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

ID: ALA1628169

PubChem CID: 53322910

Max Phase: Preclinical

Molecular Formula: C22H33NO3

Molecular Weight: 359.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCO[C@@H]1Cc2cc(O)ccc2[C@H]2CC[C@]3(C)[C@@H](O)CC[C@H]3[C@@H]21

Standard InChI:  InChI=1S/C22H33NO3/c1-22-9-8-17-16-5-4-15(24)12-14(16)13-19(26-11-10-23(2)3)21(17)18(22)6-7-20(22)25/h4-5,12,17-21,24-25H,6-11,13H2,1-3H3/t17-,18+,19-,20+,21-,22+/m1/s1

Standard InChI Key:  VQVXGGVEIYVKNM-VTJFTLGMSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  1  0  0  0  0  0999 V2000
    6.8958   -4.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -4.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -3.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833   -4.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7417   -4.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7458   -5.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1833   -5.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -3.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917   -4.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -4.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6958   -3.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -5.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1917   -3.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8958   -5.8458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -5.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -4.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6083   -7.9083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8958   -2.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917   -2.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5958   -5.8458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8958   -6.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6083   -7.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8958   -8.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3292   -8.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -3.7708    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500   -5.0083    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -5.0083    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0
  5  2  1  0
  6  8  1  0
  7  4  1  0
  8  7  1  0
  9  3  1  0
 10  2  1  0
 11  1  1  0
 12  5  2  0
 13  3  1  0
 14  6  2  0
 15 11  1  0
  7 16  1  6
 17 14  1  0
 18 12  1  0
 19 24  1  0
  3 20  1  1
 13 21  1  1
 22 17  1  0
 23 16  1  0
 24 23  1  0
 25 19  1  0
 26 19  1  0
 15 13  1  0
  9 10  1  0
  5  6  1  0
 18 17  2  0
  4 27  1  1
  2  4  1  0
  2 28  1  6
  3  1  1  0
  1 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1628169

   (7R,8R,9S,13S,14S,17S)-7-[2-(dimethylamino)ethoxy]-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: 359.51

Molecular Weight (Monoisotopic): 359.2460

AlogP: 3.17

#Rotatable Bonds: 4

Polar Surface Area: 52.93

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.29

CX Basic pKa: 8.85

CX LogP: 2.88

CX LogD: 1.62

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.87

Np Likeness Score: 1.68

References

1. Poupaert JH, Lambert DM, Vamecq J, Abul-Hajj YJ.  (1995)  Molecular modeling studies on 11-aminoethoxyphenyl and 7-aminoethoxyphenyl estradiols. evidence suggesting a common hydrophobic pocket in estrogen receptor,  5  (8): [10.1016/0960-894X(95)00128-G]

Source

Source(1):

• Scientific Literature