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

ID: ALA4073713

PubChem CID: 137641213

Max Phase: Preclinical

Molecular Formula: C19H21FN4S

Molecular Weight: 356.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSc1nc(N2CCCCC2)c2ccn(Cc3ccc(F)cc3)c2n1

Standard InChI:  InChI=1S/C19H21FN4S/c1-25-19-21-17(23-10-3-2-4-11-23)16-9-12-24(18(16)22-19)13-14-5-7-15(20)8-6-14/h5-9,12H,2-4,10-11,13H2,1H3

Standard InChI Key:  WCTJLMVSZAACPV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
    9.8010  -19.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5161  -19.5624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2307  -19.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2259  -18.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5066  -17.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7962  -18.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0151  -19.3973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0072  -18.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4958  -18.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5018  -17.0876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2121  -16.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2072  -15.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4921  -15.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7775  -15.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7865  -16.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0864  -19.5749    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.3712  -19.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2757  -20.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0848  -20.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3413  -21.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1504  -21.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6987  -20.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4380  -19.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6331  -19.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5077  -20.8460    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:

   

   ALA4073713

   ---

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: 356.47

Molecular Weight (Monoisotopic): 356.1471

AlogP: 4.33

#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: 5.47

CX LogD: 5.44

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: -1.83

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