(Z)-3(1),5-dimethyl-6-oxo-1(3)-(trifluoromethyl)-1(1)H,2(1)H,3(1)H-5-aza-2(3,5)-pyrrolo[2,3-b]pyridina-1(4,1),3(4,3)-dipyrazolacyclononaphane-3(5)-carbonitrile

ID: ALA5093741

PubChem CID: 166633407

Max Phase: Preclinical

Molecular Formula: C22H19F3N8O

Molecular Weight: 468.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1Cc2nn(C)c(C#N)c2-c2cnc3[nH]cc(c3c2)-c2cn(nc2C(F)(F)F)CCCC1=O

Standard InChI:  InChI=1S/C22H19F3N8O/c1-31-11-16-19(17(7-26)32(2)29-16)12-6-13-14(9-28-21(13)27-8-12)15-10-33(5-3-4-18(31)34)30-20(15)22(23,24)25/h6,8-10H,3-5,11H2,1-2H3,(H,27,28)

Standard InChI Key:  CZWJLLBPWLUINU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   -0.1746    2.3361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372    1.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5372    1.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3220    2.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8070    1.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5355    0.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055   -0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2624   -1.0721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4657   -1.2857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0165   -0.5938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6038    0.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6900   -0.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.6900   -0.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9758   -1.3744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9758   -2.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2616   -2.6114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6900   -2.6114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4525   -2.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2322   -2.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2616   -0.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5707    1.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7841    2.6114    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197    0.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7339   -0.2485    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4328    0.8793    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6082    0.8793    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
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 22 23  1  0
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 23 25  2  0
 24 26  1  0
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 13 27  1  0
 22 28  1  0
 29 19  1  0
 29 30  3  0
 11 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5093741

   ---

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: 468.44

Molecular Weight (Monoisotopic): 468.1634

AlogP: 3.47

#Rotatable Bonds: ┄

Polar Surface Area: 108.42

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.70

CX Basic pKa: 2.59

CX LogP: 1.89

CX LogD: 1.89

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.43

Np Likeness Score: -0.76

References

1. Powell CE, Hatcher JM, Jiang J, Vatsan PS, Che J, Gray NS..  (2022)  Selective Macrocyclic Inhibitors of DYRK1A/B.,  13  (4.0): [PMID:35450378] [10.1021/acsmedchemlett.1c00630]

2. Lindberg MF, Deau E, Arfwedson J, George N, George P, Alfonso P, Corrionero A, Meijer L..  (2023)  Comparative Efficacy and Selectivity of Pharmacological Inhibitors of DYRK and CLK Protein Kinases.,  66  (6): [PMID:36876904] [10.1021/acs.jmedchem.2c02068]

Source

Source(1):

• Scientific Literature