3-Butoxy-5-(((6-chloropyridin-3-yl)methyl)(ethyl)amino)-1,2-dimethyl-4-nitro-2,3-dihydro-1H-pyrrol-2-ol

ID: ALA2288925

PubChem CID: 71518285

Max Phase: Preclinical

Molecular Formula: C18H27ClN4O4

Molecular Weight: 398.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOC1C([N+](=O)[O-])=C(N(CC)Cc2ccc(Cl)nc2)N(C)C1(C)O

Standard InChI:  InChI=1S/C18H27ClN4O4/c1-5-7-10-27-16-15(23(25)26)17(21(4)18(16,3)24)22(6-2)12-13-8-9-14(19)20-11-13/h8-9,11,16,24H,5-7,10,12H2,1-4H3

Standard InChI Key:  DPCYMSIIVSZILS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    5.4413  -21.0561    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2268  -21.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2268  -22.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4413  -22.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9612  -21.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0413  -21.3948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1908  -23.1640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3882  -23.3388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7099  -23.8001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3934  -20.5041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1908  -20.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8900  -22.6122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6415  -22.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398  -21.7193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7271  -21.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9058  -21.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7271  -22.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972  -21.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9058  -22.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972  -23.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759  -23.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2632  -22.4284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759  -21.7193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4418  -22.4284    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.3054  -22.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0570  -22.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7168  -22.9159    0.0000 C   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  2  0
  1  5  1  0
  2  6  1  0
  7  8  2  0
  7  9  1  0
  4  7  1  0
  2 10  1  0
  1 11  1  0
 12 13  1  0
  3 12  1  0
 15 16  1  0
 14 15  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
 14 17  1  0
  5 14  1  0
 13 25  1  0
 25 26  1  0
 26 27  1  0
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288925

   3-butoxy-5-[(6-chloropyridin-3-yl)methyl-ethylamino]-1,2-dimethyl-4-nitro-3H-pyrrol-2-ol

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: 398.89

Molecular Weight (Monoisotopic): 398.1721

AlogP: 2.84

#Rotatable Bonds: 9

Polar Surface Area: 91.97

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: 2.16

CX LogP: 3.03

CX LogD: 3.03

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.30

Np Likeness Score: -0.74

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