5-Chloro-2-((2S,4S)-4-fluoro-1-(9H-purin-6-yl)pyrrolidin-2-yl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

ID: ALA4548876

PubChem CID: 72949203

Max Phase: Preclinical

Molecular Formula: C21H16ClFN8O

Molecular Weight: 450.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1c2c(Cl)ccn2nc([C@@H]2C[C@H](F)CN2c2ncnc3[nH]cnc23)n1-c1ccccc1

Standard InChI:  InChI=1S/C21H16ClFN8O/c22-14-6-7-30-17(14)21(32)31(13-4-2-1-3-5-13)19(28-30)15-8-12(23)9-29(15)20-16-18(25-10-24-16)26-11-27-20/h1-7,10-12,15H,8-9H2,(H,24,25,26,27)/t12-,15-/m0/s1

Standard InChI Key:  YKETZZCLYKIFPU-WFASDCNBSA-N

Molfile:  

 
     RDKit          2D

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   24.9258  -14.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9258  -13.5593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2137  -13.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5017  -14.3844    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5017  -13.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7170  -13.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2320  -13.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7170  -14.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6379  -13.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3515  -13.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0667  -13.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.3513  -11.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   26.9463  -15.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3950  -14.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1143  -16.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3293  -15.9088    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7158  -16.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8859  -17.2675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2853  -16.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6772  -17.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0128  -18.2691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8284  -18.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9967  -17.3784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2137  -12.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4622  -12.5196    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   27.7669  -14.9916    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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  3 10  1  0
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 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
 16  2  1  6
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 26  1  0
 25 21  1  0
 17 21  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 25  1  0
  4 30  2  0
  7 31  1  0
 19 32  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4548876

   5-chloro-2-[(2S,4S)-4-fluoro-1-(7H-purin-6-yl)pyrrolidin-2-yl]-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4-one

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: 450.87

Molecular Weight (Monoisotopic): 450.1120

AlogP: 3.09

#Rotatable Bonds: 3

Polar Surface Area: 97.00

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.83

CX Basic pKa: 3.04

CX LogP: 2.55

CX LogD: 2.55

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.45

Np Likeness Score: -1.08

References

1. Jia H, Dai G, Su W, Xiao K, Weng J, Zhang Z, Wang Q, Yuan T, Shi F, Zhang Z, Chen W, Sai Y, Wang J, Li X, Cai Y, Yu J, Ren P, Venable J, Rao T, Edwards JP, Bembenek SD..  (2019)  Discovery, Optimization, and Evaluation of Potent and Highly Selective PI3Kγ-PI3Kδ Dual Inhibitors.,  62  (10): [PMID:31033293] [10.1021/acs.jmedchem.8b02014]

Source

Source(1):

• Scientific Literature