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

ID: ALA2251830

PubChem CID: 76319129

Max Phase: Preclinical

Molecular Formula: C20H24ClN5O3

Molecular Weight: 417.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(Cc1ccc(Cl)nc1)C1=C([N+](=O)[O-])CN(c2ccccc2OC)CN1C

Standard InChI:  InChI=1S/C20H24ClN5O3/c1-4-24(12-15-9-10-19(21)22-11-15)20-17(26(27)28)13-25(14-23(20)2)16-7-5-6-8-18(16)29-3/h5-11H,4,12-14H2,1-3H3

Standard InChI Key:  WICLXCHNTMUVAR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   15.8678   -3.3678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8666   -4.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5747   -4.5963    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2843   -4.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2815   -3.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5729   -2.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1586   -4.5954    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.9877   -2.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6969   -3.3588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4031   -2.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1148   -3.3585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8189   -2.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8200   -2.1331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1110   -1.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4007   -2.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7000   -4.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9938   -4.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1154   -4.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6914   -1.7254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9841   -2.1348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6905   -0.9083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5278   -1.7246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2355   -2.1365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9427   -1.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9432   -0.9105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2305   -0.5021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5262   -0.9124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2339   -2.9537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9407   -3.3637    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  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 23 28  1  0
 28 29  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251830

   N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-3-(2-methoxyphenyl)-1-methyl-5-nitro-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: 417.90

Molecular Weight (Monoisotopic): 417.1568

AlogP: 3.42

#Rotatable Bonds: 7

Polar Surface Area: 74.98

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.85

CX LogP: 3.67

CX LogD: 3.67

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -1.26

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