1-((2R,3aS,3a1R,4aR,4a1S,5aS,6S,8aS,8bS)-2-hydroxy-3a1,5a-dimethyl-3,3a,3a1,4a,4a1,5,5a,6,7,8,8a,8b,9,10-tetradecahydro-2H-cyclopenta[1,2]phenanthro[4,5-bcd]furan-6-yl)ethan-1-one

ID: ALA5285617

Max Phase: Preclinical

Molecular Formula: C21H30O3

Molecular Weight: 330.47

Names and Identifiers

Canonical SMILES:  CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=C[C@H](O)C[C@@H]5O[C@H](C[C@]12C)[C@@H]3[C@]45C

Standard InChI:  InChI=1S/C21H30O3/c1-11(22)15-6-7-16-14-5-4-12-8-13(23)9-18-21(12,3)19(14)17(24-18)10-20(15,16)2/h8,13-19,23H,4-7,9-10H2,1-3H3/t13-,14-,15+,16-,17+,18-,19+,20+,21+/m0/s1

Standard InChI Key:  NLCQTQAUAJGNLL-FDKYLEAMSA-N

Molfile:  

 
     RDKit          2D

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   -1.6218   -0.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9073   -0.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9073   -1.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6218   -2.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3362   -1.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1928   -0.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2362    0.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361   -0.4028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5109    0.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5216    0.0098    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3264   -1.2231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276    1.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2538    1.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6702    2.0529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0509    1.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1927    1.2474    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  6 18  1  6
  3 19  1  1
 11 20  1  0
  2 20  1  6
  7 21  1  6
  8 22  1  1
 14 23  1  6
 13 24  1  1
 15 25  1  1
 25 26  2  0
 25 27  1  0
 11 28  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA5285617

   ---

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: 330.47

Molecular Weight (Monoisotopic): 330.2195

AlogP: 3.50

#Rotatable Bonds: 1

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.29

CX LogD: 2.29

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: 2.95

References

1. Blanco MJ, La D, Coughlin Q, Newman CA, Griffin AM, Harrison BL, Salituro FG..  (2018)  Breakthroughs in neuroactive steroid drug discovery.,  28  (2): [PMID:29223589] [10.1016/j.bmcl.2017.11.043]

Source

Source(1):

• Scientific Literature