N-[6-[4-(2-Amino-2-oxoethyl)piperazin-1-yl]-2,2-dimethyl-3H-benzofuran-5-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

ID: ALA4483551

PubChem CID: 129284078

Max Phase: Preclinical

Molecular Formula: C23H27N7O3

Molecular Weight: 449.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1(C)Cc2cc(NC(=O)c3cnn4cccnc34)c(N3CCN(CC(N)=O)CC3)cc2O1

Standard InChI:  InChI=1S/C23H27N7O3/c1-23(2)12-15-10-17(27-22(32)16-13-26-30-5-3-4-25-21(16)30)18(11-19(15)33-23)29-8-6-28(7-9-29)14-20(24)31/h3-5,10-11,13H,6-9,12,14H2,1-2H3,(H2,24,31)(H,27,32)

Standard InChI Key:  TVWUXEGJFJCUJM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    1.7458  -11.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4557  -11.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7505  -10.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4287  -12.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1370  -11.7323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1323  -10.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4231  -10.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8375  -10.4972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8463  -12.1381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8325   -9.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5377   -9.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1223   -9.2758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4169   -8.2775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6187   -8.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8298   -8.9827    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2886   -9.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5445  -10.3608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3413  -10.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8817   -9.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6229   -9.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7222  -11.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7189  -10.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9382  -10.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9435  -11.9942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8452  -12.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5504  -13.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2589  -12.9497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2577  -12.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5480  -11.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667  -13.3582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6743  -12.9496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3821  -13.3581    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6743  -12.1324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
 21  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7 22  1  0
  6  8  1  0
  5  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 11 16  2  0
 15 13  1  0
 13 14  2  0
 14 11  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  2  0
 22 23  1  0
 23  2  1  0
  2 24  1  0
 24 21  1  0
  9 25  1  0
  9 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483551

   ---

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: 449.52

Molecular Weight (Monoisotopic): 449.2175

AlogP: 1.30

#Rotatable Bonds: 5

Polar Surface Area: 118.09

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.78

CX Basic pKa: 6.00

CX LogP: 0.95

CX LogD: 0.93

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.60

Np Likeness Score: -1.63

References

1. Bryan MC, Drobnick J, Gobbi A, Kolesnikov A, Chen Y, Rajapaksa N, Ndubaku C, Feng J, Chang W, Francis R, Yu C, Choo EF, DeMent K, Ran Y, An L, Emson C, Huang Z, Sujatha-Bhaskar S, Brightbill H, DiPasquale A, Maher J, Wai J, McKenzie BS, Lupardus PJ, Zarrin AA, Kiefer JR..  (2019)  Development of Potent and Selective Pyrazolopyrimidine IRAK4 Inhibitors.,  62  (13): [PMID:31082230] [10.1021/acs.jmedchem.9b00439]

Source

Source(1):

• Scientific Literature