1-((3S)-3-(8-(1-ethyl-2-methyl-1H-pyrrol-3-yl)-9-methyl-9H-purin-6-ylamino)pyrrolidin-1-yl)propan-1-one

ID: ALA4877831

PubChem CID: 164626611

Max Phase: Preclinical

Molecular Formula: C20H27N7O

Molecular Weight: 381.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCC(=O)N1CC[C@H](Nc2ncnc3c2nc(-c2ccn(CC)c2C)n3C)C1

Standard InChI:  InChI=1S/C20H27N7O/c1-5-16(28)27-9-7-14(11-27)23-18-17-20(22-12-21-18)25(4)19(24-17)15-8-10-26(6-2)13(15)3/h8,10,12,14H,5-7,9,11H2,1-4H3,(H,21,22,23)/t14-/m0/s1

Standard InChI Key:  QLJLCTNLDTWEAZ-AWEZNQCLSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   32.4070  -14.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4029  -13.9583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1085  -13.5461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8529  -13.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3966  -13.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9844  -12.5566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1860  -12.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3130  -11.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1252  -11.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4538  -10.9706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8293  -11.1498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4131  -16.4081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1211  -15.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1138  -15.1764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.7028  -16.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6972  -15.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9210  -14.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4469  -15.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9301  -16.2591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6298  -15.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6830  -17.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1441  -14.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3689  -15.2118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3751  -16.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1541  -16.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3920  -14.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7050  -14.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9608  -15.0719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  3  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
  1 16  2  0
 15 12  2  0
 12 13  1  0
 13 14  2  0
 14  1  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 15  1  0
 18 20  1  0
 19 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 22 26  1  0
 23 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877831

   ---

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: 381.48

Molecular Weight (Monoisotopic): 381.2277

AlogP: 2.58

#Rotatable Bonds: 5

Polar Surface Area: 80.87

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.47

CX LogP: 1.77

CX LogD: 1.77

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.73

Np Likeness Score: -1.33

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