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

ID: ALA1628159

PubChem CID: 10760896

Max Phase: Preclinical

Molecular Formula: C22H27ClO2

Molecular Weight: 358.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C[C@H]1C[C@@]2(C)[C@@H](CC[C@@]2(O)/C=C\Cl)[C@@H]2CCc3cc(O)ccc3[C@H]21

Standard InChI:  InChI=1S/C22H27ClO2/c1-3-14-13-21(2)19(8-9-22(21,25)10-11-23)18-6-4-15-12-16(24)5-7-17(15)20(14)18/h3,5,7,10-12,14,18-20,24-25H,1,4,6,8-9,13H2,2H3/b11-10-/t14-,18-,19-,20+,21-,22+/m0/s1

Standard InChI Key:  SSQWPMLTYOGGLM-XITZMQDRSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
    9.8093   -5.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0808   -6.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7994   -5.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3722   -5.8910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3706   -5.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6594   -6.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0892   -4.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5852   -4.8193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6609   -7.1367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0824   -7.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5819   -6.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4073   -4.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9393   -5.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6563   -4.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3752   -7.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0660   -5.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9423   -7.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9885   -4.2345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6548   -3.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2394   -7.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8521   -4.0368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2379   -6.3173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7964   -4.2442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9813   -3.4124    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.5209   -7.5517    0.0000 O   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  5  1  0
  5  7  1  0
  6  4  1  0
  7  1  1  0
  8  1  1  0
  9  6  2  0
 10  2  1  0
 11  3  1  0
  8 12  1  0
 13  6  1  0
  5 14  1  1
 15 10  1  0
 16  8  1  0
 17  9  1  0
 18 12  2  0
 19 14  2  0
 20 22  1  0
  8 21  1  1
 22 13  2  0
  1 23  1  1
 24 18  1  0
 25 20  1  0
 11 16  1  0
  4  2  1  0
  9 15  1  0
 17 20  2  0
  4 26  1  6
  2 27  1  1
  3 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1628159

   (8S,9S,11R,13S,14S,17R)-17-[(Z)-2-chloroethenyl]-11-ethenyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[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: 358.91

Molecular Weight (Monoisotopic): 358.1700

AlogP: 5.14

#Rotatable Bonds: 2

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.30

CX Basic pKa: ┄

CX LogP: 5.15

CX LogD: 5.14

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.72

Np Likeness Score: 1.77

References

1. Hanson RN, Napolitano E, Fiaschi R..  (1998)  Synthesis and evaluation of 11beta-substituted 21-chloro/iodo-(17alpha,20E/Z)-19-norpregna-1,3,5(10),20-te traene-3, 17beta-diols: high-affinity ligands for the estrogen receptor.,  41  (24): [PMID:9822539] [10.1021/jm9801051]

Source

Source(1):

• Scientific Literature