US8853193, 13-2

ID: ALA3698932

PubChem CID: 58413310

Max Phase: Preclinical

Molecular Formula: C21H23FN4O4S

Molecular Weight: 446.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1sc2ncnc(Nc3ccc(F)cc3OC(C)CCNC(C)=O)c2c1C

Standard InChI:  InChI=1S/C21H23FN4O4S/c1-11(7-8-23-13(3)27)30-16-9-14(22)5-6-15(16)26-19-17-12(2)18(21(28)29-4)31-20(17)25-10-24-19/h5-6,9-11H,7-8H2,1-4H3,(H,23,27)(H,24,25,26)

Standard InChI Key:  PLEXKFLHWRNFAD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    4.6580   -5.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0559   -4.4171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -4.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9569   -5.4595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8939    0.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1904    1.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4920    0.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5291    1.3671    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4971   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2007   -1.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2090   -2.9918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5125   -3.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5485   -3.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5208   -5.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8242   -5.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8325   -7.4814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1359   -8.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1426   -9.4254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1720   -7.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4916   -3.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 13  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 11 29  2  0
 29  7  1  0
 29 30  1  0
 30  5  2  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3698932

   Methyl 4-[2-(4-acetamidobutan-2-yloxy)-4-fluoroanilino]-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

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: 446.50

Molecular Weight (Monoisotopic): 446.1424

AlogP: 3.96

#Rotatable Bonds: 8

Polar Surface Area: 102.44

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.96

CX LogP: 3.46

CX LogD: 3.46

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.50

Np Likeness Score: -1.79

References

1.  (2014)  Thienopyrimidines containing a substituted alkyl group for pharmaceutical compositions, 

Source

Source(1):

• BindingDB Database