3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-methyl-8-(1-methyl-1H-pyrazol-4-yl)-1,3,4,7-tetrahydro-2H-pyrrolo[3',2':5,6]pyrido[4,3-d]pyrimidin-2-one

ID: ALA4871581

PubChem CID: 164621178

Max Phase: Preclinical

Molecular Formula: C22H20F2N6O3

Molecular Weight: 454.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(F)c(N2Cc3cnc4[nH]c(-c5cnn(C)c5)cc4c3N(C)C2=O)c1F

Standard InChI:  InChI=1S/C22H20F2N6O3/c1-28-9-11(8-26-28)14-5-13-19-12(7-25-21(13)27-14)10-30(22(31)29(19)2)20-17(23)15(32-3)6-16(33-4)18(20)24/h5-9H,10H2,1-4H3,(H,25,27)

Standard InChI Key:  BEIAIBOGYLFZCK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
   19.9867   -5.6401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6978   -6.0491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4087   -5.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4087   -4.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6974   -4.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9867   -4.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2792   -4.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2792   -3.5873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9898   -3.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6974   -3.5902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4109   -3.1832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9898   -2.3589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5734   -3.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5734   -2.3585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8661   -1.9445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1536   -2.3560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1536   -3.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8644   -3.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8644   -4.4049    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.4424   -3.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7299   -3.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8661   -1.1232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1572   -0.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2856   -1.9526    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.1899   -4.5513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6792   -5.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1977   -5.8840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4975   -5.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9818   -5.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7575   -5.6102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7575   -4.7930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9740   -4.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4214   -6.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  4  3  1  0
  4  5  2  0
  6  5  1  0
  6  1  2  0
  6  7  1  0
  8  7  1  0
  9  8  1  0
 10  9  1  0
  5 10  1  0
 10 11  1  0
  9 12  2  0
  8 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 15 22  1  0
 22 23  1  0
 14 24  1  0
 25  4  1  0
 26 25  2  0
 27 26  1  0
  3 27  1  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 32 28  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4871581

   ---

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: 454.44

Molecular Weight (Monoisotopic): 454.1565

AlogP: 3.84

#Rotatable Bonds: 4

Polar Surface Area: 88.51

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.83

CX Basic pKa: 2.44

CX LogP: 1.81

CX LogD: 1.81

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.51

Np Likeness Score: -0.81

References

1. Wu L, Zhang C, He C, Qian D, Lu L, Sun Y, Xu M, Zhuo J, Liu PCC, Klabe R, Wynn R, Covington M, Gallagher K, Leffet L, Bowman K, Diamond S, Koblish H, Zhang Y, Soloviev M, Hollis G, Burn TC, Scherle P, Yeleswaram S, Huber R, Yao W..  (2021)  Discovery of Pemigatinib: A Potent and Selective Fibroblast Growth Factor Receptor (FGFR) Inhibitor.,  64  (15.0): [PMID:34269576] [10.1021/acs.jmedchem.1c00713]

Source

Source(1):

• Scientific Literature