N-(2-((2-aminoethyl)(ethyl)amino)-5-(3-cyano-7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-ylamino)phenyl)acetamide

ID: ALA3808860

PubChem CID: 127045537

Max Phase: Preclinical

Molecular Formula: C22H27N9O

Molecular Weight: 433.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CCN)c1ccc(Nc2cc(NC3CC3)n3ncc(C#N)c3n2)cc1NC(C)=O

Standard InChI:  InChI=1S/C22H27N9O/c1-3-30(9-8-23)19-7-6-17(10-18(19)26-14(2)32)27-20-11-21(28-16-4-5-16)31-22(29-20)15(12-24)13-25-31/h6-7,10-11,13,16,28H,3-5,8-9,23H2,1-2H3,(H,26,32)(H,27,29)

Standard InChI Key:  YKCZPJDTUBPIML-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -4.8647   -3.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8327   -3.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8500   -4.9736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1731   -3.0384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1914   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4980   -0.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5133    0.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2219    1.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9153    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9001   -0.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6217    1.4865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971   -3.0138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2935   -3.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9615   -5.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7145   -3.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1783    2.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5503    3.7690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7916   -1.5619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7821   -3.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8171   -3.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0979   -0.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3915   -1.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4360   -0.9929    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  5 10  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 17  1  0
 18 19  2  0
 19 20  1  0
 17 18  1  0
 12 20  2  0
 22 23  1  0
 23 24  1  0
 22 24  1  0
 21 22  1  0
 16 21  1  0
 25 26  3  0
 20 25  1  0
 11 14  1  0
  9 11  1  0
 28 29  1  0
 27 28  1  0
 30 31  1  0
 31 32  1  0
 27 30  1  0
  6 27  1  0
  4  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3808860

   ---

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: 433.52

Molecular Weight (Monoisotopic): 433.2339

AlogP: 2.66

#Rotatable Bonds: 9

Polar Surface Area: 136.40

Molecular Species: BASE

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.84

CX Basic pKa: 9.61

CX LogP: 1.48

CX LogD: -0.67

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -1.92

References

1. Dowling JE, Alimzhanov M, Bao L, Chuaqui C, Denz CR, Jenkins E, Larsen NA, Lyne PD, Pontz T, Ye Q, Holdgate GA, Snow L, O'Connell N, Ferguson AD..  (2016)  Potent and Selective CK2 Kinase Inhibitors with Effects on Wnt Pathway Signaling in Vivo.,  7  (3): [PMID:26985319] [10.1021/acsmedchemlett.5b00452]

Source

Source(1):

• Scientific Literature