1-(3-(4-Amino-5-(7-methoxybenzo[b]thiophen-2-yl)-7H-pyrrolo-[2,3-d]pyrimidin-7-yl)pyrrolidin-1-yl)prop-2-en-1-one

ID: ALA4580623

PubChem CID: 132246051

Max Phase: Preclinical

Molecular Formula: C22H21N5O2S

Molecular Weight: 419.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CCC(n2cc(-c3cc4cccc(OC)c4s3)c3c(N)ncnc32)C1

Standard InChI:  InChI=1S/C22H21N5O2S/c1-3-18(28)26-8-7-14(10-26)27-11-15(19-21(23)24-12-25-22(19)27)17-9-13-5-4-6-16(29-2)20(13)30-17/h3-6,9,11-12,14H,1,7-8,10H2,2H3,(H2,23,24,25)

Standard InChI Key:  QWGUTUKCPRERRM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    2.1324  -12.5921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1312  -13.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393  -13.8206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375  -12.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5461  -12.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5509  -13.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3309  -13.6556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8083  -12.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3232  -12.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5880  -14.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8350  -11.3661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5711  -11.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1154  -15.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5996  -15.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3754  -15.4957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3705  -14.6786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794  -15.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0794  -16.7194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7871  -15.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4948  -15.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3443  -11.2958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844  -10.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5608  -10.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3377  -10.4796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9397   -9.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7659   -9.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9848   -8.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3862   -9.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7182  -10.1801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3226   -9.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  7 10  1  0
  4 11  1  0
  9 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 10  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 12 21  1  0
 21 24  1  0
 23 22  1  0
 22 12  2  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 25 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4580623

   ---

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: 419.51

Molecular Weight (Monoisotopic): 419.1416

AlogP: 3.86

#Rotatable Bonds: 4

Polar Surface Area: 86.27

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.48

CX LogP: 2.82

CX LogD: 2.77

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: -0.70

References

1. Wang Y, Li L, Fan J, Dai Y, Jiang A, Geng M, Ai J, Duan W..  (2018)  Discovery of Potent Irreversible Pan-Fibroblast Growth Factor Receptor (FGFR) Inhibitors.,  61  (20): [PMID:29522671] [10.1021/acs.jmedchem.7b01843]

Source

Source(1):

• Scientific Literature