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

ID: ALA2227700

PubChem CID: 44245456

Max Phase: Preclinical

Molecular Formula: C18H23N3O7S

Molecular Weight: 425.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCNC(=O)c1onc(CS(=O)(=O)c2ccccc2)c1C(=O)NCCOC

Standard InChI:  InChI=1S/C18H23N3O7S/c1-26-10-8-19-17(22)15-14(12-29(24,25)13-6-4-3-5-7-13)21-28-16(15)18(23)20-9-11-27-2/h3-7H,8-12H2,1-2H3,(H,19,22)(H,20,23)

Standard InChI Key:  OBOHNBYTEZZOFC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   12.6203  -24.8157    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.8662  -25.1503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5330  -25.6360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9290  -24.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7540  -24.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0108  -23.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3415  -22.9623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6764  -23.4490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4432  -24.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7957  -23.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4080  -23.7480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9684  -22.3883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2380  -24.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9017  -25.6543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0587  -24.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2883  -24.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7774  -23.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4434  -22.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6223  -22.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1361  -23.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4728  -23.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1930  -23.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8053  -24.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5903  -23.7931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3858  -26.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0494  -27.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5335  -27.7436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1971  -28.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2026  -24.3461    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
 27 28  1  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2227700

   3-(benzenesulfonylmethyl)-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: 425.46

Molecular Weight (Monoisotopic): 425.1257

AlogP: 0.40

#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: -0.58

CX LogD: -0.59

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -1.47

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