4-((5-(mesityloxy)-2-nitropyridin-3-yl)amino)benzonitrile

ID: ALA4212784

PubChem CID: 145963938

Max Phase: Preclinical

Molecular Formula: C21H18N4O3

Molecular Weight: 374.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C)c(Oc2cnc([N+](=O)[O-])c(Nc3ccc(C#N)cc3)c2)c(C)c1

Standard InChI:  InChI=1S/C21H18N4O3/c1-13-8-14(2)20(15(3)9-13)28-18-10-19(21(23-12-18)25(26)27)24-17-6-4-16(11-22)5-7-17/h4-10,12,24H,1-3H3

Standard InChI Key:  CKYSDRQIAJTVDC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   12.6784   -5.4465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3901   -5.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3858   -6.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0967   -7.0876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8096   -6.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8072   -5.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0957   -5.4445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5177   -5.4385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9664   -5.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2581   -5.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5508   -5.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5502   -6.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2627   -7.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9713   -6.6715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5150   -4.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2214   -4.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2191   -3.3856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5095   -2.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7967   -3.3938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8025   -4.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5255   -7.0855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2327   -6.6720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5264   -7.9068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5072   -2.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5035   -1.3401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2596   -4.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6813   -7.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8420   -7.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  1  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  8 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  2  0
 21 23  1  0
  5 21  1  0
 24 25  3  0
 18 24  1  0
 10 26  1  0
 14 27  1  0
 12 28  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4212784

   ---

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: 374.40

Molecular Weight (Monoisotopic): 374.1379

AlogP: 5.32

#Rotatable Bonds: 5

Polar Surface Area: 101.08

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.92

CX Basic pKa: ┄

CX LogP: 6.93

CX LogD: 6.93

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.48

Np Likeness Score: -1.31

References

1. Liu Z, Tian Y, Liu J, Huang B, Kang D, De Clercq E, Daelemans D, Pannecouque C, Zhan P, Liu X..  (2017)  Design, synthesis and anti-HIV evaluation of novel diarylpyridine derivatives as potent HIV-1 NNRTIs.,  140  [PMID:28987601] [10.1016/j.ejmech.2017.07.012]

Source

Source(1):

• Scientific Literature