6-N-[3-chloro-4-(3-fluorobenzyloxy)phenyl]-8-(furan-2-yl)-9H-purin-6-amine

ID: ALA4457175

PubChem CID: 155525531

Max Phase: Preclinical

Molecular Formula: C22H15ClFN5O2

Molecular Weight: 435.85

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Fc1cccc(COc2ccc(Nc3ncnc4[nH]c(-c5ccco5)nc34)cc2Cl)c1

Standard InChI:  InChI=1S/C22H15ClFN5O2/c23-16-10-15(6-7-17(16)31-11-13-3-1-4-14(24)9-13)27-21-19-22(26-12-25-21)29-20(28-19)18-5-2-8-30-18/h1-10,12H,11H2,(H2,25,26,27,28,29)

Standard InChI Key:  UTKSFIXFZBRYEI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    6.7354  -17.8529    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4450  -17.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4422  -16.6208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7336  -16.2156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0273  -17.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285  -16.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2523  -16.3739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7714  -17.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2504  -17.6951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511  -17.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4717  -16.3735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6941  -16.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6929  -17.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4698  -17.6957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7298  -15.3984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4356  -14.9865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1430  -15.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8484  -14.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8451  -14.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1305  -13.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4281  -14.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1238  -12.9451    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.5503  -13.7547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2604  -14.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9657  -13.7463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6733  -14.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3781  -13.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3737  -12.9218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6586  -12.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9567  -12.9321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6509  -11.7005    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
  8 10  1  0
  4 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4457175

   ---

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: 435.85

Molecular Weight (Monoisotopic): 435.0898

AlogP: 5.73

#Rotatable Bonds: 6

Polar Surface Area: 88.86

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.81

CX Basic pKa: 2.49

CX LogP: 5.14

CX LogD: 5.01

Aromatic Rings: 5

Heavy Atoms: 31

QED Weighted: 0.35

Np Likeness Score: -1.75

References

1. Gavriil ES, Doukatas A, Karampelas T, Myrianthopoulos V, Dimitrakis S, Mikros E, Marakos P, Tamvakopoulos C, Pouli N..  (2019)  Design, synthesis and biological evaluation of novel substituted purine isosters as EGFR kinase inhibitors, with promising pharmacokinetic profile and in vivo efficacy.,  176  [PMID:31125894] [10.1016/j.ejmech.2019.05.029]

Source

Source(1):

• Scientific Literature