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

ID: ALA2251831

PubChem CID: 46221101

Max Phase: Preclinical

Molecular Formula: C20H24ClN5O2

Molecular Weight: 401.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(Cc1ccc(Cl)nc1)C1=C([N+](=O)[O-])CN(Cc2ccccc2)CN1C

Standard InChI:  InChI=1S/C20H24ClN5O2/c1-3-25(13-17-9-10-19(21)22-11-17)20-18(26(27)28)14-24(15-23(20)2)12-16-7-5-4-6-8-16/h4-11H,3,12-15H2,1-2H3

Standard InChI Key:  KZJPFBNZPNKRBS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   24.4607   -3.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4595   -4.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1676   -4.5261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8772   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8744   -3.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1658   -2.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7515   -4.5252    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.5806   -2.8828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2898   -3.2887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9960   -2.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7077   -3.2883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4118   -2.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4129   -2.0630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7038   -1.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9936   -2.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2929   -4.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5867   -4.5171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7083   -4.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2843   -1.6553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5770   -2.0647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2834   -0.8381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1207   -1.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8284   -2.0630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8235   -2.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5304   -3.2863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2391   -2.8776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2365   -2.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5290   -1.6514    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
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251831

   3-benzyl-N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-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: 401.90

Molecular Weight (Monoisotopic): 401.1619

AlogP: 3.41

#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: 3.98

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: -1.34

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