N-(2-(4-(aminomethyl)piperidin-1-yl)-5-chlorophenyl)-6-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxamide

ID: ALA3353219

PubChem CID: 58056241

Product Number: N608905, Order Now?

Max Phase: Preclinical

Molecular Formula: C19H21ClN6O2

Molecular Weight: 400.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCC1CCN(c2ccc(Cl)cc2NC(=O)c2cnn3cc(O)cnc23)CC1

Standard InChI:  InChI=1S/C19H21ClN6O2/c20-13-1-2-17(25-5-3-12(8-21)4-6-25)16(7-13)24-19(28)15-10-23-26-11-14(27)9-22-18(15)26/h1-2,7,9-12,27H,3-6,8,21H2,(H,24,28)

Standard InChI Key:  BNVZRFQNZWYPQH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.4730  -10.4538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1058   -9.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6390   -8.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780   -7.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7113   -7.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7055   -8.3648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1667   -9.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6333  -10.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7624   -8.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7662   -9.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2334   -8.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6967   -7.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8704   -7.1786    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6928   -6.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2256   -6.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2234   -5.5086    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6890   -4.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8631   -3.8341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -2.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8032   -3.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    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
    0.0000    2.7000    0.0000 O   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 N   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  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  3  1  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15  9  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 19  2  0
 28 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3353219

   N-{2-[4-(aminomethyl)piperidin-1-yl]-5-chlorophenyl}-6-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxamide

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: 400.87

Molecular Weight (Monoisotopic): 400.1415

AlogP: 2.52

#Rotatable Bonds: 4

Polar Surface Area: 108.78

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.21

CX Basic pKa: 10.22

CX LogP: 1.46

CX LogD: 1.28

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.62

Np Likeness Score: -1.84

References

1. Chaudhary D, Robinson S, Romero DL..  (2015)  Recent advances in the discovery of small molecule inhibitors of interleukin-1 receptor-associated kinase 4 (IRAK4) as a therapeutic target for inflammation and oncology disorders.,  58  (1): [PMID:25479567] [10.1021/jm5016044]

2.  (2016)  Pyrazolo[1,5a]pyrimidine derivatives as IRAK4 modulators, 

Source

Source(2):

• Scientific Literature
• BindingDB Database