(S)-2-(1-(2-Amino-5-chloropyrimidin-4-yl)azetidin-2-yl)-5-chloro-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

ID: ALA4536678

PubChem CID: 118445928

Max Phase: Preclinical

Molecular Formula: C19H15Cl2N7O

Molecular Weight: 428.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1ncc(Cl)c(N2CC[C@H]2c2nn3ccc(Cl)c3c(=O)n2-c2ccccc2)n1

Standard InChI:  InChI=1S/C19H15Cl2N7O/c20-12-6-9-27-15(12)18(29)28(11-4-2-1-3-5-11)17(25-27)14-7-8-26(14)16-13(21)10-23-19(22)24-16/h1-6,9-10,14H,7-8H2,(H2,22,23,24)/t14-/m0/s1

Standard InChI Key:  NLNBVPURMACCHY-AWEZNQCLSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   24.2797  -15.4715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9918  -15.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9918  -14.2381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2797  -13.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5676  -15.0631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5676  -14.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7831  -13.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2981  -14.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7830  -15.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7038  -13.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4173  -14.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1325  -13.8363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1355  -13.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4171  -12.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7049  -13.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7067  -15.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2797  -12.9964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5282  -13.1985    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.9185  -16.2735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7161  -16.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5026  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5087  -16.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6825  -16.9839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2693  -17.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6810  -18.4130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9199  -17.6976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5129  -18.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4443  -17.6957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7449  -17.6951    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  3 10  1  0
 16  2  1  6
  4 17  2  0
  7 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 16  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 27  1  0
 26 22  1  0
 19 22  1  0
 26 27  2  0
 24 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4536678

   2-[(2S)-1-(2-amino-5-chloropyrimidin-4-yl)azetidin-2-yl]-5-chloro-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4-one

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: 428.28

Molecular Weight (Monoisotopic): 427.0715

AlogP: 3.12

#Rotatable Bonds: 3

Polar Surface Area: 94.34

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.33

CX LogP: 3.09

CX LogD: 3.09

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: -1.15

References

1. Jia H, Dai G, Su W, Xiao K, Weng J, Zhang Z, Wang Q, Yuan T, Shi F, Zhang Z, Chen W, Sai Y, Wang J, Li X, Cai Y, Yu J, Ren P, Venable J, Rao T, Edwards JP, Bembenek SD..  (2019)  Discovery, Optimization, and Evaluation of Potent and Highly Selective PI3Kγ-PI3Kδ Dual Inhibitors.,  62  (10): [PMID:31033293] [10.1021/acs.jmedchem.8b02014]

Source

Source(1):

• Scientific Literature