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

ID: ALA2229885

PubChem CID: 44243567

Max Phase: Preclinical

Molecular Formula: C20H26ClN3O5S

Molecular Weight: 455.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCNC(=O)c1onc(CS(=O)(=O)c2ccc(Cl)cc2)c1C(=O)NCCCC

Standard InChI:  InChI=1S/C20H26ClN3O5S/c1-3-5-11-22-19(25)17-16(24-29-18(17)20(26)23-12-6-4-2)13-30(27,28)15-9-7-14(21)8-10-15/h7-10H,3-6,11-13H2,1-2H3,(H,22,25)(H,23,26)

Standard InChI Key:  ISDRBPMWHFOYQT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 31  0  0  0  0  0  0  0  0999 V2000
   20.7125  -18.6871    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9584  -19.0218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6252  -19.5075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0213  -18.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8463  -18.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1030  -17.3204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4338  -16.8337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7687  -17.3204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.5355  -18.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8881  -17.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5004  -17.6194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0607  -16.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3304  -18.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9940  -19.5259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1510  -18.6872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3805  -17.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8696  -17.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5357  -16.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7145  -16.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2283  -17.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5649  -17.8461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2854  -17.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8977  -17.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6827  -17.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4781  -20.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1417  -20.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6258  -21.6152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3789  -15.6697    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.2894  -22.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2951  -18.2175    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:

   

   ALA2229885

   4-N,5-N-dibutyl-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: 455.96

Molecular Weight (Monoisotopic): 455.1282

AlogP: 3.36

#Rotatable Bonds: 11

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: 2.76

CX LogD: 2.76

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: -1.43

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