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

ID: ALA3259994

PubChem CID: 25132505

Max Phase: Preclinical

Molecular Formula: C16H9F6NO2

Molecular Weight: 361.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1[nH]c2ccc(C(O)(C(F)(F)F)C(F)(F)F)cc2c2ccccc12

Standard InChI:  InChI=1S/C16H9F6NO2/c17-15(18,19)14(25,16(20,21)22)8-5-6-12-11(7-8)9-3-1-2-4-10(9)13(24)23-12/h1-7,25H,(H,23,24)

Standard InChI Key:  NKLTUBXOEGMKJS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   33.1155   -1.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1143   -2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8224   -3.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8206   -1.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5292   -1.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5280   -2.7531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9551   -1.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2405   -1.5141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.9539   -2.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2375   -3.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2326   -3.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9435   -4.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6607   -3.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6620   -3.1676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6638   -1.5231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4063   -3.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6989   -2.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9909   -3.1580    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.6996   -1.9327    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   30.9872   -2.3401    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.4056   -3.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6976   -4.3843    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.1130   -4.3854    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.3987   -4.7917    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   31.6930   -3.5618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6 10  1  0
  9  7  1  0
  7  8  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  7 15  2  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 16 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 16 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3259994

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

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: 361.24

Molecular Weight (Monoisotopic): 361.0537

AlogP: 3.99

#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: 7.38

CX Basic pKa: ┄

CX LogP: 3.87

CX LogD: 3.55

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: -0.42

References

1. Nishiyama Y, Nakamura M, Misawa T, Nakagomi M, Makishima M, Ishikawa M, Hashimoto Y..  (2014)  Structure-activity relationship-guided development of retinoic acid receptor-related orphan receptor gamma (RORγ)-selective inverse agonists with a phenanthridin-6(5H)-one skeleton from a liver X receptor ligand.,  22  (9): [PMID:24702856] [10.1016/j.bmc.2014.03.007]

2. 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