5-[6-(azetidin-1-yl)-2-cyclopropyl-pyrimidin-4-yl]-3-[1-(4-methylthiazol-2-yl)ethoxy]pyridin-2-amine

ID: ALA3730558

PubChem CID: 117688597

Max Phase: Preclinical

Molecular Formula: C21H24N6OS

Molecular Weight: 408.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1csc(C(C)Oc2cc(-c3cc(N4CCC4)nc(C4CC4)n3)cnc2N)n1

Standard InChI:  InChI=1S/C21H24N6OS/c1-12-11-29-21(24-12)13(2)28-17-8-15(10-23-19(17)22)16-9-18(27-6-3-7-27)26-20(25-16)14-4-5-14/h8-11,13-14H,3-7H2,1-2H3,(H2,22,23)

Standard InChI Key:  IZSWOHGDYNYOSX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    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
    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 C   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
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2978    3.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2954    5.2529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0048    6.0009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3026    5.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3002    3.7488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003   -1.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939    6.0054    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9994    5.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3830    7.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9329    7.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6035    5.9971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2783    7.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0242    5.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969    0.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5517   -0.8722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5554   -1.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8054   -3.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3382   -2.9741    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7488   -1.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  3  8  1  0
  5 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 16  1  0
 21 20  1  0
 22 21  1  0
 20 22  1  0
 12 20  1  0
 15 23  1  0
 15 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 24  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3730558

   5-[6-(Azetidin-1-yl)-2-cyclopropylpyrimidin-4-yl]-3-[1-(4-methyl-1,3-thiazol-2-yl)ethoxy]pyridin-2-amine

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: 408.53

Molecular Weight (Monoisotopic): 408.1732

AlogP: 4.11

#Rotatable Bonds: 6

Polar Surface Area: 90.05

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.70

CX LogP: 3.66

CX LogD: 3.65

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: -1.41

References

1.  (2014)  Biheteroaryl compounds and uses thereof, 

2.  (2014)  Biheteroaryl compounds and uses thereof, 

Source

Source(1):

• Patent Bioactivity Data