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

ID: ALA4878995

PubChem CID: 90168940

Max Phase: Preclinical

Molecular Formula: C21H26N8O

Molecular Weight: 406.49

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H26N8O/c1-3-29-19(15-9-22-13(2)23-10-15)27-17-18(24-12-25-20(17)29)26-16-7-8-28(11-16)21(30)14-5-4-6-14/h9-10,12,14,16H,3-8,11H2,1-2H3,(H,24,25,26)/t16-/m0/s1

Standard InChI Key:  JLHUINFRYGKMQX-INIZCTEOSA-N

Molfile:  

 
     RDKit          2D

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   31.6352  -13.3763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3408  -12.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0852  -13.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6290  -12.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2168  -11.9747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.4184  -12.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5453  -11.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3576  -11.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0616  -10.5678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6455  -15.8261    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3534  -15.4096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3462  -14.5945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9352  -15.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9295  -14.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1534  -14.3597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6792  -15.0218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1625  -15.6772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8621  -15.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9153  -16.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4508  -14.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6757  -14.2778    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2304  -15.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6487  -15.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4637  -15.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4132  -15.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1172  -16.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9921  -11.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5031  -11.0112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8654  -10.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
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  5  6  1  0
  6  7  1  0
  7  3  1  0
  6  8  1  0
  8  9  1  0
  8 10  2  0
  1 15  2  0
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 11 12  1  0
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 17 18  1  0
 18 14  1  0
 17 19  1  0
 18 20  1  0
 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:

   

   ALA4878995

   cyclobutyl-[(3S)-3-[[9-ethyl-8-(2-methylpyrimidin-5-yl)purin-6-yl]amino]pyrrolidin-1-yl]methanone

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: 406.49

Molecular Weight (Monoisotopic): 406.2230

AlogP: 2.42

#Rotatable Bonds: 5

Polar Surface Area: 101.72

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.43

CX LogP: 1.45

CX LogD: 1.45

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.69

Np Likeness Score: -1.50

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