5,5-dimethyl-8-(4-(2,2,2-trifluoroethylamino)furo[3,2-d]pyrimidin-2-ylamino)-3,5-dihydrobenzo[e][1,4]oxazepin-2(1H)-one

ID: ALA4069365

PubChem CID: 137634241

Max Phase: Preclinical

Molecular Formula: C19H18F3N5O3

Molecular Weight: 421.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)OCC(=O)Nc2cc(Nc3nc(NCC(F)(F)F)c4occc4n3)ccc21

Standard InChI:  InChI=1S/C19H18F3N5O3/c1-18(2)11-4-3-10(7-13(11)25-14(28)8-30-18)24-17-26-12-5-6-29-15(12)16(27-17)23-9-19(20,21)22/h3-7H,8-9H2,1-2H3,(H,25,28)(H2,23,24,26,27)

Standard InChI Key:  IGRYEDIMNMEBBU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   29.0020  -18.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4148  -18.8986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8232  -18.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2501  -20.6512    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9598  -20.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9569  -19.4191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2483  -19.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2477  -18.1966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9550  -17.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9544  -16.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6618  -16.5611    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.2463  -16.5623    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.9479  -16.1498    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.6681  -20.6492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3752  -20.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0802  -20.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0726  -19.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3690  -19.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5396  -20.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5387  -19.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7602  -19.1691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2799  -19.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7616  -20.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7851  -20.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7802  -19.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4307  -20.7404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2154  -19.0739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2280  -20.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5743  -19.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7445  -21.1837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
 19  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7 20  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 16 24  1  0
 25 17  1  0
 17 18  2  0
 18 15  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 19  1  0
 24 25  2  0
 25  2  1  0
 24 26  1  0
  2 27  1  0
 26 28  1  0
 27 29  1  0
 28 29  1  0
 28 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4069365

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 421.38

Molecular Weight (Monoisotopic): 421.1362

AlogP: 4.14

#Rotatable Bonds: 4

Polar Surface Area: 101.31

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.11

CX Basic pKa: 3.73

CX LogP: 3.25

CX LogD: 3.25

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.58

Np Likeness Score: -0.64

References

1. Hoemann M, Wilson N, Argiriadi M, Banach D, Burchat A, Calderwood D, Clapham B, Cox P, Duignan DB, Konopacki D, Somal G, Vasudevan A..  (2016)  Synthesis and optimization of furano[3,2-d]pyrimidines as selective spleen tyrosine kinase (Syk) inhibitors.,  26  (22): [PMID:27789138] [10.1016/j.bmcl.2016.09.077]

Source

Source(1):

• Scientific Literature