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

ID: ALA4558466

PubChem CID: 132245935

Max Phase: Preclinical

Molecular Formula: C21H19N5O2S

Molecular Weight: 405.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CC(n2cc(-c3cc4cccc(OC)c4s3)c3c(N)ncnc32)C1

Standard InChI:  InChI=1S/C21H19N5O2S/c1-3-17(27)25-8-13(9-25)26-10-14(18-20(22)23-11-24-21(18)26)16-7-12-5-4-6-15(28-2)19(12)29-16/h3-7,10-11,13H,1,8-9H2,2H3,(H2,22,23,24)

Standard InChI Key:  WYSRIBSZOQNKSS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    8.7937  -12.8687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7926  -13.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5047  -14.1013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5029  -12.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2157  -12.8651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2205  -13.6878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0046  -13.9363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4861  -13.2670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9969  -12.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5005  -11.6344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2449  -11.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0221  -11.5641    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7582  -11.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2345  -10.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0156  -10.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6217  -10.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4479   -9.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6627   -9.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0599   -9.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4043  -10.4442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0128   -9.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2604  -14.7123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8936  -15.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6280  -15.8134    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9947  -15.0790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8369  -16.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2537  -17.1846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6299  -16.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2131  -16.2404    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
  4 10  1  0
  9 11  1  0
 11 12  1  0
 12 15  1  0
 14 13  1  0
 13 11  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16 20  1  0
 20 21  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 22  1  0
  7 22  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558466

   ---

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: 405.48

Molecular Weight (Monoisotopic): 405.1259

AlogP: 3.47

#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: 6.47

CX LogP: 2.76

CX LogD: 2.71

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.55

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