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

ID: ALA4575973

PubChem CID: 155564268

Max Phase: Preclinical

Molecular Formula: C21H19N5O2S

Molecular Weight: 405.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CC(n2cc(-c3cc4cc(OC)ccc4s3)c3c(N)ncnc32)C1

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

Standard InChI Key:  HZPFRBXNIBOLLW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
   22.5952  -13.3103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5940  -14.1339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3062  -14.5470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3044  -12.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0171  -13.3067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0219  -14.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8061  -14.3820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2835  -13.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7983  -13.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3020  -12.0801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0463  -12.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8236  -12.0098    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.5555  -11.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0360  -10.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8170  -11.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4231  -10.6374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2453   -9.8364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4600   -9.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8614  -10.1440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0618  -15.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6950  -15.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4253  -16.2592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.7962  -15.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6383  -17.0496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0552  -17.6303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4314  -17.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0104  -16.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2827   -8.7885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8890   -8.2320    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
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 20  1  0
  7 20  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  2  0
 18 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4575973

   ---

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: 6.46

CX LogP: 2.76

CX LogD: 2.71

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.53

Np Likeness Score: -0.62

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