(11S,13S,17S)-11-((E)-2-Iodo-vinyl)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

ID: ALA2092908

PubChem CID: 10047961

Max Phase: Preclinical

Molecular Formula: C20H25IO2

Molecular Weight: 424.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12C[C@H](/C=C\I)[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1CC[C@@H]2O

Standard InChI:  InChI=1S/C20H25IO2/c1-20-11-13(8-9-21)19-15-5-3-14(22)10-12(15)2-4-16(19)17(20)6-7-18(20)23/h3,5,8-10,13,16-19,22-23H,2,4,6-7,11H2,1H3/b9-8-/t13-,16-,17-,18-,19+,20-/m0/s1

Standard InChI Key:  BLGSUUFKFHIHOU-AMHJZTKYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  1  0  0  0  0  0999 V2000
    9.8096   -5.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1012   -6.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8111   -5.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3897   -5.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3755   -5.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6797   -6.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0981   -4.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6810   -7.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1108   -7.1377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5874   -6.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9641   -5.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5929   -4.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6516   -4.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3924   -7.5514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9710   -7.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0743   -5.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6503   -3.8475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2471   -7.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2457   -6.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8208   -4.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8551   -4.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328   -7.5628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3809   -6.7281    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0946   -5.4885    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8084   -6.7322    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3632   -3.4324    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  5  1  0
  5  7  1  0
  6  4  1  0
  7  1  1  0
  8  6  2  0
  9  2  1  0
 10  3  1  0
 11  6  1  0
 12  1  1  0
  5 13  1  1
 14  9  1  0
 15  8  1  0
 16 12  1  0
 17 13  2  0
 18 19  1  0
 19 11  2  0
  1 20  1  1
 12 21  1  1
 22 18  1  0
 16 10  1  0
  4  2  1  0
 14  8  1  0
 15 18  2  0
  4 23  1  6
  2 24  1  1
  3 25  1  6
 17 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2092908

   (8S,9R,11S,13S,14S,17S)-11-[(Z)-2-iodoethenyl]-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: 424.32

Molecular Weight (Monoisotopic): 424.0899

AlogP: 4.78

#Rotatable Bonds: 1

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: 10.30

CX Basic pKa: ┄

CX LogP: 4.74

CX LogD: 4.74

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: 2.03

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