(5S,11R)-5,11-Dimethyl-5,6,11,12-tetrahydro-chrysene-2,8-diol

ID: ALA2114182

PubChem CID: 10541681

Max Phase: Preclinical

Molecular Formula: C20H20O2

Molecular Weight: 292.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1Cc2cc(O)ccc2C2=C1c1ccc(O)cc1C[C@H]2C

Standard InChI:  InChI=1S/C20H20O2/c1-11-7-13-9-15(21)4-6-18(13)20-12(2)8-14-10-16(22)3-5-17(14)19(11)20/h3-6,9-12,21-22H,7-8H2,1-2H3/t11-,12-/m1/s1

Standard InChI Key:  KZUYEPBUFHNSDS-VXGBXAGGSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  1  0  0  0  0  0999 V2000
    5.7542   -4.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4667   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -4.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -5.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -5.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -2.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -5.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -4.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9042   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292   -5.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9042   -2.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6167   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -5.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6167   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -5.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417   -2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -5.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3417   -2.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  9  1  0
  6  3  1  0
  7  2  1  0
  8  1  1  0
  9  8  1  0
 10  6  1  0
 11  3  2  0
 12  4  1  0
 13  6  2  0
 14  5  1  0
 15 14  2  0
 16 17  2  0
 17 11  1  0
 18 12  2  0
  7 19  1  6
  8 20  1  6
 21 16  1  0
 22 15  1  0
  4  5  2  0
  7 10  1  0
 16 13  1  0
 18 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2114182

   (5R,11R)-5,11-dimethyl-5,6,11,12-tetrahydrochrysene-2,8-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: 292.38

Molecular Weight (Monoisotopic): 292.1463

AlogP: 4.39

#Rotatable Bonds: ┄

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: 8.69

CX Basic pKa: ┄

CX LogP: 4.98

CX LogD: 4.96

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: 0.83

References

1. Meyers MJ, Sun J, Carlson KE, Katzenellenbogen BS, Katzenellenbogen JA..  (1999)  Estrogen receptor subtype-selective ligands: asymmetric synthesis and biological evaluation of cis- and trans-5,11-dialkyl- 5,6,11, 12-tetrahydrochrysenes.,  42  (13): [PMID:10395487] [10.1021/jm990101b]

Source

Source(1):

• Scientific Literature