5-(((1-Acryloylpyrrolidin-3-yl)methyl)amino)-7-((3,5-dimethoxyphenyl)amino)imidazo[1,2-c]pyrimidine-8-carboxamide

ID: ALA4865278

PubChem CID: 164618797

Max Phase: Preclinical

Molecular Formula: C23H27N7O4

Molecular Weight: 465.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CCC(CNc2nc(Nc3cc(OC)cc(OC)c3)c(C(N)=O)c3nccn23)C1

Standard InChI:  InChI=1S/C23H27N7O4/c1-4-18(31)29-7-5-14(13-29)12-26-23-28-21(19(20(24)32)22-25-6-8-30(22)23)27-15-9-16(33-2)11-17(10-15)34-3/h4,6,8-11,14,27H,1,5,7,12-13H2,2-3H3,(H2,24,32)(H,26,28)

Standard InChI Key:  KVAVHJDVINYPAH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   27.2009  -14.4805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0259  -14.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4360  -15.1991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4407  -13.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2658  -13.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0378  -11.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0378  -12.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7498  -12.9668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4619  -12.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7498  -11.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4589  -11.7317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0726  -11.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7429  -10.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9255  -10.5144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1766  -12.9708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1769  -13.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8916  -14.2080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3221  -11.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3197  -10.4981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6089  -11.7377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3239  -12.9721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3251  -13.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6100  -14.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6108  -15.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3264  -15.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0426  -15.0270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0383  -14.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7591  -15.4359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7633  -16.2609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8967  -15.4458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8975  -16.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9816  -15.0239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7887  -15.1952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6485  -13.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  6  7  2  0
  6 10  1  0
  7  8  1  0
  8  9  2  0
  9 11  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  2  0
  9 15  1  0
 15 16  1  0
 16 17  1  0
  6 18  1  0
 18 19  1  0
 18 20  2  0
  7 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 26 28  1  0
 28 29  1  0
 24 30  1  0
 30 31  1  0
 17 32  1  0
 32 33  1  0
 33  1  1  0
  1 34  1  0
 34 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4865278

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 465.51

Molecular Weight (Monoisotopic): 465.2125

AlogP: 2.04

#Rotatable Bonds: 9

Polar Surface Area: 136.11

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.72

CX Basic pKa: 5.13

CX LogP: 1.66

CX LogD: 1.65

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.41

Np Likeness Score: -0.99

References

1. Rao D, Li H, Ren X, Sun Y, Wen C, Zheng M, Huang H, Tang W, Xu S..  (2021)  Discovery of a potent, selective, and covalent ZAP-70 kinase inhibitor.,  219  [PMID:33845236] [10.1016/j.ejmech.2021.113393]

Source

Source(1):

• Scientific Literature