4-Fluoro-2-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenanthridin-6(5H)-one

ID: ALA4174942

PubChem CID: 145949365

Max Phase: Preclinical

Molecular Formula: C16H8F7NO2

Molecular Weight: 379.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c2c(F)cc(C(O)(C(F)(F)F)C(F)(F)F)cc2c2ccccc12

Standard InChI:  InChI=1S/C16H8F7NO2/c17-11-6-7(14(26,15(18,19)20)16(21,22)23)5-10-8-3-1-2-4-9(8)13(25)24-12(10)11/h1-6,26H,(H,24,25)

Standard InChI Key:  CMSGVURZCKVOGX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   41.7217  -28.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4272  -29.2938    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   42.5283  -28.4007    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   42.2328  -29.1670    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   40.4267  -28.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1320  -28.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8446  -26.8352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8434  -27.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5515  -28.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5497  -26.4263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2583  -26.8316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2571  -27.6522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6764  -26.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9656  -26.4200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   44.6752  -27.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9638  -28.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9588  -28.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6644  -29.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3765  -28.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3780  -28.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3851  -26.4267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4280  -27.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.7166  -28.0693    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   40.4315  -29.2909    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   39.7163  -28.8782    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   42.5472  -25.6092    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  8  9  1  0
  9 12  2  0
 11 10  2  0
 10  7  1  0
 11 12  1  0
 11 14  1  0
 12 16  1  0
 15 13  1  0
 13 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 13 21  2  0
  8  6  1  0
  6 22  1  0
  5 23  1  0
  5 24  1  0
  5 25  1  0
 10 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4174942

   ---

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: 379.23

Molecular Weight (Monoisotopic): 379.0443

AlogP: 4.13

#Rotatable Bonds: 1

Polar Surface Area: 53.09

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.29

CX Basic pKa: ┄

CX LogP: 4.01

CX LogD: 3.65

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.49

Np Likeness Score: -0.50

References

1. Nishiyama Y, Mori S, Makishima M, Fujii S, Kagechika H, Hashimoto Y, Ishikawa M..  (2018)  Novel Nonsteroidal Progesterone Receptor (PR) Antagonists with a Phenanthridinone Skeleton.,  9  (7): [PMID:30034593] [10.1021/acsmedchemlett.8b00058]

Source

Source(1):

• Scientific Literature