2-(3-Trifluoromethylanilino)-5H-benzothiopyrano[4,3-d]pyrimidine

ID: ALA4250974

PubChem CID: 145984596

Max Phase: Preclinical

Molecular Formula: C18H12F3N3S

Molecular Weight: 359.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  FC(F)(F)c1cccc(Nc2ncc3c(n2)-c2ccccc2SC3)c1

Standard InChI:  InChI=1S/C18H12F3N3S/c19-18(20,21)12-4-3-5-13(8-12)23-17-22-9-11-10-25-15-7-2-1-6-14(15)16(11)24-17/h1-9H,10H2,(H,22,23,24)

Standard InChI Key:  VCXNKIFBNKFJEG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    2.3428  -12.9884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417  -13.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0497  -14.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0480  -12.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7566  -12.9848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7554  -13.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4616  -14.2144    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1735  -13.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4639  -12.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1737  -12.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8857  -12.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8893  -11.7591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1749  -11.3461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4657  -11.7555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1752  -10.5289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8830  -10.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5888  -10.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2962  -10.1257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2969   -9.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5843   -8.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8799   -9.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0061  -10.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6498  -10.9075    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0239  -11.3489    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.8046  -10.2324    0.0000 F   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
 22 23  1  0
 22 24  1  0
 22 25  1  0
 18 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4250974

   ---

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: 359.38

Molecular Weight (Monoisotopic): 359.0704

AlogP: 5.51

#Rotatable Bonds: 2

Polar Surface Area: 37.81

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.87

CX Basic pKa: 1.60

CX LogP: 5.36

CX LogD: 5.36

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.65

Np Likeness Score: -1.59

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