US8853193, 19-1

ID: ALA3698941

PubChem CID: 58413248

Max Phase: Preclinical

Molecular Formula: C20H22FN5O4S

Molecular Weight: 447.49

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H22FN5O4S/c1-10-16-18(24-9-25-19(16)31-17(10)20(28)29-3)26-14-5-4-12(21)6-15(14)30-13(7-22)8-23-11(2)27/h4-6,9,13H,7-8,22H2,1-3H3,(H,23,27)(H,24,25,26)

Standard InChI Key:  RBYNIYZLGVBSMK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    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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   -3.8939    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
   -7.8098   -2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8513   -3.5773    0.0000 N   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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8325   -7.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8747   -8.0763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7964   -8.0868    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
 22 23  1  0
 21 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:

   

   ALA3698941

   Methyl 4-[2-(1-acetamido-3-aminopropan-2-yl)oxy-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: 447.49

Molecular Weight (Monoisotopic): 447.1377

AlogP: 2.51

#Rotatable Bonds: 8

Polar Surface Area: 128.46

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.88

CX LogP: 2.25

CX LogD: 0.77

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: -1.51

References

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

Source

Source(1):

• BindingDB Database