(10R,13S)-10,13-dimethyl-6-phenyl-17-(pyridin-3-yl)-6,7,8,9,10,11,12,13,14,15-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

ID: ALA3982901

PubChem CID: 68087033

Max Phase: Preclinical

Molecular Formula: C30H33NO

Molecular Weight: 423.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CCC(=O)C=C1C(c1ccccc1)C[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12

Standard InChI:  InChI=1S/C30H33NO/c1-29-15-13-27-24(26(29)11-10-25(29)21-9-6-16-31-19-21)18-23(20-7-4-3-5-8-20)28-17-22(32)12-14-30(27,28)2/h3-10,16-17,19,23-24,26-27H,11-15,18H2,1-2H3/t23?,24-,26-,27-,29+,30+/m0/s1

Standard InChI Key:  SFHFDQKHSWEYGO-WWBNFFIRSA-N

Molfile:  

     RDKit          2D

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   11.3049  -24.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6053  -25.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9343  -24.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2252  -21.6362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4437  -25.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7309  -26.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5979  -24.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7094  -25.3079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4302  -24.0661    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   14.1418  -23.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3199  -26.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9239  -23.3839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1718  -22.5970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8942  -26.1661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.7161  -24.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6674  -21.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4215  -23.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0223  -25.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1413  -25.2952    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9774  -22.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2204  -22.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9959  -24.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1492  -24.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0219  -27.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0258  -28.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7430  -28.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4577  -28.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4501  -27.3659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 28  1  1
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  5 23  2  0
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  1 10  1  1
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  3 20  2  0
 17 29  1  1
 15 13  1  0
 25  7  1  0
 27  5  1  0
  8  3  1  0
 15 16  1  0
 18 11  2  0
 21 22  1  0
  1 22  1  0
  1 30  1  0
 13 24  1  0
 30  4  1  0
  6  1  1  0
 12 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3982901

   (8R,9S,10R,13S,14S)-10,13-dimethyl-6-phenyl-17-pyridin-3-yl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one

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: 423.60

Molecular Weight (Monoisotopic): 423.2562

AlogP: 7.00

#Rotatable Bonds: 2

Polar Surface Area: 29.96

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.81

CX LogP: 5.95

CX LogD: 5.95

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: 1.50

References

1.  (2013)  C-17-heteroaryl steroidal compounds as inhibitors of CYP11B, CYP17, and/or CYP21, 

2. Blass, Benjamin E BE and 18 more authors.  2016-12-01  Design, synthesis, and evaluation of (2S,4R)-Ketoconazole sulfonamide analogs as potential treatments for Metabolic Syndrome.  [PMID:27789139]

3. Fehl, Charlie C and 5 more authors.  2018-06-14  Structure-Based Design of Inhibitors with Improved Selectivity for Steroidogenic Cytochrome P450 17A1 over Cytochrome P450 21A2.  [PMID:29792703]

Source

Source(1):

• Patent Bioactivity Data