(11S,13S,16R,17S)-11-Ethyl-13-methyl-17-prop-1-ynyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,16,17-triol

ID: ALA1628177

PubChem CID: 10021042

Max Phase: Preclinical

Molecular Formula: C23H30O3

Molecular Weight: 354.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC#C[C@]1(O)[C@H](O)C[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3[C@@H](CC)C[C@@]21C

Standard InChI:  InChI=1S/C23H30O3/c1-4-10-23(26)20(25)12-19-18-8-6-15-11-16(24)7-9-17(15)21(18)14(5-2)13-22(19,23)3/h7,9,11,14,18-21,24-26H,5-6,8,12-13H2,1-3H3/t14-,18-,19-,20+,21+,22-,23-/m0/s1

Standard InChI Key:  FWNPTFPKAIDNJE-WZRDEOCJSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  1  0  0  0  0  0999 V2000
    9.7999   -5.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7991   -5.8865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5852   -4.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0811   -6.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3679   -5.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0866   -4.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6581   -6.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3727   -5.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5784   -6.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0624   -5.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3831   -4.6024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6616   -7.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0929   -7.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1686   -4.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9449   -5.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3749   -7.5403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9519   -7.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8523   -4.0347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7964   -4.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2387   -7.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2352   -6.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8862   -5.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6594   -4.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5247   -7.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9665   -4.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6601   -3.8235    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  1  1  0
  3  1  1  0
  4  2  1  0
  5  8  1  0
  6  1  1  0
  7  5  1  0
  8  6  1  0
  9  2  1  0
 10  3  1  0
  3 11  1  6
 12  7  2  0
 13  4  1  0
 14 11  3  0
 15  7  1  0
 16 13  1  0
 17 12  1  0
  3 18  1  1
  1 19  1  1
 20 21  1  0
 21 15  2  0
 10 22  1  6
  8 23  1  1
 24 20  1  0
 25 14  1  0
 26 23  1  0
 10  9  1  0
  4  5  1  0
 16 12  1  0
 20 17  2  0
  5 27  1  6
  4 28  1  1
  2 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1628177

   (8S,9S,11S,13S,14S,16R,17S)-11-ethyl-13-methyl-17-prop-1-ynyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,16,17-triol

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: 354.49

Molecular Weight (Monoisotopic): 354.2195

AlogP: 3.61

#Rotatable Bonds: 1

Polar Surface Area: 60.69

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.31

CX Basic pKa: ┄

CX LogP: 4.39

CX LogD: 4.39

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.68

Np Likeness Score: 1.93

References

1. Napolitano E, Fiaschi R, Carlson KE, Katzenellenbogen JA..  (1995)  11 beta-Substituted estradiol derivatives, potential high-affinity carbon-11-labeled probes for the estrogen receptor: a structure-affinity relationship study.,  38  (3): [PMID:7853335] [10.1021/jm00003a005]

Source

Source(1):

• Scientific Literature