6-(4-(1H-1,2,4-triazol-3-yl)phenyl)-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one

ID: ALA2348865

Cas Number: 1021920-32-0

PubChem CID: 66699750

Max Phase: Preclinical

Molecular Formula: C20H21N7O2

Molecular Weight: 391.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c2ncc(-c3ccc(-c4nc[nH]n4)cc3)nc2n1CCC1CCOCC1

Standard InChI:  InChI=1S/C20H21N7O2/c28-20-25-18-19(27(20)8-5-13-6-9-29-10-7-13)24-16(11-21-18)14-1-3-15(4-2-14)17-22-12-23-26-17/h1-4,11-13H,5-10H2,(H,21,25,28)(H,22,23,26)

Standard InChI Key:  FFGUSRSMWFYKGK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    4.2204  -11.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2196  -12.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9276  -12.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6373  -12.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6345  -11.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9258  -10.9492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3421  -12.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3421  -13.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0496  -13.8096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0456  -12.1747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5301  -12.3213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7537  -12.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7602  -13.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417  -13.6430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0156  -12.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8327  -12.9665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9495  -11.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411  -10.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5141  -10.0873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7278   -9.8614    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710  -10.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7767  -11.1837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7666  -11.6325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1861  -10.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0016  -10.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4209  -10.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0267   -9.5322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2087   -9.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7849  -10.2194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  7  8  2  0
  8  9  1  0
  9 13  2  0
 12 10  2  0
 10  7  1  0
  4  7  1  0
 12 13  1  0
 11 12  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 15 16  2  0
 11 17  1  0
 19 20  1  0
 18 19  2  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
  1 18  1  0
 17 23  1  0
 23 24  1  0
 24 25  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2348865

   3-[2-(oxan-4-yl)ethyl]-5-[4-(1H-1,2,4-triazol-5-yl)phenyl]-1H-imidazo[4,5-b]pyrazin-2-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 391.44

Molecular Weight (Monoisotopic): 391.1757

AlogP: 2.39

#Rotatable Bonds: 5

Polar Surface Area: 114.37

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.97

CX Basic pKa: 1.53

CX LogP: 3.06

CX LogD: 3.06

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.54

Np Likeness Score: -1.34

References

1. Mortensen DS, Sapienza J, Lee BG, Perrin-Ninkovic SM, Harris R, Shevlin G, Parnes JS, Whitefield B, Hickman M, Khambatta G, Bisonette RR, Peng S, Gamez JC, Leisten J, Narla RK, Fultz KE, Sankar S..  (2013)  Use of core modification in the discovery of CC214-2, an orally available, selective inhibitor of mTOR kinase.,  23  (6): [PMID:23414803] [10.1016/j.bmcl.2013.01.110]

2. Mortensen DS, Perrin-Ninkovic SM, Shevlin G, Zhao J, Packard G, Bahmanyar S, Correa M, Elsner J, Harris R, Lee BG, Papa P, Parnes JS, Riggs JR, Sapienza J, Tehrani L, Whitefield B, Apuy J, Bisonette RR, Gamez JC, Hickman M, Khambatta G, Leisten J, Peng SX, Richardson SJ, Cathers BE, Canan SS, Moghaddam MF, Raymon HK, Worland P, Narla RK, Fultz KE, Sankar S..  (2015)  Discovery of mammalian target of rapamycin (mTOR) kinase inhibitor CC-223.,  58  (13): [PMID:26083478] [10.1021/acs.jmedchem.5b00626]

3. Fernandes GFDS, Fernandes BC, Valente V, Dos Santos JL..  (2019)  Recent advances in the discovery of small molecules targeting glioblastoma.,  164  [PMID:30583248] [10.1016/j.ejmech.2018.12.033]

4. Oleksak P, Nepovimova E, Chrienova Z, Musilek K, Patocka J, Kuca K..  (2022)  Contemporary mTOR inhibitor scaffolds to diseases breakdown: A patent review (2015-2021).,  238  [PMID:35688004] [10.1016/j.ejmech.2022.114498]

Source

Source(1):

• Scientific Literature