(3,17-Dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-7-yl)-acetic acid ethyl ester

ID: ALA1628168

PubChem CID: 11810480

Max Phase: Preclinical

Molecular Formula: C22H30O4

Molecular Weight: 358.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)C[C@@H]1Cc2cc(O)ccc2[C@H]2CC[C@]3(C)[C@@H](O)CC[C@H]3[C@H]12

Standard InChI:  InChI=1S/C22H30O4/c1-3-26-20(25)12-14-10-13-11-15(23)4-5-16(13)17-8-9-22(2)18(21(14)17)6-7-19(22)24/h4-5,11,14,17-19,21,23-24H,3,6-10,12H2,1-2H3/t14-,17+,18-,19-,21+,22-/m0/s1

Standard InChI Key:  MDPSMJGFMAGIPN-KEKJONKRSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  1  0  0  0  0  0999 V2000
    6.9958   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -4.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9958   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -4.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375   -4.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8375   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -5.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -2.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7833   -4.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -4.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9833   -6.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7833   -3.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -5.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2625   -3.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -7.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000   -4.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9958   -2.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6958   -7.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500   -2.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -5.8125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6875   -7.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9750   -8.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2708   -3.7625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583   -4.9958    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0886   -4.9823    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
  7 13  1  6
 14 13  1  0
 15  3  1  0
 16  6  2  0
 17 11  1  0
 18 14  2  0
 19 16  1  0
 20 12  1  0
  3 21  1  1
 22 14  1  0
 15 23  1  1
 24 19  1  0
 25 22  1  0
 26 25  1  0
 17 15  1  0
 10  9  1  0
  6  5  1  0
 20 19  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:

   

   ALA1628168

   ethyl 2-[(7S,8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-yl]acetate

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: 358.48

Molecular Weight (Monoisotopic): 358.2144

AlogP: 3.79

#Rotatable Bonds: 3

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.70

CX Basic pKa: ┄

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.81

Np Likeness Score: 1.93

References

1. Labaree DC, Zhang JX, Harris HA, O'Connor C, Reynolds TY, Hochberg RB..  (2003)  Synthesis and evaluation of B-, C-, and D-ring-substituted estradiol carboxylic acid esters as locally active estrogens.,  46  (10): [PMID:12723952] [10.1021/jm0204340]

Source

Source(1):

• Scientific Literature