N-(5-{2-[(1S)-1-Cyclopropylethyl]-1-oxo-7-(trifluoromethyl)-2,3-dihydro-1H-isoindol-5-yl}pyrazolo[1,5-a]pyrimidin-2-yl)acetamide

ID: ALA4785086

PubChem CID: 162665297

Max Phase: Preclinical

Molecular Formula: C22H20F3N5O2

Molecular Weight: 443.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cc2nc(-c3cc4c(c(C(F)(F)F)c3)C(=O)N([C@@H](C)C3CC3)C4)ccn2n1

Standard InChI:  InChI=1S/C22H20F3N5O2/c1-11(13-3-4-13)29-10-15-7-14(8-16(22(23,24)25)20(15)21(29)32)17-5-6-30-19(27-17)9-18(28-30)26-12(2)31/h5-9,11,13H,3-4,10H2,1-2H3,(H,26,28,31)/t11-/m0/s1

Standard InChI Key:  LFDGWINKLUZIEU-NSHDSACASA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    8.4200   -5.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1332   -6.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1331   -6.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8491   -7.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8451   -5.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5616   -6.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5686   -6.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3582   -7.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8365   -6.4076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3468   -5.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8504   -8.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6628   -6.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0841   -7.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0718   -5.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0918   -7.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8002   -7.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4236   -4.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7112   -4.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7099   -6.0112    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9969   -5.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9931   -4.7770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2075   -4.5258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7258   -5.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2137   -5.8602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9037   -5.1992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4893   -4.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6672   -4.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970   -3.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1392   -8.4880    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5631   -8.4857    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.8447   -8.8938    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.6215   -7.8640    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
 25 26  1  0
 26 27  1  0
 26 28  2  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
  8 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4785086

   ---

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: 443.43

Molecular Weight (Monoisotopic): 443.1569

AlogP: 4.13

#Rotatable Bonds: 4

Polar Surface Area: 79.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.28

CX Basic pKa: 0.46

CX LogP: 3.64

CX LogD: 3.64

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.66

Np Likeness Score: -1.09

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]

Source

Source(1):

• Scientific Literature