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

ID: ALA2229876

PubChem CID: 44244779

Max Phase: Preclinical

Molecular Formula: C18H22ClN3O5S

Molecular Weight: 427.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCNC(=O)c1onc(CSc2ccc(Cl)cc2)c1C(=O)NCCOC

Standard InChI:  InChI=1S/C18H22ClN3O5S/c1-25-9-7-20-17(23)15-14(11-28-13-5-3-12(19)4-6-13)22-27-16(15)18(24)21-8-10-26-2/h3-6H,7-11H2,1-2H3,(H,20,23)(H,21,24)

Standard InChI Key:  GYNSFQCRFYQIIB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.0873   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9123   -2.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1691   -1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4998   -1.3709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8348   -1.8576    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6015   -3.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7812   -3.2212    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.9541   -1.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5664   -2.1566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1267   -0.7969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3965   -3.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0600   -4.0629    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2170   -3.2244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4466   -2.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3514   -1.9027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9637   -2.4556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7487   -2.2017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5442   -4.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2077   -5.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6919   -6.1522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9357   -1.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6018   -1.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7806   -0.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2945   -1.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6311   -2.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4450   -0.2069    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.3555   -6.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3610   -2.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  1  6  1  0
  6  7  1  0
  3  8  1  0
  8  9  1  0
  8 10  2  0
  2 11  1  0
 11 12  1  0
 11 13  2  0
  7 14  1  0
  9 15  1  0
 15 16  1  0
 16 17  1  0
 12 18  1  0
 18 19  1  0
 19 20  1  0
 14 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 14  1  0
 23 26  1  0
 20 27  1  0
 17 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229876

   3-[(4-chlorophenyl)sulfanylmethyl]-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: 427.91

Molecular Weight (Monoisotopic): 427.0969

AlogP: 2.37

#Rotatable Bonds: 11

Polar Surface Area: 102.69

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.55

CX Basic pKa: ┄

CX LogP: 1.04

CX LogD: 1.04

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -1.52

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