2,2,2-trifluoro-N-((8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)acetamide

ID: ALA4520455

PubChem CID: 9885452

Max Phase: Preclinical

Molecular Formula: C20H22F3NO2

Molecular Weight: 365.39

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@@H]3c4ccc(NC(=O)C(F)(F)F)cc4CC[C@H]3[C@@H]1CCC2=O

Standard InChI:  InChI=1S/C20H22F3NO2/c1-19-9-8-14-13-5-3-12(24-18(26)20(21,22)23)10-11(13)2-4-15(14)16(19)6-7-17(19)25/h3,5,10,14-16H,2,4,6-9H2,1H3,(H,24,26)/t14-,15-,16+,19+/m1/s1

Standard InChI Key:  NSTVTTJIJMWDHI-JEWRLFTDSA-N

Molfile:  

 
     RDKit          2D

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   18.6578  -15.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6566  -16.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3647  -16.6437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3629  -15.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0715  -15.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0704  -16.2322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7766  -16.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4884  -16.2342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7789  -15.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4854  -15.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4965  -13.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7813  -14.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2030  -14.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1971  -15.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9717  -15.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4564  -14.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9813  -13.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2394  -13.1724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1962  -13.3763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9486  -16.6427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2412  -16.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5332  -16.6416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2419  -15.4164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8258  -16.2325    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.5325  -17.4588    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.8197  -17.0455    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.1921  -15.8238    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.7723  -15.8155    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.4781  -14.5980    0.0000 H   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  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  9 12  1  0
 10 14  1  0
 13 11  1  0
 11 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 17 18  2  0
 13 19  1  1
  2 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 22 25  1  0
 22 26  1  0
 14 27  1  6
  9 28  1  6
 10 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4520455

   2,2,2-trifluoro-N-[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]acetamide

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: 365.39

Molecular Weight (Monoisotopic): 365.1603

AlogP: 4.61

#Rotatable Bonds: 1

Polar Surface Area: 46.17

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.91

CX Basic pKa: ┄

CX LogP: 4.98

CX LogD: 4.98

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: 0.59

References

1. Saha T, Makar S, Swetha R, Gutti G, Singh SK..  (2019)  Estrogen signaling: An emanating therapeutic target for breast cancer treatment.,  177  [PMID:31129450] [10.1016/j.ejmech.2019.05.023]

Source

Source(1):

• Scientific Literature