5-[2-Amino-3-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]-pyrimidin-5-yl]-2-[(1S)-1-cyclopropylethyl]-7-methyl-2,3-dihydro-1H-isoindol-1-one

ID: ALA4755842

PubChem CID: 162655810

Max Phase: Preclinical

Molecular Formula: C24H25N7O

Molecular Weight: 427.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2ccn3nc(N)c(-c4cnn(C)c4)c3n2)cc2c1C(=O)N([C@@H](C)C1CC1)C2

Standard InChI:  InChI=1S/C24H25N7O/c1-13-8-16(9-17-12-30(24(32)20(13)17)14(2)15-4-5-15)19-6-7-31-23(27-19)21(22(25)28-31)18-10-26-29(3)11-18/h6-11,14-15H,4-5,12H2,1-3H3,(H2,25,28)/t14-/m0/s1

Standard InChI Key:  FACINUDEPGDOCE-AWEZNQCLSA-N

Molfile:  

 
     RDKit          2D

 32 37  0  0  0  0  0  0  0  0999 V2000
   29.4624  -21.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1750  -22.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1749  -23.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8902  -23.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8861  -21.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6019  -22.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6090  -23.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3977  -23.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8797  -22.6985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3862  -22.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8915  -24.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7051  -22.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1218  -23.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1097  -21.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1296  -24.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8414  -23.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4645  -21.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7570  -20.6565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7587  -22.3010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0465  -21.8960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0411  -21.0737    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2571  -20.8259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7763  -21.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2658  -22.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9509  -21.5005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0153  -22.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2359  -23.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2412  -24.0314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0240  -24.2801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5065  -23.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5758  -24.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6576  -24.1554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  7  2  0
  6  5  2  0
  5  2  1  0
  1  2  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
  4 11  1  0
  9 12  1  0
 12 13  1  1
 12 14  1  0
 15 13  1  0
 16 15  1  0
 13 16  1  0
  1 17  1  0
 17 18  2  0
 18 21  1  0
 20 19  1  0
 19  1  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 20  2  0
 23 25  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 26  1  0
 24 26  1  0
 28 31  1  0
  8 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4755842

   ---

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: 427.51

Molecular Weight (Monoisotopic): 427.2121

AlogP: 3.44

#Rotatable Bonds: 4

Polar Surface Area: 94.34

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.97

CX Basic pKa: 2.73

CX LogP: 3.29

CX LogD: 3.29

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: -1.19

References

1. Drew SL,Thomas-Tran R,Beatty JW,Fournier J,Lawson KV,Miles DH,Mata G,Sharif EU,Yan X,Mailyan AK,Ginn E,Chen J,Wong K,Soni D,Dhanota P,Chen PY,Shaqfeh SG,Meleza C,Pham AT,Chen A,Zhao X,Banuelos J,Jin L,Schindler U,Walters MJ,Young SW,Walker NP,Leleti MR,Powers JP,Jeffrey JL.  (2020)  Discovery of Potent and Selective PI3Kγ Inhibitors.,  63  (19.0): [PMID:32865410] [10.1021/acs.jmedchem.0c01203]

2. Mata G, Miles DH, Drew SL, Fournier J, Lawson KV, Mailyan AK, Sharif EU, Yan X, Beatty JW, Banuelos J, Chen J, Ginn E, Chen A, Gerrick KY, Pham AT, Wong K, Soni D, Dhanota P, Shaqfeh SG, Meleza C, Narasappa N, Singh H, Zhao X, Jin L, Schindler U, Walters MJ, Young SW, Walker NP, Leleti MR, Powers JP, Jeffrey JL..  (2022)  Design, Synthesis, and Structure-Activity Relationship Optimization of Pyrazolopyrimidine Amide Inhibitors of Phosphoinositide 3-Kinase γ (PI3Kγ).,  65  (2.0): [PMID:34672584] [10.1021/acs.jmedchem.1c01153]

Source

Source(1):

• Scientific Literature