1-((6-Chloropyridin-3-yl)methyl)-4a-methyl-11-nitro-2,3,4a,6,7,8,9,10a-octahydro-1H-[1,4]dioxocino[2',3':4,5]pyrrolo-[1,2-a]imidazole

ID: ALA2288916

PubChem CID: 71518117

Max Phase: Preclinical

Molecular Formula: C17H21ClN4O4

Molecular Weight: 380.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC12OCCCCOC1C([N+](=O)[O-])=C1N(Cc3ccc(Cl)nc3)CCN12

Standard InChI:  InChI=1S/C17H21ClN4O4/c1-17-15(25-8-2-3-9-26-17)14(22(23)24)16-20(6-7-21(16)17)11-12-4-5-13(18)19-10-12/h4-5,10,15H,2-3,6-9,11H2,1H3

Standard InChI Key:  LIWJOYWXVRGGHK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   37.2517   -8.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4657   -9.0291    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4657   -9.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2383  -10.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7230   -9.4502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.7364   -8.1278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5090   -8.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5090   -9.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0859   -7.8075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.0784   -9.8086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.9092   -9.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4942   -9.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4942   -8.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.9133   -7.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4843   -7.3439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.0627   -6.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.6992   -7.1509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.3072   -9.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8143   -8.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4057   -8.3841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0626   -8.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9720   -9.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2203  -10.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5635   -9.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6582   -8.7086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8159   -9.8465    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
 13 14  1  0
  9 14  1  0
  7  9  1  0
  8 10  1  0
  5  8  1  0
  1  6  2  0
 15 16  2  0
 15 17  1  0
  6 15  1  0
  8 18  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 24 26  1  0
 19 21  1  0
  2 19  1  0
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288916

   5-[(6-Chloropyridin-3-yl)methyl]-1-methyl-7-nitro-9,14-dioxa-2,5-diazatricyclo[6.6.0.02,6]tetradec-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: 380.83

Molecular Weight (Monoisotopic): 380.1251

AlogP: 2.22

#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: 1.56

CX LogP: 2.23

CX LogD: 2.23

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: -0.68

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