8-((6-Chloropyridin-3-yl)methyl)-4a-methyl-9-nitro-3,4a,6,7,8,9ahexahydro-2H-[1,4]dioxino[2',3':4,5]pyrrolo[1,2-a]imidazole

ID: ALA2288914

PubChem CID: 71518115

Max Phase: Preclinical

Molecular Formula: C15H17ClN4O4

Molecular Weight: 352.78

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CC12OCCOC1C([N+](=O)[O-])=C1N(Cc3ccc(Cl)nc3)CCN12

Standard InChI:  InChI=1S/C15H17ClN4O4/c1-15-13(23-6-7-24-15)12(20(21)22)14-18(4-5-19(14)15)9-10-2-3-11(16)17-8-10/h2-3,8,13H,4-7,9H2,1H3

Standard InChI Key:  BVLVDJKRMPWGSJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   19.2531   -9.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5059   -9.8717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5899  -10.6821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3924  -10.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8010  -10.1437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6617   -8.8282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4601   -8.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5442   -9.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1193   -8.5188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2914  -10.1437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9547   -9.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8666   -8.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3274   -8.0850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8075   -7.4218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5169   -7.9969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5442  -10.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7968   -9.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3827   -9.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0918   -9.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0918  -10.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3827  -11.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6736  -10.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6736   -9.8717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9687  -11.0975    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  5  1  0
  6  7  1  0
  7  8  1  0
 10 11  1  0
 11 12  1  0
  9 12  1  0
  7  9  1  0
  8 10  1  0
  5  8  1  0
  1  6  2  0
 13 14  2  0
 13 15  1  0
  6 13  1  0
  8 16  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 22 24  1  0
 17 19  1  0
  2 17  1  0
M  CHG  2  13   1  15  -1
M  END

Associated Targets(non-human)

Aphis craccivora (935 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 352.78Molecular Weight (Monoisotopic): 352.0938AlogP: 1.44#Rotatable Bonds: 3
Polar Surface Area: 80.97Molecular Species: NEUTRALHBA: 7HBD:
#RO5 Violations: HBA (Lipinski): 8HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 1.43CX LogP: 1.65CX LogD: 1.65
Aromatic Rings: 1Heavy Atoms: 24QED Weighted: 0.46Np Likeness Score: -0.81

References

1. Ye Z, Shi L, Shao X, Xu X, Xu Z, Li Z..  (2013)  Pyrrole- and dihydropyrrole-fused neonicotinoids: design, synthesis, and insecticidal evaluation.,  61  (2): [PMID:23256728] [10.1021/jf3044132]

Source