1-((6-Chloropyridin-3-yl)methyl)-5-methyl-7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]imidazol-6(5H)-one

ID: ALA2288660

PubChem CID: 71517941

Max Phase: Preclinical

Molecular Formula: C13H13ClN4O3

Molecular Weight: 308.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1C(=O)C([N+](=O)[O-])=C2N(Cc3ccc(Cl)nc3)CCN21

Standard InChI:  InChI=1S/C13H13ClN4O3/c1-8-12(19)11(18(20)21)13-16(4-5-17(8)13)7-9-2-3-10(14)15-6-9/h2-3,6,8H,4-5,7H2,1H3

Standard InChI Key:  OIPZKKJVDIZNPN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    0.7295   -9.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7283  -10.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449  -10.9827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1631  -10.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1603   -9.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4431   -9.3269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0118  -10.9817    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8708   -9.3209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6620   -9.5599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9340  -10.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7602  -10.3252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3212   -9.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9959   -9.5324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6530   -9.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3818   -8.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5598   -8.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0617   -7.6211    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415   -7.7220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3823   -6.8598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8570   -7.5798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4437   -9.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12  9  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 17 18  2  0
 17 19  1  0
 16 17  1  0
 15 20  2  0
 14 21  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288660

   1-[(6-chloropyridin-3-yl)methyl]-5-methyl-7-nitro-3,5-dihydro-2H-pyrrolo[1,2-a]imidazol-6-one

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: 308.73

Molecular Weight (Monoisotopic): 308.0676

AlogP: 1.27

#Rotatable Bonds: 3

Polar Surface Area: 79.58

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.71

CX Basic pKa: ┄

CX LogP: 1.84

CX LogD: 1.81

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.48

Np Likeness Score: -1.10

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