5,6-Dibutoxy-1-((6-chloropyridin-3-yl)methyl)-5-methyl-7-nitro-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazole

ID: ALA2288659

PubChem CID: 71517946

Max Phase: Preclinical

Molecular Formula: C21H31ClN4O4

Molecular Weight: 438.96

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOC1C([N+](=O)[O-])=C2N(Cc3ccc(Cl)nc3)CCN2C1(C)OCCCC

Standard InChI:  InChI=1S/C21H31ClN4O4/c1-4-6-12-29-19-18(26(27)28)20-24(15-16-8-9-17(22)23-14-16)10-11-25(20)21(19,3)30-13-7-5-2/h8-9,14,19H,4-7,10-13,15H2,1-3H3

Standard InChI Key:  DSNLCBAXISCKKS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   32.2037   -4.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7788   -6.6228    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   33.6332   -4.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4230   -5.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   36.1400   -3.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3193   -3.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8220   -3.2678    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0032   -3.3685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   36.8160   -5.3897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.1187   -4.2620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4364   -3.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6410   -5.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7840   -4.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0532   -4.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6060   -4.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8782   -4.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2911   -5.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0803   -3.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  6  1  1  0
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  5  8  1  0
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  9 10  1  0
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 16 12  2  0
 17 18  2  0
 17 19  1  0
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 15 20  1  0
 14 21  1  0
 14 22  1  0
 20 23  1  0
 21 24  1  0
 23 25  1  0
 24 26  1  0
 25 27  1  0
 26 28  1  0
 28 29  1  0
 27 30  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288659

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

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: 438.96

Molecular Weight (Monoisotopic): 438.2034

AlogP: 4.03

#Rotatable Bonds: 11

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: 1.82

CX LogP: 4.47

CX LogD: 4.47

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.22

Np Likeness Score: -0.57

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