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

ID: ALA2068018

PubChem CID: 70684478

Max Phase: Preclinical

Molecular Formula: C21H28O4

Molecular Weight: 344.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@H]3[C@@H]1[C@@H](CCC(=O)O)CC2O

Standard InChI:  InChI=1S/C21H28O4/c1-21-9-8-16-15-6-4-14(22)10-12(15)2-5-17(16)20(21)13(11-18(21)23)3-7-19(24)25/h4,6,10,13,16-18,20,22-23H,2-3,5,7-9,11H2,1H3,(H,24,25)/t13-,16+,17+,18?,20-,21+/m0/s1

Standard InChI Key:  KUIIGYWWSATEKH-VGZQISJJSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
    9.8057   -5.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0857   -6.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8043   -5.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3768   -5.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6541   -6.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5881   -6.1435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5904   -4.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6527   -7.1346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0885   -4.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0665   -5.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3782   -5.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0844   -7.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9452   -5.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9091   -7.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3741   -7.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9425   -7.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8483   -6.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3685   -8.4811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6489   -7.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2211   -7.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2225   -6.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8573   -4.0152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8070   -4.2458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7180   -8.0269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4860   -7.5252    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 11  1  0
  5  4  1  0
  6  3  1  0
  7  1  1  0
  8  5  2  0
  9  1  1  0
 10  7  1  0
 11  9  1  0
 12  2  1  0
 13  5  1  0
 14 19  1  0
 15 12  1  0
 16  8  1  0
  6 17  1  6
 18 14  2  0
 19 17  1  0
 20 21  1  0
 21 13  2  0
 22  7  1  0
  1 23  1  1
 24 14  1  0
 25 20  1  0
 10  6  1  0
  4  2  1  0
 15  8  1  0
 20 16  2  0
  4 26  1  6
  2 27  1  1
  3 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2068018

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

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: 3.70

#Rotatable Bonds: 3

Polar Surface Area: 77.76

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.59

CX Basic pKa: ┄

CX LogP: 3.60

CX LogD: 0.86

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.78

Np Likeness Score: 1.99

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