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

ID: ALA4591002

PubChem CID: 155568305

Max Phase: Preclinical

Molecular Formula: C21H19N5O2

Molecular Weight: 373.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CCC(n2cc(-c3cc4ccccc4o3)c3c(N)ncnc32)C1

Standard InChI:  InChI=1S/C21H19N5O2/c1-2-18(27)25-8-7-14(10-25)26-11-15(19-20(22)23-12-24-21(19)26)17-9-13-5-3-4-6-16(13)28-17/h2-6,9,11-12,14H,1,7-8,10H2,(H2,22,23,24)

Standard InChI Key:  RVDPIUBBAZZMPR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   18.2038  -23.7233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2026  -24.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9148  -24.9559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9130  -23.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6258  -23.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6306  -24.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4147  -24.7909    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.8962  -24.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4070  -23.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6718  -25.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9106  -22.4890    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6549  -22.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1992  -26.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6834  -26.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4633  -26.6392    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4584  -25.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1715  -27.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1715  -27.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8833  -26.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5951  -27.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4322  -22.4187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1683  -22.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6446  -21.3494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4256  -21.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0318  -21.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8580  -20.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0728  -19.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4700  -20.5529    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
M  END

Alternative Forms

1. Parent:

   

   ALA4591002

   ---

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: 373.42

Molecular Weight (Monoisotopic): 373.1539

AlogP: 3.39

#Rotatable Bonds: 3

Polar Surface Area: 90.18

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.37

CX LogP: 2.18

CX LogD: 2.14

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: -0.31

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