(8R,9S,10R,13S,14S)-4,10,13-trimethyl-17-(pyridin-3-yl)-2,3,6,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

ID: ALA3980640

PubChem CID: 68087230

Max Phase: Preclinical

Molecular Formula: C25H33NO

Molecular Weight: 363.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C2CC[C@@H]3[C@H](CC[C@]4(C)C(c5cccnc5)=CC[C@@H]34)[C@@]2(C)CCC1O

Standard InChI:  InChI=1S/C25H33NO/c1-16-19-7-6-18-21-9-8-20(17-5-4-14-26-15-17)25(21,3)12-10-22(18)24(19,2)13-11-23(16)27/h4-5,8,14-15,18,21-23,27H,6-7,9-13H2,1-3H3/t18-,21-,22-,23?,24-,25+/m0/s1

Standard InChI Key:  LWWBEZGYTBIWMC-RVMXIGQUSA-N

Molfile:  

     RDKit          2D

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    8.9240  -23.6946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2116  -24.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3490  -23.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7803  -23.7169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3543  -22.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6364  -24.1157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5420  -20.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5699  -22.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8334  -21.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5554  -23.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6328  -24.9410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3418  -24.5241    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.9079  -20.9185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0504  -23.2986    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2116  -24.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2821  -21.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9240  -25.3454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0458  -23.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6442  -21.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0757  -22.4772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3419  -25.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0587  -24.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3585  -20.2961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6290  -23.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0591  -24.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7854  -22.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5674  -22.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5023  -25.3541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7727  -24.5362    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9250  -26.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 26  1  0
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  7 16  2  0
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  6  1  1  0
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  6 11  1  0
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  8  9  1  0
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  4 10  1  0
  2  1  1  0
  9 19  2  0
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  3  5  1  0
  6 24  1  1
  3 12  1  6
  6  3  1  0
 21 25  1  0
  2 15  1  0
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 26  4  1  0
 15 28  1  0
  4 29  1  6
 17 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3980640

   (8R,9S,10R,13S,14S)-4,10,13-trimethyl-17-pyridin-3-yl-2,3,6,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol

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: 363.55

Molecular Weight (Monoisotopic): 363.2562

AlogP: 5.79

#Rotatable Bonds: 1

Polar Surface Area: 33.12

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.81

CX LogP: 4.36

CX LogD: 4.36

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: 1.88

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