(8S,9S,10R,13S,14S)-17-(5-fluoropyridin-3-yl)-10,13-dimethyl-6-methylene-6,7,8,9,10,11,12,13,14,15-decahydro-3H-cyclopenta[a]phenanthren-3-one

ID: ALA3972568

PubChem CID: 68087029

Max Phase: Preclinical

Molecular Formula: C25H26FNO

Molecular Weight: 375.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C[C@@H]2[C@H](CC[C@]3(C)C(c4cncc(F)c4)=CC[C@@H]23)[C@@]2(C)C=CC(=O)C=C12

Standard InChI:  InChI=1S/C25H26FNO/c1-15-10-19-21-5-4-20(16-11-17(26)14-27-13-16)24(21,2)9-7-22(19)25(3)8-6-18(28)12-23(15)25/h4,6,8,11-14,19,21-22H,1,5,7,9-10H2,2-3H3/t19-,21-,22-,24+,25+/m0/s1

Standard InChI Key:  LDVWQQQAVALZQA-WRUJZFPBSA-N

Molfile:  

     RDKit          2D

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   11.9441   -3.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6838   -4.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1573   -5.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6688   -5.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8923   -5.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1783   -6.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1714   -6.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4574   -7.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4783   -5.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4882   -4.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1981   -4.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9022   -4.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9991   -4.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7742   -5.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4720   -6.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1736   -5.3200    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8876   -6.5540    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7599   -6.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7644   -6.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0638   -5.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3541   -6.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3496   -6.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0547   -7.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6392   -7.3361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4471   -8.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7418   -3.7454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0021   -2.9738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4631   -2.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6605   -2.5255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4039   -3.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1182   -1.9142    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  2  0
  4  3  1  0
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  6  5  1  0
  7  6  1  0
  8  7  1  0
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  9 19  1  0
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 12 11  1  0
  2 12  1  0
  5 12  1  0
 12 13  1  1
  6  9  1  0
 19 14  1  1
  9 15  1  6
  6 16  1  1
  5 17  1  6
 18 19  1  0
 18 23  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
  8 25  2  0
  1 26  2  0
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 29 30  2  0
 30  1  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3972568

   (8S,9S,10R,13S,14S)-17-(5-fluoropyridin-3-yl)-10,13-dimethyl-6-methylidene-8,9,11,12,14,15-hexahydro-7H-cyclopenta[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: 375.49

Molecular Weight (Monoisotopic): 375.1998

AlogP: 5.69

#Rotatable Bonds: 1

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: 2.40

CX LogP: 4.61

CX LogD: 4.61

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: 1.59

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