6-methoxy-5-((2-(2-nitrophenyl)ethylidene)amino)-N4-phenylpyrimidine-2,4-diamine

ID: ALA5286699

Max Phase: Preclinical

Molecular Formula: C19H18N6O3

Molecular Weight: 378.39

Names and Identifiers

Canonical SMILES:  COc1nc(N)nc(Nc2ccccc2)c1/N=C/Cc1ccccc1[N+](=O)[O-]

Standard InChI:  InChI=1S/C19H18N6O3/c1-28-18-16(21-12-11-13-7-5-6-10-15(13)25(26)27)17(23-19(20)24-18)22-14-8-3-2-4-9-14/h2-10,12H,11H2,1H3,(H3,20,22,23,24)/b21-12+

Standard InChI Key:  NHTIBVCQAJAWAI-CIAFOILYSA-N

Molfile:  

 
     RDKit          2D

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   -1.7852    0.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7835   -1.0306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998   -0.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7852    1.4435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    1.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2145   -1.0350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587   -1.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587    0.6190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0704    0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851    0.2064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120    0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120   -0.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5017   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851   -0.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4998    1.4440    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    1.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7852    1.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731   -2.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731   -3.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587   -3.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557   -3.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557   -2.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  2  7  1  0
  7  8  1  0
  6  9  1  0
  4 10  1  0
 10 11  1  0
  3 12  1  0
 12 13  2  0
 13 14  1  0
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 18 17  2  0
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 20 19  2  0
 15 20  1  0
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 21 22  1  0
 21 23  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 11 24  2  0
 28 11  1  0
M  CHG  2  21   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA5286699

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 378.39

Molecular Weight (Monoisotopic): 378.1440

AlogP: 3.66

#Rotatable Bonds: 7

Polar Surface Area: 128.56

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.11

CX Basic pKa: 5.90

CX LogP: 3.95

CX LogD: 3.94

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.36

Np Likeness Score: -0.99

References

1. Rojas S, Parravicini O, Vettorazzi M, Tosso R, Garro A, Gutiérrez L, Andújar S, Enriz R..  (2020)  Combined MD/QTAIM techniques to evaluate ligand-receptor interactions. Scope and limitations.,  208  [PMID:32949964] [10.1016/j.ejmech.2020.112792]

Source

Source(1):

• Scientific Literature