N-(3-(((5-chloro-2-((1-(2-hydroxyethyl)-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)amino)methyl)phenyl)acrylamide

ID: ALA3601120

PubChem CID: 118475644

Max Phase: Preclinical

Molecular Formula: C19H20ClN7O2

Molecular Weight: 413.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cccc(CNc2nc(Nc3cnn(CCO)c3)ncc2Cl)c1

Standard InChI:  InChI=1S/C19H20ClN7O2/c1-2-17(29)24-14-5-3-4-13(8-14)9-21-18-16(20)11-22-19(26-18)25-15-10-23-27(12-15)6-7-28/h2-5,8,10-12,28H,1,6-7,9H2,(H,24,29)(H2,21,22,25,26)

Standard InChI Key:  ALSJOMXUZWBKMB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  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
   -2.5973    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
    2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056    3.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371    5.2929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    5.2877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786    3.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497    6.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5421    6.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528    7.2976    0.0000 O   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
  4  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  2  0
 22  8  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 22  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3601120

   N-[3-[[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]methyl]phenyl]prop-2-enamide

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: 413.87

Molecular Weight (Monoisotopic): 413.1367

AlogP: 2.80

#Rotatable Bonds: 9

Polar Surface Area: 116.99

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.88

CX Basic pKa: 2.71

CX LogP: 2.30

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: -1.77

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