(R)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)prop-2-en-1-one

ID: ALA5287545

Max Phase: Preclinical

Molecular Formula: C22H22N6O3

Molecular Weight: 418.46

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CC[C@@H](n2nc(C#Cc3cc(OC)cc(OC)c3)c3c(N)ncnc32)C1

Standard InChI:  InChI=1S/C22H22N6O3/c1-4-19(29)27-8-7-15(12-27)28-22-20(21(23)24-13-25-22)18(26-28)6-5-14-9-16(30-2)11-17(10-14)31-3/h4,9-11,13,15H,1,7-8,12H2,2-3H3,(H2,23,24,25)/t15-/m1/s1

Standard InChI Key:  KEIPNCCJPRMIAX-OAHLLOKOSA-N

Molfile:  

 
     RDKit          2D

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    1.9573   -3.2740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230   -3.7567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211   -4.4264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5387   -3.1243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5387   -2.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434   -2.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7301   -2.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434   -3.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7104   -1.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9948   -1.4228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2834   -1.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2834   -0.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9948    0.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7104   -0.1872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0145   -0.5990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5013   -1.2605    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5013    0.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2434    0.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0103    1.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2641    2.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849    3.0328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0353    3.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7717    3.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250    3.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0712    2.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1321    3.5445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7104    2.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5844    4.4264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916    4.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9948    1.0483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  1  4  2  0
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  6  7  1  0
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 10 11  1  0
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 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 16 17  1  0
 12 17  1  0
  7 17  1  1
 16 18  2  0
 13 18  1  0
 18 19  1  0
 19 20  3  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 25 27  1  0
 27 28  1  0
 23 29  1  0
 29 30  1  0
 14 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287545

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 418.46

Molecular Weight (Monoisotopic): 418.1753

AlogP: 1.78

#Rotatable Bonds: 4

Polar Surface Area: 108.39

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.58

CX LogP: 1.77

CX LogD: 1.77

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: -0.80

References

1. Ito S, Otsuki S, Ohsawa H, Hirano A, Kazuno H, Yamashita S, Egami K, Shibata Y, Yamamiya I, Yamashita F, Kodama Y, Funabashi K, Kazuno H, Komori T, Suzuki S, Sootome H, Hirai H, Sagara T..  (2023)  Discovery of Futibatinib: The First Covalent FGFR Kinase Inhibitor in Clinical Use.,  14  (4): [PMID:37077386] [10.1021/acsmedchemlett.3c00006]

Source

Source(1):

• Scientific Literature