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

ID: ALA2251835

PubChem CID: 76315448

Max Phase: Preclinical

Molecular Formula: C22H28ClN5O2

Molecular Weight: 429.95

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H28ClN5O2/c1-5-26(13-18-8-11-21(23)24-12-18)22-20(28(29)30)14-27(15-25(22)4)17(3)19-9-6-16(2)7-10-19/h6-12,17H,5,13-15H2,1-4H3

Standard InChI Key:  ZILJKJBKNFAREJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   19.7318   -8.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7307   -9.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4455   -9.7568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1620   -9.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1591   -8.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4437   -8.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0160   -9.7559    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.8720   -8.0978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5881   -8.5076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3009   -8.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0195   -8.5072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7303   -8.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7314   -7.2702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0156   -6.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2986   -7.2715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5912   -9.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8782   -9.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0201   -9.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5825   -6.8586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8685   -7.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5815   -6.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4459   -6.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1604   -7.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1555   -8.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8692   -8.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5845   -8.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5819   -7.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8678   -6.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4459   -6.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2996   -8.5042    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
 26 30  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251835

   N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-1-methyl-3-[1-(4-methylphenyl)ethyl]-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: 429.95

Molecular Weight (Monoisotopic): 429.1932

AlogP: 4.28

#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: 4.20

CX LogP: 4.59

CX LogD: 4.59

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.37

Np Likeness Score: -1.35

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