(8R,12S,16R)-6-(S)-Cyclopropyl-10,13-dimethyl-17-pyridin-3-yl-1,2,6,7,8,9,10,11,12,13,14,15-dodecahydro-cyclopenta[a]phenanthren-3-one

ID: ALA3952352

PubChem CID: 68086786

Max Phase: Preclinical

Molecular Formula: C27H33NO

Molecular Weight: 387.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CCC(=O)C=C1C(C1CC1)C[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12

Standard InChI:  InChI=1S/C27H33NO/c1-26-12-10-24-21(23(26)8-7-22(26)18-4-3-13-28-16-18)15-20(17-5-6-17)25-14-19(29)9-11-27(24,25)2/h3-4,7,13-14,16-17,20-21,23-24H,5-6,8-12,15H2,1-2H3/t20?,21-,23-,24-,26+,27+/m0/s1

Standard InChI Key:  USRBOMURRWIDMU-SWOMEXEWSA-N

Molfile:  

     RDKit          2D

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    2.4691  -25.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7720  -27.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0807  -26.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3677  -22.9342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5960  -27.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7646  -26.2113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8685  -26.5877    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825  -25.3536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7638  -23.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942  -28.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2916  -24.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4839  -27.4296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3103  -28.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0705  -24.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1764  -26.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5610  -25.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635  -27.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679  -24.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8752  -25.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8110  -22.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5740  -24.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838  -27.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2911  -26.5752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1222  -23.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3694  -24.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1576  -25.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890  -28.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2989  -25.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 29  1  1
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  4 20  1  0
  7 12  1  0
  7  6  1  0
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 17 28  2  0
 32 13  1  0
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 23 18  1  0
  5 24  2  0
 26 14  2  0
 11 17  1  0
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  1 10  1  1
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  3 21  2  0
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  8  3  1  0
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  1 23  1  0
  1 32  1  0
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 32  4  1  0
  6  1  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3952352

   (8R,9S,10R,13S,14S)-6-cyclopropyl-10,13-dimethyl-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: 387.57

Molecular Weight (Monoisotopic): 387.2562

AlogP: 6.24

#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: 5.09

CX LogD: 5.09

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.60

Np Likeness Score: 1.77

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