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

ID: ALA2251832

PubChem CID: 76322793

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(Cc2ccc(C)cc2)CN1C

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

Standard InChI Key:  UCGNFVGRVMODFR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   32.3065   -3.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3054   -4.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0134   -4.9017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7231   -4.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7203   -3.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0116   -3.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5974   -4.9008    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   34.4264   -3.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1357   -3.6643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.8418   -3.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5536   -3.6639    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2577   -3.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2588   -2.4386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5497   -2.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8395   -2.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1387   -4.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4326   -4.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5542   -4.4811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1302   -2.0309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4229   -2.4403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.1292   -1.2137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.9665   -2.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6742   -2.4386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6694   -3.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3762   -3.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0849   -3.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0823   -2.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3749   -2.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7932   -3.6609    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
 26 29  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251832

   N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-1-methyl-3-[(4-methylphenyl)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: 415.93

Molecular Weight (Monoisotopic): 415.1775

AlogP: 3.72

#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: 3.97

CX LogP: 4.18

CX LogD: 4.18

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.39

Np Likeness Score: -1.38

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