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

ID: ALA4175249

PubChem CID: 145951943

Max Phase: Preclinical

Molecular Formula: C17H10F7NO2

Molecular Weight: 393.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(C(O)(C(F)(F)F)C(F)(F)F)cc2c1[nH]c(=O)c1cc(F)ccc12

Standard InChI:  InChI=1S/C17H10F7NO2/c1-7-4-8(15(27,16(19,20)21)17(22,23)24)5-11-10-3-2-9(18)6-12(10)14(26)25-13(7)11/h2-6,27H,1H3,(H,25,26)

Standard InChI Key:  OYKDEMAUDZHYTM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   11.0119  -11.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7146  -11.9236    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.8262  -11.0219    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.5278  -11.7955    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.7045  -11.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4165  -10.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1359   -9.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1347  -10.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8496  -10.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8478   -9.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5631   -9.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5619  -10.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9947   -9.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2772   -9.0224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9935  -10.2683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2754  -10.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2703  -11.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9826  -11.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7015  -11.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7030  -10.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7102   -9.0291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7058  -10.2677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9876  -10.6874    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.7094  -11.9206    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.9873  -11.5040    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.8452   -8.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4151  -11.9185    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
 19 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4175249

   ---

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: 393.26

Molecular Weight (Monoisotopic): 393.0600

AlogP: 4.44

#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: 7.40

CX Basic pKa: ┄

CX LogP: 4.52

CX LogD: 4.22

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.47

Np Likeness Score: -0.58

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