7-(4-Fluorobenzyl)-2-(methylthio)-4-morpholin-4-yl-7H-pyrrolo[2,3-d]pyrimidine

ID: ALA4100526

PubChem CID: 137659108

Max Phase: Preclinical

Molecular Formula: C18H19FN4OS

Molecular Weight: 358.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1nc(N2CCOCC2)c2ccn(Cc3ccc(F)cc3)c2n1

Standard InChI:  InChI=1S/C18H19FN4OS/c1-25-18-20-16(22-8-10-24-11-9-22)15-6-7-23(17(15)21-18)12-13-2-4-14(19)5-3-13/h2-7H,8-12H2,1H3

Standard InChI Key:  QGGIXKZOWARZOR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    8.6021  -18.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3102  -18.7691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0317  -18.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0410  -17.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3329  -17.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6115  -17.5238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8116  -18.6296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8266  -17.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3037  -17.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3423  -16.2945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0596  -15.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0689  -15.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3608  -14.6448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6435  -15.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6300  -15.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8848  -18.7530    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1725  -18.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0589  -19.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8648  -19.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1080  -20.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9139  -20.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4727  -19.9633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2295  -19.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4236  -18.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2786  -20.1418    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  8  9  2  0
  7  9  1  0
  3  7  1  0
  4  8  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 10 15  1  0
  5 10  1  0
 16 17  1  0
  1 16  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 19 24  2  0
 22 25  1  0
  7 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100526

   ---

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: 358.44

Molecular Weight (Monoisotopic): 358.1264

AlogP: 3.18

#Rotatable Bonds: 4

Polar Surface Area: 43.18

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.16

CX LogP: 4.40

CX LogD: 4.37

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: -2.02

References

1. Musumeci F, Fallacara AL, Brullo C, Grossi G, Botta L, Calandro P, Chiariello M, Kissova M, Crespan E, Maga G, Schenone S..  (2017)  Identification of new pyrrolo[2,3-d]pyrimidines as Src tyrosine kinase inhibitors in vitro active against Glioblastoma.,  127  [PMID:28076826] [10.1016/j.ejmech.2016.12.036]

Source

Source(1):

• Scientific Literature