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

ID: ALA2288921

PubChem CID: 71518281

Max Phase: Preclinical

Molecular Formula: C15H21ClN4O4

Molecular Weight: 356.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(Cc1ccc(Cl)nc1)C1=C([N+](=O)[O-])C(OC)C(C)(O)N1C

Standard InChI:  InChI=1S/C15H21ClN4O4/c1-5-19(9-10-6-7-11(16)17-8-10)14-12(20(22)23)13(24-4)15(2,21)18(14)3/h6-8,13,21H,5,9H2,1-4H3

Standard InChI Key:  ABICLSHTKCENCA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    3.9514  -16.5822    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7327  -16.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7327  -17.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9514  -17.9087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4671  -17.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5473  -16.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6967  -18.6900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8942  -18.8649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2159  -19.3262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9035  -16.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6967  -15.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3960  -18.1383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1474  -17.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6458  -17.2454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2331  -16.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117  -16.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2331  -17.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0031  -17.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4117  -17.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0031  -18.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1818  -18.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2313  -17.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1818  -17.2454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0527  -17.9545    0.0000 Cl  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
M  CHG  2   7   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288921

   5-[(6-chloropyridin-3-yl)methyl-ethylamino]-3-methoxy-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: 356.81

Molecular Weight (Monoisotopic): 356.1251

AlogP: 1.67

#Rotatable Bonds: 6

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: 1.71

CX LogD: 1.71

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.47

Np Likeness Score: -0.68

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