(R)-3-Fluoro-N-((1R,3S)-3-((5-fluoro-2-(5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl)amino)cyclohexyl)pyrrolidine-1-carboxamide

ID: ALA3985406

PubChem CID: 57385368

Max Phase: Preclinical

Molecular Formula: C21H23F3N8O

Molecular Weight: 460.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(N[C@@H]1CCC[C@H](Nc2nc(-c3n[nH]c4ncc(F)cc34)ncc2F)C1)N1CC[C@@H](F)C1

Standard InChI:  InChI=1S/C21H23F3N8O/c22-11-4-5-32(10-11)21(33)28-14-3-1-2-13(7-14)27-19-16(24)9-26-20(29-19)17-15-6-12(23)8-25-18(15)31-30-17/h6,8-9,11,13-14H,1-5,7,10H2,(H,28,33)(H,25,30,31)(H,26,27,29)/t11-,13+,14-/m1/s1

Standard InChI Key:  NFNZAFJHNGWPSZ-KWCYVHTRSA-N

Molfile:  

     RDKit          2D

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   24.3811   -4.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0891   -5.1163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0874   -3.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7960   -3.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7962   -4.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5792   -4.9616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   26.5788   -3.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6744   -3.4794    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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   27.6315   -2.6848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8839   -1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3366   -1.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5337   -1.4739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.2299   -2.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9733   -3.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5162   -3.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3168   -3.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5716   -2.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0258   -2.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3715   -2.6215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9162   -3.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7161   -3.0636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6609   -4.0070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3163   -3.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0254   -3.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8584   -2.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0460   -2.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4073   -1.8008    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  9  5  1  0
  1 10  1  0
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  9 11  1  0
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 19 18  1  6
 19 20  1  0
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 20 21  1  0
 21 22  1  0
 22 23  1  0
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 23 25  1  6
 25 26  1  0
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 26 28  2  0
 27 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 27  1  0
 31 33  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3985406

   (3R)-3-fluoro-N-[(1R,3S)-3-[[5-fluoro-2-(5-fluoro-2H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-4-yl]amino]cyclohexyl]pyrrolidine-1-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: 460.46

Molecular Weight (Monoisotopic): 460.1947

AlogP: 3.17

#Rotatable Bonds: 4

Polar Surface Area: 111.72

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.89

CX Basic pKa: 0.76

CX LogP: 2.20

CX LogD: 2.20

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.55

Np Likeness Score: -1.55

References

1. Bandarage UK, Clark MP, Perola E, Gao H, Jacobs MD, Tsai A, Gillespie J, Kennedy JM, Maltais F, Ledeboer MW, Davies I, Gu W, Byrn RA, Nti Addae K, Bennett H, Leeman JR, Jones SM, O'Brien C, Memmott C, Bennani Y, Charifson PS..  (2017)  Novel 2-Substituted 7-Azaindole and 7-Azaindazole Analogues as Potential Antiviral Agents for the Treatment of Influenza.,  8  (2): [PMID:28197323] [10.1021/acsmedchemlett.6b00487]

Source

Source(1):

• Scientific Literature