonylmethyl]-4-N-(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: 491.95

Molecular Weight (Monoisotopic): 491.0918

AlogP: 2.61

#Rotatable Bonds: 10

Polar Surface Area: 127.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.52

CX Basic pKa: ┄

CX LogP: 1.79

CX LogD: 1.79

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.42

Np Likeness Score: -1.71

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