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

ID: ALA2288923

PubChem CID: 71518283

Max Phase: Preclinical

Molecular Formula: C17H25ClN4O4

Molecular Weight: 384.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOC1C([N+](=O)[O-])=C(N(CC)Cc2ccc(Cl)nc2)N(C)C1(C)O

Standard InChI:  InChI=1S/C17H25ClN4O4/c1-5-9-26-15-14(22(24)25)16(20(4)17(15,3)23)21(6-2)11-12-7-8-13(18)19-10-12/h7-8,10,15,23H,5-6,9,11H2,1-4H3

Standard InChI Key:  ZSYFDJMHUUBBIL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
   22.1194  -16.8215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9049  -17.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9049  -17.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1194  -18.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6352  -17.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7194  -17.1602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8648  -18.9294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0622  -19.1043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3839  -19.5656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0715  -16.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8648  -16.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5640  -18.3777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3155  -18.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8138  -17.4848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4052  -16.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5839  -16.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4052  -18.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1712  -17.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5839  -18.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1712  -18.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3499  -18.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9413  -18.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3499  -17.4848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1200  -18.1939    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   24.9794  -18.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7310  -18.1951    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
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288923

   5-[(6-chloropyridin-3-yl)methyl-ethylamino]-1,2-dimethyl-4-nitro-3-propoxy-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: 384.86

Molecular Weight (Monoisotopic): 384.1564

AlogP: 2.45

#Rotatable Bonds: 8

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: 2.59

CX LogD: 2.59

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.42

Np Likeness Score: -0.85

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