3,17-Dihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-15-carboxylic acid ethyl ester

ID: ALA2068189

PubChem CID: 11110713

Max Phase: Preclinical

Molecular Formula: C21H28O4

Molecular Weight: 344.45

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H28O4/c1-3-25-20(24)17-11-18(23)21(2)9-8-15-14-7-5-13(22)10-12(14)4-6-16(15)19(17)21/h5,7,10,15-19,22-23H,3-4,6,8-9,11H2,1-2H3/t15-,16-,17+,18+,19-,21-/m1/s1

Standard InChI Key:  RJNYQSQECGBATN-HDZJJSNZSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
    9.8018   -5.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8039   -5.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0868   -6.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5858   -6.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3780   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6547   -6.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0690   -5.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5891   -4.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8454   -6.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6526   -7.1344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0909   -4.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3800   -5.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0848   -7.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9458   -5.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3739   -7.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9418   -7.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3042   -7.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2205   -7.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2225   -6.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8650   -4.0206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6545   -7.0861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8059   -4.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4848   -7.5192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9140   -7.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7231   -8.0352    0.0000 C   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
  4  1  1  0
  5  3  1  0
  6  5  1  0
  7  4  1  0
  8  2  1  0
  4  9  1  6
 10 15  1  0
 11  2  1  0
 12  5  1  0
 13  3  1  0
 14  6  2  0
 15 13  1  0
 16 10  2  0
 17  9  2  0
 18 16  1  0
 19 14  1  0
  8 20  1  1
 21  9  1  0
  2 22  1  1
 23 18  1  0
 24 21  1  0
 25 24  1  0
  7  8  1  0
 12 11  1  0
 10  6  1  0
 18 19  2  0
  2  1  1  0
  3  1  1  0
  5 26  1  6
  3 27  1  1
  1 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2068189

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

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: 344.45

Molecular Weight (Monoisotopic): 344.1988

AlogP: 3.40

#Rotatable Bonds: 2

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: 10.33

CX Basic pKa: ┄

CX LogP: 3.47

CX LogD: 3.47

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.81

Np Likeness Score: 1.70

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