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

ID: ALA2251833

PubChem CID: 76311904

Max Phase: Preclinical

Molecular Formula: C21H26ClN5O3

Molecular Weight: 431.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(Cc1ccc(Cl)nc1)C1=C([N+](=O)[O-])CN(Cc2ccc(OC)cc2)CN1C

Standard InChI:  InChI=1S/C21H26ClN5O3/c1-4-26(13-17-7-10-20(22)23-11-17)21-19(27(28)29)14-25(15-24(21)2)12-16-5-8-18(30-3)9-6-16/h5-11H,4,12-15H2,1-3H3

Standard InChI Key:  SULXWZUYIYAMCX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    1.1996   -8.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1985   -9.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9065   -9.6934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6162   -9.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6133   -8.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9047   -8.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4904   -9.6925    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3195   -8.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0287   -8.4560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7349   -8.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4467   -8.4556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1507   -8.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1519   -7.2303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4428   -6.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7326   -7.2316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0318   -9.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3257   -9.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4473   -9.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0232   -6.8226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3160   -7.2320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0223   -6.0054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8596   -6.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5673   -7.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5624   -8.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2693   -8.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9780   -8.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9754   -7.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2679   -6.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6863   -8.4526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6873   -9.2698    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
 29 30  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2251833

   N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-3-[(4-methoxyphenyl)methyl]-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: 431.92

Molecular Weight (Monoisotopic): 431.1724

AlogP: 3.42

#Rotatable Bonds: 8

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: 3.66

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: -1.25

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