(8R,9S,10S,13S,14S,17S)-17-hydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-4H-cyclopenta[a]phenanthren-4-one

ID: ALA5287480

Max Phase: Preclinical

Molecular Formula: C19H28O3

Molecular Weight: 304.43

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CC=C4C(=O)CCC[C@@]43CO)[C@@H]1CC[C@@H]2O

Standard InChI:  InChI=1S/C19H28O3/c1-18-10-8-14-12(13(18)6-7-17(18)22)4-5-15-16(21)3-2-9-19(14,15)11-20/h5,12-14,17,20,22H,2-4,6-11H2,1H3/t12-,13-,14-,17-,18-,19-/m0/s1

Standard InChI Key:  TWEHLHPJCDGZDQ-GINZOMEDSA-N

Molfile:  

 
     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -0.9884   -0.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2779    0.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4430   -0.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1521    0.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1401    1.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9212    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1676    2.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4147    0.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9397    0.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2139    1.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174    1.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2876    1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029   -0.4949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4549   -0.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -1.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9750   -0.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -1.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4027   -0.9687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4147   -0.1449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7057    0.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -2.1962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1301   -0.7785    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8629    0.8940    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1064    0.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8732    0.9880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  6  5  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9  4  1  0
  5 10  1  1
  5 11  1  0
 11 12  1  0
 12  2  1  0
  4 13  1  6
 14  3  1  0
 14 15  1  0
 15 16  2  0
 16  1  1  0
 17 16  1  0
 18 17  1  0
 18 19  1  0
 19 20  1  0
 20  1  1  0
 17 21  2  0
  3 22  1  1
  2 23  1  6
  1 24  1  1
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5287480

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 304.43

Molecular Weight (Monoisotopic): 304.2038

AlogP: 2.85

#Rotatable Bonds: 1

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.24

CX LogD: 2.24

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.78

Np Likeness Score: 2.59

References

1. Adhikari N, Baidya SK, Jha T..  (2020)  Effective anti-aromatase therapy to battle against estrogen-mediated breast cancer: Comparative SAR/QSAR assessment on steroidal aromatase inhibitors.,  208  [PMID:33017749] [10.1016/j.ejmech.2020.112845]

Source

Source(1):

• Scientific Literature