(S)-cyclobutyl(3-(9-ethyl-8-(2-methylpyrimidin-5-yl)-9H-purin-6-yloxy)pyrrolidin-1-yl)methanone

ID: ALA4873843

PubChem CID: 164619876

Max Phase: Preclinical

Molecular Formula: C21H25N7O2

Molecular Weight: 407.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCn1c(-c2cnc(C)nc2)nc2c(O[C@H]3CCN(C(=O)C4CCC4)C3)ncnc21

Standard InChI:  InChI=1S/C21H25N7O2/c1-3-28-18(15-9-22-13(2)23-10-15)26-17-19(28)24-12-25-20(17)30-16-7-8-27(11-16)21(29)14-5-4-6-14/h9-10,12,14,16H,3-8,11H2,1-2H3/t16-/m0/s1

Standard InChI Key:  AATSAMRSGNEIGC-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

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   40.3602  -14.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.3560  -13.7767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.0617  -13.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8061  -13.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3498  -13.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.9376  -12.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.1392  -12.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2661  -11.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.0784  -11.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.7824  -10.9682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.3663  -16.2265    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.0743  -15.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.0670  -14.9948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.6560  -15.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.6504  -15.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8742  -14.7601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.4001  -15.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8833  -16.0775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5830  -15.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6362  -16.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1716  -14.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3965  -14.6782    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.9512  -15.4390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3695  -16.1459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1845  -16.1366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1341  -15.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8380  -17.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7129  -12.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.2240  -11.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.5862  -10.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 10  2  0
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 17 19  1  0
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 19 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 19  1  0
 23 26  1  0
 20 27  1  0
  9 28  1  0
 28 29  1  0
 29 30  1  0
 30  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873843

   ---

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: 407.48

Molecular Weight (Monoisotopic): 407.2070

AlogP: 2.39

#Rotatable Bonds: 5

Polar Surface Area: 98.92

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.27

CX LogP: 1.70

CX LogD: 1.70

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.64

Np Likeness Score: -1.36

References

1. Methot JL, Zhou H, McGowan MA, Anthony NJ, Christopher M, Garcia Y, Achab A, Lipford K, Trotter BW, Altman MD, Fradera X, Lesburg CA, Li C, Alves S, Chappell CP, Jain R, Mangado R, Pinheiro E, Williams SMG, Goldenblatt P, Hill A, Shaffer L, Chen D, Tong V, McLeod RL, Lee HH, Yu H, Shah S, Katz JD..  (2021)  Projected Dose Optimization of Amino- and Hydroxypyrrolidine Purine PI3Kδ Immunomodulators.,  64  (8.0): [PMID:33797901] [10.1021/acs.jmedchem.1c00237]

Source

Source(1):

• Scientific Literature