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

ID: ALA2288922

PubChem CID: 71518282

Max Phase: Preclinical

Molecular Formula: C16H23ClN4O4

Molecular Weight: 370.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC1C([N+](=O)[O-])=C(N(CC)Cc2ccc(Cl)nc2)N(C)C1(C)O

Standard InChI:  InChI=1S/C16H23ClN4O4/c1-5-20(10-11-7-8-12(17)18-9-11)15-13(21(23)24)14(25-6-2)16(3,22)19(15)4/h7-9,14,22H,5-6,10H2,1-4H3

Standard InChI Key:  KJUPSCHIFMZADG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
   12.4535  -17.0155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2389  -17.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2389  -18.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4535  -18.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9733  -17.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0535  -17.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2029  -19.1234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4004  -19.2983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7180  -19.7596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4056  -16.4635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2029  -16.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9022  -18.5716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6536  -18.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1520  -17.6788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7393  -16.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9180  -16.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7393  -18.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094  -17.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9180  -18.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5094  -19.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6880  -19.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2753  -18.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6880  -17.6788    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4540  -18.3879    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.3176  -18.7235    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
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288922

   5-[(6-chloropyridin-3-yl)methyl-ethylamino]-3-ethoxy-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: 370.84

Molecular Weight (Monoisotopic): 370.1408

AlogP: 2.06

#Rotatable Bonds: 7

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: 2.06

CX LogD: 2.06

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.45

Np Likeness Score: -0.75

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