Cyclopropanesulfonic acid{4-[4-((R)-pyrrolidin-3-ylamino)-thieno[3,2-d]pyrimidin-2-yl]-pyridin-2-yl}-amide

ID: ALA3728643

PubChem CID: 89596384

Max Phase: Preclinical

Molecular Formula: C18H20N6O2S2

Molecular Weight: 416.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(Nc1cc(-c2nc(N[C@@H]3CCNC3)c3sccc3n2)ccn1)C1CC1

Standard InChI:  InChI=1S/C18H20N6O2S2/c25-28(26,13-1-2-13)24-15-9-11(3-7-20-15)17-22-14-5-8-27-16(14)18(23-17)21-12-4-6-19-10-12/h3,5,7-9,12-13,19H,1-2,4,6,10H2,(H,20,24)(H,21,22,23)/t12-/m1/s1

Standard InChI Key:  JBYHAFIQCAXEEH-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

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   -3.6222    5.9944    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6215    4.7944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971   -3.0138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935   -3.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4279   -5.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8944   -5.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6474   -4.2692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6464   -3.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168    1.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9144    0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2151    1.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2185    2.9892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9211    3.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6204    2.9950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9214    5.2429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6225    7.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3727    8.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8727    8.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  8  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  9  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
  7 13  1  0
 14 13  1  6
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
  5 19  1  0
 23 25  1  0
 25  2  1  0
  2 26  1  0
 27 26  1  0
 28 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3728643

   N-[4-[4-[[(3R)-pyrrolidin-3-yl]amino]thieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]cyclopropanesulfonamide

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: 416.53

Molecular Weight (Monoisotopic): 416.1089

AlogP: 2.43

#Rotatable Bonds: 6

Polar Surface Area: 108.90

Molecular Species: BASE

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.60

CX Basic pKa: 10.31

CX LogP: 0.68

CX LogD: 0.28

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: -1.74

References

1.  (2013)  Thienopyrimidine inhibitors of atypical protein kinase C, 

Source

Source(1):

• Patent Bioactivity Data