7-(4-Fluorobenzyl)-2-(methylthio)-4-pyrrolidin-1-yl-7H-pyrrolo[2,3-d]pyrimidine

ID: ALA4088440

PubChem CID: 137642749

Max Phase: Preclinical

Molecular Formula: C18H19FN4S

Molecular Weight: 342.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1nc(N2CCCC2)c2ccn(Cc3ccc(F)cc3)c2n1

Standard InChI:  InChI=1S/C18H19FN4S/c1-24-18-20-16(22-9-2-3-10-22)15-8-11-23(17(15)21-18)12-13-4-6-14(19)7-5-13/h4-8,11H,2-3,9-10,12H2,1H3

Standard InChI Key:  BBTSLIHTQGHZBD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    8.9506  -17.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6699  -18.0545    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3759  -17.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3626  -16.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6433  -16.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9332  -16.8289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1668  -17.8700    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1454  -16.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6407  -17.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6301  -15.5803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2866  -15.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0179  -14.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1932  -14.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9538  -15.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2404  -18.0775    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.5213  -17.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4355  -18.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2460  -18.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5147  -19.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3212  -19.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8630  -19.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5944  -18.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7879  -18.1870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6736  -19.2826    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
 10 14  1  0
  5 10  1  0
 15 16  1  0
  1 15  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 18 23  2  0
 21 24  1  0
  7 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088440

   ---

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: 342.44

Molecular Weight (Monoisotopic): 342.1314

AlogP: 3.94

#Rotatable Bonds: 4

Polar Surface Area: 33.95

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.20

CX LogP: 5.02

CX LogD: 5.00

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.53

Np Likeness Score: -1.90

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