(11S,13S,17S)-11-(4-Fluoro-butyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA1628172

PubChem CID: 53325563

Max Phase: Preclinical

Molecular Formula: C22H31FO2

Molecular Weight: 346.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12C[C@H](CCCCF)[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O

Standard InChI:  InChI=1S/C22H31FO2/c1-22-13-15(4-2-3-11-23)21-17-8-6-16(24)12-14(17)5-7-18(21)19(22)9-10-20(22)25/h6,8,12,15,18-21,24-25H,2-5,7,9-11,13H2,1H3/t15-,18-,19-,20-,21+,22-/m0/s1

Standard InChI Key:  FBEUVWACMBTMOT-USUWBSJTSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
    9.7979   -5.0741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0844   -6.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7945   -5.8956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3735   -5.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6675   -6.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0870   -4.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3642   -5.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6683   -7.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0894   -7.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5748   -6.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9312   -5.9132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5812   -4.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3793   -7.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9582   -7.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0621   -5.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2347   -7.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2339   -6.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8056   -4.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8398   -4.0327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6408   -4.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7691   -4.6791    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5119   -7.5444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4842   -5.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9263   -5.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2070   -4.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3667   -6.7167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -5.4792    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7917   -6.7208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  7  1  0
  5  4  1  0
  6  1  1  0
  7  6  1  0
  8  5  2  0
  9  2  1  0
 10  3  1  0
 11  5  1  0
 12  1  1  0
 13  9  1  0
 14  8  1  0
 15 12  1  0
 16 17  1  0
 17 11  2  0
  1 18  1  1
 12 19  1  1
  7 20  1  1
 21 23  1  0
 22 16  1  0
 23 25  1  0
 24 20  1  0
 25 24  1  0
 15 10  1  0
  2  4  1  0
 13  8  1  0
 14 16  2  0
  4 26  1  6
  2 27  1  1
  3 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1628172

   (8S,9S,11S,13S,14S,17S)-11-(4-fluorobutyl)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol

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: 346.49

Molecular Weight (Monoisotopic): 346.2308

AlogP: 4.98

#Rotatable Bonds: 4

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.31

CX Basic pKa: ┄

CX LogP: 4.82

CX LogD: 4.82

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: 1.84

References

1. Napolitano E, Fiaschi R, Carlson KE, Katzenellenbogen JA..  (1995)  11 beta-substituted estradiol derivatives. 2. Potential carbon-11- and iodine-labeled probes for the estrogen receptor.,  38  (14): [PMID:7629815] [10.1021/jm00014a028]

Source

Source(1):

• Scientific Literature