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

ID: ALA2229743

PubChem CID: 44245979

Max Phase: Preclinical

Molecular Formula: C22H20ClN3O5S

Molecular Weight: 473.94

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H20ClN3O5S/c1-2-12-24-21(27)19-18(14-32(29,30)17-10-8-16(23)9-11-17)26-31-20(19)22(28)25-13-15-6-4-3-5-7-15/h2-11H,1,12-14H2,(H,24,27)(H,25,28)

Standard InChI Key:  QWLAPRYIQLFWGM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    3.7854  -25.2043    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8727  -24.3840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1186  -24.7185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0915  -24.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9165  -24.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1734  -23.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5040  -23.3539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8391  -23.8406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058  -25.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4007  -25.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0642  -26.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2213  -25.2076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9583  -23.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5707  -24.1397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1310  -22.7801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3556  -23.8859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9680  -24.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7913  -25.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4028  -25.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1887  -25.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3598  -24.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7469  -24.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7055  -25.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997  -25.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785  -25.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9929  -26.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3275  -27.2065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1523  -27.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6344  -26.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3690  -26.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8426  -27.8740    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8532  -27.2968    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
 27 31  1  0
 30 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229743

   5-N-benzyl-3-[(4-chlorophenyl)sulfonylmethyl]-4-N-prop-2-enyl-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: 473.94

Molecular Weight (Monoisotopic): 473.0812

AlogP: 3.15

#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: 10.53

CX Basic pKa: ┄

CX LogP: 2.57

CX LogD: 2.57

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -1.63

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