9-Fluoro-3-((trans-4-hydroxycyclohexyl)amino)-11-methylbenzo[f]pyrido[4,3-b][1,4]oxazepin-10(11H)-one

ID: ALA4763016

PubChem CID: 124182258

Max Phase: Preclinical

Molecular Formula: C19H20FN3O3

Molecular Weight: 357.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1C(=O)c2c(F)cccc2Oc2cc(N[C@H]3CC[C@H](O)CC3)ncc21

Standard InChI:  InChI=1S/C19H20FN3O3/c1-23-14-10-21-17(22-11-5-7-12(24)8-6-11)9-16(14)26-15-4-2-3-13(20)18(15)19(23)25/h2-4,9-12,24H,5-8H2,1H3,(H,21,22)/t11-,12-

Standard InChI Key:  GFDDTDKCZCGJLM-HAQNSBGRSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   25.8290  -18.6604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8278  -19.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5405  -19.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5387  -18.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2568  -19.4823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2519  -18.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8971  -18.1324    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9110  -19.9953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7068  -18.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0705  -19.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7199  -19.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1945  -20.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0197  -20.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3679  -19.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8912  -18.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2136  -17.6583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7052  -17.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1152  -19.8959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1146  -20.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4025  -21.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3998  -21.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1100  -22.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8245  -21.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8288  -21.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1063  -23.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.2360  -18.2295    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  5  2  0
  6  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  7  9  1  0
  8 11  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  9 16  2  0
  7 17  1  0
  2 18  1  0
 19 18  1  1
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  6
 15 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4763016

   ---

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: 357.39

Molecular Weight (Monoisotopic): 357.1489

AlogP: 3.32

#Rotatable Bonds: 2

Polar Surface Area: 74.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.50

CX LogP: 1.86

CX LogD: 1.81

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.86

Np Likeness Score: -0.69

References

1. Sato M,Kondo T,Kohno Y,Seto S.  (2021)  Discovery of benzo[f]pyrido[4,3-b][1,4]oxazepin-10-one derivatives as orally available bromodomain and extra-terminal domain (BET) inhibitors with efficacy in an in vivo psoriatic animal model.,  34  [PMID:33549905] [10.1016/j.bmc.2021.116015]

Source

Source(1):

• Scientific Literature