8-Methoxy-2-(3,4,5-trimethoxyanilino)-5H-benzothiopyrano[4,3-d]pyrimidine

ID: ALA4248316

PubChem CID: 145982636

Max Phase: Preclinical

Molecular Formula: C21H21N3O4S

Molecular Weight: 411.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)SCc1cnc(Nc3cc(OC)c(OC)c(OC)c3)nc1-2

Standard InChI:  InChI=1S/C21H21N3O4S/c1-25-14-5-6-15-18(9-14)29-11-12-10-22-21(24-19(12)15)23-13-7-16(26-2)20(28-4)17(8-13)27-3/h5-10H,11H2,1-4H3,(H,22,23,24)

Standard InChI Key:  NWKGWZQDSLNWBX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   12.8755   -4.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8744   -5.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5824   -6.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5806   -4.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2893   -4.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2881   -5.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9943   -6.1044    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.7062   -5.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9966   -4.4632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7063   -4.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4184   -4.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4220   -3.6491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7076   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9984   -3.6455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7078   -2.4189    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.4157   -2.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1215   -2.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8289   -2.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8296   -1.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1170   -0.7890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4126   -1.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1664   -6.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4590   -5.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5362   -2.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5356   -3.2421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5368   -0.7883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2450   -1.1962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1144    0.0296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4053    0.4345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  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
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  2 22  1  0
 22 23  1  0
 18 24  1  0
 24 25  1  0
 19 26  1  0
 26 27  1  0
 20 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4248316

   ---

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: 411.48

Molecular Weight (Monoisotopic): 411.1253

AlogP: 4.53

#Rotatable Bonds: 6

Polar Surface Area: 74.73

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.41

CX Basic pKa: 1.72

CX LogP: 3.85

CX LogD: 3.85

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.63

Np Likeness Score: -0.80

References

1. Salerno S, García-Argáez AN, Barresi E, Taliani S, Simorini F, La Motta C, Amendola G, Tomassi S, Cosconati S, Novellino E, Da Settimo F, Marini AM, Via LD..  (2018)  New insights in the structure-activity relationships of 2-phenylamino-substituted benzothiopyrano[4,3-d]pyrimidines as kinase inhibitors.,  150  [PMID:29547832] [10.1016/j.ejmech.2018.03.013]

Source

Source(1):

• Scientific Literature