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

ID: ALA2251829

PubChem CID: 76315447

Max Phase: Preclinical

Molecular Formula: C19H21ClFN5O2

Molecular Weight: 405.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(Cc1ccc(Cl)nc1)C1=C([N+](=O)[O-])CN(c2ccc(F)cc2)CN1C

Standard InChI:  InChI=1S/C19H21ClFN5O2/c1-3-24(11-14-4-9-18(20)22-10-14)19-17(26(27)28)12-25(13-23(19)2)16-7-5-15(21)6-8-16/h4-10H,3,11-13H2,1-2H3

Standard InChI Key:  YWIOZUWVHOKKGP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    9.0001   -3.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9989   -4.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7070   -4.7820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4166   -4.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4138   -3.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7052   -3.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2909   -4.7811    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.1200   -3.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8292   -3.5446    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5354   -3.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2471   -3.5442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9512   -3.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9523   -2.3189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2432   -1.9108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5330   -2.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8323   -4.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1261   -4.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2477   -4.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8237   -1.9112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1164   -2.3206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8228   -1.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6601   -1.9103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3678   -2.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0750   -1.9143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0755   -1.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3628   -0.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6585   -1.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7826   -0.6867    0.0000 F   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
 25 28  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251829

   N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-3-(4-fluorophenyl)-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: 405.86

Molecular Weight (Monoisotopic): 405.1368

AlogP: 3.55

#Rotatable Bonds: 6

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: 2.85

CX LogP: 3.97

CX LogD: 3.97

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.42

Np Likeness Score: -1.61

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