N-(5-(6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-4-morpholinopyrrolo[1,2-f][1,2,4]triazin-2-yl)-4-(trifluoromethyl)pyridin-2-yl)acrylamide

ID: ALA4740055

PubChem CID: 162645185

Max Phase: Preclinical

Molecular Formula: C25H29F3N8O4S

Molecular Weight: 594.62

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)Nc1cc(C(F)(F)F)c(-c2nc(N3CCOCC3)c3cc(CN4CCN(S(C)(=O)=O)CC4)cn3n2)cn1

Standard InChI:  InChI=1S/C25H29F3N8O4S/c1-3-22(37)30-21-13-19(25(26,27)28)18(14-29-21)23-31-24(34-8-10-40-11-9-34)20-12-17(16-36(20)32-23)15-33-4-6-35(7-5-33)41(2,38)39/h3,12-14,16H,1,4-11,15H2,2H3,(H,29,30,37)

Standard InChI Key:  OAQAPGBFBJSIFA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 41 45  0  0  0  0  0  0  0  0999 V2000
   20.2983   -3.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1133   -3.6318    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.7038   -2.9246    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.7552   -6.8657    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.0466   -6.4569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0435   -7.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1841   -4.8536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8894   -4.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8894   -3.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1841   -3.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4788   -4.4492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4788   -3.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6974   -3.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2143   -4.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6973   -4.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1832   -2.3987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8999   -1.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9010   -1.1728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1918   -0.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4798   -1.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4770   -1.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5947   -4.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5921   -5.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2984   -6.0855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0077   -5.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0063   -4.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2994   -4.4507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7137   -6.0899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3971   -4.0382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9885   -4.7459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1699   -4.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7614   -5.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1665   -6.1595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9847   -6.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3977   -5.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1612   -7.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5901   -3.2258    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.4233   -5.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1291   -6.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4271   -4.8674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8387   -5.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  5  4  2  0
  4  6  2  0
 12 10  1  0
 11  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 11  1  0
 10 16  1  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
  8 22  1  0
 25 28  1  0
 14 29  1  0
 29 30  1  0
 30 31  1  0
 30 35  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 33  4  1  0
  4 36  1  0
 27  1  1  0
  1 37  1  0
 28 38  1  0
 38 39  1  0
 38 40  2  0
 39 41  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4740055

   ---

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: 594.62

Molecular Weight (Monoisotopic): 594.1985

AlogP: 1.85

#Rotatable Bonds: 7

Polar Surface Area: 125.27

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.07

CX Basic pKa: 5.59

CX LogP: 2.86

CX LogD: 2.85

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.41

Np Likeness Score: -1.73

References

1. Xiang HY,Wang X,Chen YH,Zhang X,Tan C,Wang Y,Su Y,Gao ZW,Chen XY,Xiong B,Gao ZB,Chen Y,Ding J,Meng LH,Yang CH.  (2021)  Identification of methyl (5-(6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-2-yl)-4-(trifluoromethyl)pyridin-2-yl)carbamate (CYH33) as an orally bioavailable, highly potent, PI3K alpha inhibitor for the treatment of advanced solid tumors.,  209  [PMID:33109399] [10.1016/j.ejmech.2020.112913]

Source

Source(1):

• Scientific Literature