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

ID: ALA4238493

PubChem CID: 145985681

Max Phase: Preclinical

Molecular Formula: C20H18ClN3O3S

Molecular Weight: 415.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Nc2ncc3c(n2)-c2ccc(Cl)cc2SC3)cc(OC)c1OC

Standard InChI:  InChI=1S/C20H18ClN3O3S/c1-25-15-7-13(8-16(26-2)19(15)27-3)23-20-22-9-11-10-28-17-6-12(21)4-5-14(17)18(11)24-20/h4-9H,10H2,1-3H3,(H,22,23,24)

Standard InChI Key:  HRHJOSIEPOXSQD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   12.3184  -20.7434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3172  -21.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0253  -21.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0235  -20.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7321  -20.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7309  -21.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4371  -21.9695    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.1490  -21.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4394  -20.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1492  -20.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8613  -20.3361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8648  -19.5142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1504  -19.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4412  -19.5106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1507  -18.2839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.8585  -17.8755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5643  -18.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2717  -17.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2724  -17.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5598  -16.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8554  -17.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6092  -21.9710    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.9791  -18.2899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9797  -16.6534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9788  -15.8362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5572  -15.8369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8482  -15.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9784  -19.1071    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
 18 23  1  0
 19 24  1  0
 24 25  1  0
 20 26  1  0
 26 27  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4238493

   ---

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: 415.90

Molecular Weight (Monoisotopic): 415.0757

AlogP: 5.17

#Rotatable Bonds: 5

Polar Surface Area: 65.50

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.40

CX Basic pKa: 1.61

CX LogP: 4.61

CX LogD: 4.61

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.62

Np Likeness Score: -0.99

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