1-((6-Chloropyridin-3-yl)methyl)-4a-methyl-10-nitro-1,2,3,4a,6,7,8,9a-octahydro-[1,4]dioxepino[2',3':4,5]pyrrolo[1,2-a]-imidazole

ID: ALA2288915

PubChem CID: 71518116

Max Phase: Preclinical

Molecular Formula: C16H19ClN4O4

Molecular Weight: 366.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC12OCCCOC1C([N+](=O)[O-])=C1N(Cc3ccc(Cl)nc3)CCN12

Standard InChI:  InChI=1S/C16H19ClN4O4/c1-16-14(24-7-2-8-25-16)13(21(22)23)15-19(5-6-20(15)16)10-11-3-4-12(17)18-9-11/h3-4,9,14H,2,5-8,10H2,1H3

Standard InChI Key:  BKTVSXFZPZQEDM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   28.5065   -9.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7588   -9.5061    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8505  -10.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6516  -10.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0602   -9.7755    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9151   -8.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7173   -8.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7977   -9.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2957   -8.0428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5068   -9.8596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2758   -9.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5329   -8.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1243   -8.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5765   -7.7065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.0337   -7.0267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7582   -7.6490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7489  -10.2523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0497   -9.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6308   -9.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3383   -9.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3383  -10.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6326  -10.7397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9277  -10.3318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9277   -9.5207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2140  -10.7455    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
 12 13  1  0
  9 13  1  0
  7  9  1  0
  8 10  1  0
  5  8  1  0
  1  6  2  0
 14 15  2  0
 14 16  1  0
  6 14  1  0
  8 17  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 23 25  1  0
 18 20  1  0
  2 18  1  0
M  CHG  2  14   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288915

   5-[(6-Chloropyridin-3-yl)methyl]-1-methyl-7-nitro-9,13-dioxa-2,5-diazatricyclo[6.5.0.02,6]tridec-6-ene

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: 366.81

Molecular Weight (Monoisotopic): 366.1095

AlogP: 1.83

#Rotatable Bonds: 3

Polar Surface Area: 80.97

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.53

CX LogP: 1.71

CX LogD: 1.71

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.46

Np Likeness Score: -0.80

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

Source(1):

• Scientific Literature