Thiophene-2-carboxylic acid{4-[4-((R)-1-methyl-pyrrolidin-3-ylamino)-thieno[3,2-d]pyrimidin-2-yl]-pyridin-2-yl}-amide

ID: ALA3733148

PubChem CID: 89596273

Max Phase: Preclinical

Molecular Formula: C21H20N6OS2

Molecular Weight: 436.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CC[C@@H](Nc2nc(-c3ccnc(NC(=O)c4cccs4)c3)nc3ccsc23)C1

Standard InChI:  InChI=1S/C21H20N6OS2/c1-27-8-5-14(12-27)23-20-18-15(6-10-30-18)24-19(26-20)13-4-7-22-17(11-13)25-21(28)16-3-2-9-29-16/h2-4,6-7,9-11,14H,5,8,12H2,1H3,(H,22,25,28)(H,23,24,26)/t14-/m1/s1

Standard InChI Key:  WBMQPMNJVTUYLP-CQSZACIVSA-N

Molfile:  

     RDKit          2D

 30 34  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
   -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
   -3.6222    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
   -2.5827    5.3949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4109    8.3577    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8776    9.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3776    9.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8380    8.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8412   -4.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  1  0
 11 10  1  6
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  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
  2 16  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 24  2  0
 14 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3733148

   N-[4-[4-[[(3R)-1-methylpyrrolidin-3-yl]amino]thieno[3,2-d]pyrimidin-2-yl]pyridin-2-yl]thiophene-2-carboxamide

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: 436.57

Molecular Weight (Monoisotopic): 436.1140

AlogP: 4.18

#Rotatable Bonds: 5

Polar Surface Area: 83.04

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.46

CX Basic pKa: 8.42

CX LogP: 4.15

CX LogD: 3.10

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: -2.26

References

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

Source

Source(1):

• Patent Bioactivity Data