(8R,9S,10R,11S,13S,14S,17S)-17-acetyl-11,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

ID: ALA5077912

PubChem CID: 68132252

Max Phase: Preclinical

Molecular Formula: C23H32O4

Molecular Weight: 372.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@]1(C(C)=O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3[C@@H](C)C[C@@]21C

Standard InChI:  InChI=1S/C23H32O4/c1-13-12-22(4)20(9-10-23(22,14(2)24)27-15(3)25)19-7-5-16-11-17(26)6-8-18(16)21(13)19/h11,13,18-21H,5-10,12H2,1-4H3/t13-,18-,19-,20-,21+,22-,23+/m0/s1

Standard InChI Key:  IWSXBCZCPVUWHT-GFNZRIEASA-N

Molfile:  

 
     RDKit          2D

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   14.1523  -12.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1564  -12.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8620  -12.5267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8434  -14.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8434  -15.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5487  -15.6133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5487  -13.9789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2540  -14.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2505  -15.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9526  -15.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6626  -15.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9595  -13.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6622  -14.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6790  -12.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9648  -13.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3817  -13.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3728  -13.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1440  -14.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6296  -13.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2467  -13.5745    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.6541  -13.5827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9525  -14.8002    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3681  -14.8168    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1363  -15.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2612  -12.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3763  -12.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5718  -12.9317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2774  -12.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5759  -13.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8579  -11.7095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4425  -11.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  3  2  1  0
  4  5  1  0
  4  7  1  0
  5  6  1  0
  6  9  2  0
  8  7  1  0
  8  9  1  0
  8 12  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12 13  1  0
 12 15  1  0
 13 17  1  0
 16 14  1  0
 14 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19  2  1  0
  2 16  1  0
  8 20  1  1
 13 21  1  1
 12 22  1  6
 17 23  1  6
  5 24  2  0
 15 25  1  1
 16 26  1  1
  3 27  1  0
 27 28  1  0
 27 29  2  0
  1 30  2  0
  1 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5077912

   [(8R,9S,10R,11S,13S,14S,17S)-17-acetyl-11,13-dimethyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 372.51

Molecular Weight (Monoisotopic): 372.2301

AlogP: 4.27

#Rotatable Bonds: 2

Polar Surface Area: 60.44

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: 2.13

References

1. Kurohara T, Ito T, Tsuji G, Misawa T, Yokoo H, Yanase Y, Shoda T, Sakai T, Hosoe J, Uchiyama N, Akiyama H, Demizu Y..  (2021)  Synthesis of Norgestomet and its 17β-isomer and evaluation of their agonistic activities against progesterone receptor.,  49  [PMID:34607200] [10.1016/j.bmc.2021.116425]

Source

Source(1):

• Scientific Literature