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

ID: ALA1628139

PubChem CID: 53325022

Max Phase: Preclinical

Molecular Formula: C21H29FO2

Molecular Weight: 332.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H29FO2/c1-21-12-14(3-2-10-22)20-16-7-5-15(23)11-13(16)4-6-17(20)18(21)8-9-19(21)24/h5,7,11,14,17-20,23-24H,2-4,6,8-10,12H2,1H3/t14-,17-,18-,19-,20+,21-/m0/s1

Standard InChI Key:  AZWLSFPATQHTLI-NWSAAYAGSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  1  0  0  0  0  0999 V2000
    9.7959   -5.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0868   -6.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7964   -5.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3766   -5.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6668   -6.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0857   -4.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3634   -5.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6674   -7.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0957   -7.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5718   -6.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9311   -5.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5787   -4.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3776   -7.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9576   -7.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0589   -5.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2348   -7.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2344   -6.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8080   -4.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8415   -4.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6406   -4.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4939   -5.0923    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5209   -7.5472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2079   -4.6755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9307   -5.0881    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 24  1  0
 24 20  1  0
 15 10  1  0
  4  2  1  0
 13  8  1  0
 14 16  2  0
  4 25  1  6
  2 26  1  1
  3 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1628139

   (8S,9S,11S,13S,14S,17S)-11-(3-fluoropropyl)-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: 332.46

Molecular Weight (Monoisotopic): 332.2152

AlogP: 4.59

#Rotatable Bonds: 3

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: 4.38

CX LogD: 4.38

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.85

Np Likeness Score: 1.85

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