(Z)-(+)-4-[[(6-chloro-3-pyridinyl)methyl]ethylamino]-1-(1-phenyl)ethyl-3-methyl-5-nitro-1,2,3,6-tetrahydropyrimidine

ID: ALA2251834

PubChem CID: 76308259

Max Phase: Preclinical

Molecular Formula: C21H26ClN5O2

Molecular Weight: 415.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(Cc1ccc(Cl)nc1)C1=C([N+](=O)[O-])CN(C(C)c2ccccc2)CN1C

Standard InChI:  InChI=1S/C21H26ClN5O2/c1-4-25(13-17-10-11-20(22)23-12-17)21-19(27(28)29)14-26(15-24(21)3)16(2)18-8-6-5-7-9-18/h5-12,16H,4,13-15H2,1-3H3

Standard InChI Key:  GSLCCWKXRCGUBW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   10.4487   -8.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4476   -9.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1556   -9.8502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8653   -9.4408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8625   -8.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1538   -8.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7395   -9.8493    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.5686   -8.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2779   -8.6128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9840   -8.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6958   -8.6124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3999   -8.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4010   -7.3871    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6919   -6.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9817   -7.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809   -9.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5748   -9.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6964   -9.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2723   -6.9794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5651   -7.3888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2714   -6.1622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1087   -6.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8164   -7.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8116   -8.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5184   -8.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2271   -8.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2245   -7.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5171   -6.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1087   -6.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 15  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  9 16  1  0
 16 17  1  0
 11 18  1  0
 19 20  2  0
 19 21  1  0
 15 19  1  0
 13 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 22 29  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251834

   N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-1-methyl-5-nitro-3-(1-phenylethyl)-2,4-dihydropyrimidin-6-amine

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: 415.93

Molecular Weight (Monoisotopic): 415.1775

AlogP: 3.97

#Rotatable Bonds: 7

Polar Surface Area: 65.75

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.22

CX LogP: 4.08

CX LogD: 4.08

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -1.31

References

1. Sun C, Jin J, Zhu J, Wang H, Yang D, Xing J..  (2010)  Discovery of bis-aromatic ring neonicotinoid analogues fixed as cis-configuration: Synthesis, insecticidal activities, and molecular docking studies.,  20  (11): [PMID:20452211] [10.1016/j.bmcl.2010.04.050]

Source

Source(1):

• Scientific Literature