N-(3-(((5-chloro-2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)methyl)phenyl)acrylamide

ID: ALA3601223

Cas Number: 1805787-93-2

PubChem CID: 92042864

Product Number: J647018, Order Now?

Max Phase: Preclinical

Molecular Formula: C26H30ClN7O2

Molecular Weight: 508.03

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cccc(CNc2nc(Nc3ccc(N4CCN(C)CC4)cc3OC)ncc2Cl)c1

Standard InChI:  InChI=1S/C26H30ClN7O2/c1-4-24(35)30-19-7-5-6-18(14-19)16-28-25-21(27)17-29-26(32-25)31-22-9-8-20(15-23(22)36-3)34-12-10-33(2)11-13-34/h4-9,14-15,17H,1,10-13,16H2,2-3H3,(H,30,35)(H2,28,29,31,32)

Standard InChI Key:  UGXCBYVBIJACEK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 39  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 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
   -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
   -2.3383   -1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8934    5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1924    6.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4915    5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4915    3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    3.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7897    3.0040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7876    1.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0858    0.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7474    0.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0842   -0.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2934    3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2883    5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847    6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863    5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8915    3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5795    7.5047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2791    8.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2762    9.7524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5739   10.5049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743    9.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8771    8.2573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5716   11.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1954    3.0153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2317    3.6204    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
  5  7  1  0
  2  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  2  0
  9 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27  9  1  0
 25 28  1  0
 28 29  1  0
 28 33  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 31 34  1  0
 27 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3601223

   JAK3-IN-1

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: 508.03

Molecular Weight (Monoisotopic): 507.2150

AlogP: 4.37

#Rotatable Bonds: 9

Polar Surface Area: 94.65

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.84

CX LogP: 4.36

CX LogD: 3.78

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.37

Np Likeness Score: -1.53

References

1. Tan L, Akahane K, McNally R, Reyskens KM, Ficarro SB, Liu S, Herter-Sprie GS, Koyama S, Pattison MJ, Labella K, Johannessen L, Akbay EA, Wong KK, Frank DA, Marto JA, Look TA, Arthur JS, Eck MJ, Gray NS..  (2015)  Development of Selective Covalent Janus Kinase 3 Inhibitors.,  58  (16): [PMID:26258521] [10.1021/acs.jmedchem.5b00710]

Source

Source(1):

• Scientific Literature