rac-2-Amino-3-cyano-4-p-nitrophenyl-6-(2-pyridyl)-5-phenylsulfinyl-4H-pyran

ID: ALA4218932

PubChem CID: 145967803

Max Phase: Preclinical

Molecular Formula: C23H16N4O4S

Molecular Weight: 444.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CC1=C(N)OC(c2ccccn2)=C([S+]([O-])c2ccccc2)C1c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C23H16N4O4S/c24-14-18-20(15-9-11-16(12-10-15)27(28)29)22(32(30)17-6-2-1-3-7-17)21(31-23(18)25)19-8-4-5-13-26-19/h1-13,20H,25H2

Standard InChI Key:  JVMPAJWNHNSYPQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   19.7715  -13.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7715  -13.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4841  -14.2533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1967  -13.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1967  -13.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4841  -12.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0552  -12.6096    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.3414  -13.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4841  -11.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2012  -11.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2015  -10.5450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4859  -10.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7686  -10.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7717  -11.3715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9097  -12.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6218  -12.2004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6256  -12.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9165  -13.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9185  -13.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6355  -14.2607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3460  -13.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9111  -14.2585    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0527  -11.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3527  -14.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5263  -14.5528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1117  -15.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5185  -15.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3481  -15.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7630  -15.2728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4853   -9.3031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7697   -8.8936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1998   -8.8918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  7  1  0
  7  8  1  0
  6  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
 15 16  3  0
  5 15  1  0
  8 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  8  1  0
  4 22  1  0
  7 23  1  0
  2 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 30 31  2  0
 30 32  1  0
 12 30  1  0
M  CHG  4   7   1  23  -1  30   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4218932

   ---

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: 444.47

Molecular Weight (Monoisotopic): 444.0892

AlogP: 3.97

#Rotatable Bonds: 5

Polar Surface Area: 138.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.82

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.36

Np Likeness Score: -1.05

References

1. Recio R, Vengut-Climent E, Mouillac B, Orcel H, López-Lázaro M, Calderón-Montaño JM, Álvarez E, Khiar N, Fernández I..  (2017)  Design, synthesis and biological studies of a library of NK1-Receptor Ligands Based on a 5-arylthiosubstituted 2-amino-4,6-diaryl-3-cyano-4H-pyran core: Switch from antagonist to agonist effect by chemical modification.,  138  [PMID:28710964] [10.1016/j.ejmech.2017.06.056]

Source

Source(1):

• Scientific Literature