(R)-1-{4-[4-((R)-Pyrrolidin-3-ylamino)-thieno[3,2-d]pyrimidin-2-yl]-pyridin-2-ylamino}-propan-2-ol

ID: ALA3731352

PubChem CID: 89596368

Max Phase: Preclinical

Molecular Formula: C18H22N6OS

Molecular Weight: 370.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](O)CNc1cc(-c2nc(N[C@@H]3CCNC3)c3sccc3n2)ccn1

Standard InChI:  InChI=1S/C18H22N6OS/c1-11(25)9-21-15-8-12(2-6-20-15)17-23-14-4-7-26-16(14)18(24-17)22-13-3-5-19-10-13/h2,4,6-8,11,13,19,25H,3,5,9-10H2,1H3,(H,20,21)(H,22,23,24)/t11-,13-/m1/s1

Standard InChI Key:  HDAPHVRPLCQEFJ-DGCLKSJQSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -1.0028   -1.5132    0.0000 N   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
    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 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
   -2.3155   -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
   -6.2151   -1.4892    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
   -4.9144   -0.7421    0.0000 C   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
   -2.2935    3.7700    0.0000 C   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
   -6.2185   -2.9892    0.0000 N   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
   -3.6168   -1.4950    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
   -4.9214   -5.2429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6222   -5.9944    0.0000 C   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
   -4.6620   -8.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5838   -8.0961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  6 14  2  0
  5  4  1  0
  8 16  1  0
  4  3  2  0
 17 11  2  0
  3  8  1  0
 15 12  1  0
 16  5  2  0
 14  2  1  0
  1  7  2  0
 12 10  2  0
 13  2  1  1
 10 17  1  0
  9 15  2  0
 14  3  1  0
 11  9  1  0
  7 17  1  0
  7  6  1  0
 13 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 13  1  0
 12 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3731352

   (2R)-1-[[4-[4-[[(3R)-pyrrolidin-3-yl]amino]thieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]amino]propan-2-ol

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: 370.48

Molecular Weight (Monoisotopic): 370.1576

AlogP: 2.32

#Rotatable Bonds: 6

Polar Surface Area: 94.99

Molecular Species: BASE

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.31

CX LogP: 2.05

CX LogD: -0.73

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.53

Np Likeness Score: -1.31

References

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

Source

Source(1):

• Patent Bioactivity Data